email plus return item statuses

2025-10-06 15:41:48 -04:00
parent 67cc997ddc
commit 5c3d505988
28 changed files with 5861 additions and 259 deletions
--- a/backend/config/aws.js
+++ b/backend/config/aws.js
@@ -0,0 +1,36 @@
+const { fromIni } = require("@aws-sdk/credential-providers");
+
+/**
+ * Get AWS configuration based on environment
+ * - Development: Uses AWS credential profiles from ~/.aws/credentials
+ * - Production: Uses IAM roles (EC2/Lambda/ECS instance roles)
+ */
+function getAWSCredentials() {
+  if (process.env.NODE_ENV === "dev") {
+    // Local development: use profile from ~/.aws/credentials
+    const profile = process.env.AWS_PROFILE;
+    return fromIni({ profile });
+  }
+}
+
+/**
+ * Get complete AWS client configuration
+ */
+function getAWSConfig() {
+  const config = {
+    region: process.env.AWS_REGION || "us-east-1",
+  };
+
+  const credentials = getAWSCredentials();
+
+  if (credentials) {
+    config.credentials = credentials;
+  }
+
+  return config;
+}
+
+module.exports = {
+  getAWSConfig,
+  getAWSCredentials,
+};
--- a/backend/jobs/conditionCheckReminder.js
+++ b/backend/jobs/conditionCheckReminder.js
@@ -0,0 +1,258 @@
+const cron = require("node-cron");
+const {
+  Rental,
+  User,
+  Item,
+  ConditionCheck,
+} = require("../models");
+const { Op } = require("sequelize");
+const emailService = require("../services/emailService");
+const logger = require("../utils/logger");
+
+const reminderSchedule = "0 * * * *"; // Run every hour
+
+class ConditionCheckReminderJob {
+  static startScheduledReminders() {
+    console.log("Starting automated condition check reminder job...");
+
+    const reminderJob = cron.schedule(
+      reminderSchedule,
+      async () => {
+        try {
+          await this.sendConditionCheckReminders();
+        } catch (error) {
+          logger.error("Error in scheduled condition check reminders", {
+            error: error.message,
+            stack: error.stack,
+          });
+        }
+      },
+      {
+        scheduled: false,
+        timezone: "America/New_York",
+      }
+    );
+
+    // Start the job
+    reminderJob.start();
+
+    console.log("Condition check reminder job scheduled:");
+    console.log("- Reminders every hour: " + reminderSchedule);
+
+    return {
+      reminderJob,
+
+      stop() {
+        reminderJob.stop();
+        console.log("Condition check reminder job stopped");
+      },
+
+      getStatus() {
+        return {
+          reminderJobRunning: reminderJob.getStatus() === "scheduled",
+        };
+      },
+    };
+  }
+
+  // Send reminders for upcoming condition check windows
+  static async sendConditionCheckReminders() {
+    try {
+      const now = new Date();
+      const reminderWindow = new Date(now.getTime() + 24 * 60 * 60 * 1000); // 24 hours ahead
+
+      // Find rentals with upcoming condition check windows
+      const rentals = await Rental.findAll({
+        where: {
+          status: {
+            [Op.in]: ["confirmed", "active", "completed"],
+          },
+        },
+        include: [
+          { model: User, as: "owner" },
+          { model: User, as: "renter" },
+          { model: Item, as: "item" },
+        ],
+      });
+
+      for (const rental of rentals) {
+        await this.checkAndSendConditionReminders(rental, now, reminderWindow);
+      }
+
+      console.log(
+        `Processed ${rentals.length} rentals for condition check reminders`
+      );
+    } catch (error) {
+      console.error("Error sending condition check reminders:", error);
+    }
+  }
+
+  // Check specific rental for reminder needs
+  static async checkAndSendConditionReminders(rental, now, reminderWindow) {
+    const rentalStart = new Date(rental.startDateTime);
+    const rentalEnd = new Date(rental.endDateTime);
+
+    // Pre-rental owner check (24 hours before rental start)
+    const preRentalWindow = new Date(
+      rentalStart.getTime() - 24 * 60 * 60 * 1000
+    );
+    if (now <= preRentalWindow && preRentalWindow <= reminderWindow) {
+      const existingCheck = await ConditionCheck.findOne({
+        where: {
+          rentalId: rental.id,
+          checkType: "pre_rental_owner",
+        },
+      });
+
+      if (!existingCheck) {
+        await this.sendPreRentalOwnerReminder(rental);
+      }
+    }
+
+    // Rental start renter check (within 24 hours of rental start)
+    if (now <= rentalStart && rentalStart <= reminderWindow) {
+      const existingCheck = await ConditionCheck.findOne({
+        where: {
+          rentalId: rental.id,
+          checkType: "rental_start_renter",
+        },
+      });
+
+      if (!existingCheck) {
+        await this.sendRentalStartRenterReminder(rental);
+      }
+    }
+
+    // Rental end renter check (within 24 hours of rental end)
+    if (now <= rentalEnd && rentalEnd <= reminderWindow) {
+      const existingCheck = await ConditionCheck.findOne({
+        where: {
+          rentalId: rental.id,
+          checkType: "rental_end_renter",
+        },
+      });
+
+      if (!existingCheck) {
+        await this.sendRentalEndRenterReminder(rental);
+      }
+    }
+
+    // Post-rental owner check (24 hours after rental end)
+    const postRentalWindow = new Date(
+      rentalEnd.getTime() + 24 * 60 * 60 * 1000
+    );
+    if (now <= postRentalWindow && postRentalWindow <= reminderWindow) {
+      const existingCheck = await ConditionCheck.findOne({
+        where: {
+          rentalId: rental.id,
+          checkType: "post_rental_owner",
+        },
+      });
+
+      if (!existingCheck) {
+        await this.sendPostRentalOwnerReminder(rental);
+      }
+    }
+  }
+
+  // Individual email senders
+  static async sendPreRentalOwnerReminder(rental) {
+    const notificationData = {
+      type: "condition_check_reminder",
+      subtype: "pre_rental_owner",
+      title: "Condition Check Reminder",
+      message: `Please take photos of "${rental.item.name}" before the rental begins tomorrow.`,
+      rentalId: rental.id,
+      userId: rental.ownerId,
+      metadata: {
+        checkType: "pre_rental_owner",
+        deadline: new Date(rental.startDateTime).toISOString(),
+      },
+    };
+
+    await emailService.sendConditionCheckReminder(
+      rental.owner.email,
+      notificationData,
+      rental
+    );
+
+    console.log(`Pre-rental owner reminder sent for rental ${rental.id}`);
+  }
+
+  static async sendRentalStartRenterReminder(rental) {
+    const notificationData = {
+      type: "condition_check_reminder",
+      subtype: "rental_start_renter",
+      title: "Condition Check Reminder",
+      message: `Please take photos when you receive "${rental.item.name}" to document its condition.`,
+      rentalId: rental.id,
+      userId: rental.renterId,
+      metadata: {
+        checkType: "rental_start_renter",
+        deadline: new Date(
+          rental.startDateTime.getTime() + 24 * 60 * 60 * 1000
+        ).toISOString(),
+      },
+    };
+
+    await emailService.sendConditionCheckReminder(
+      rental.renter.email,
+      notificationData,
+      rental
+    );
+
+    console.log(`Rental start renter reminder sent for rental ${rental.id}`);
+  }
+
+  static async sendRentalEndRenterReminder(rental) {
+    const notificationData = {
+      type: "condition_check_reminder",
+      subtype: "rental_end_renter",
+      title: "Condition Check Reminder",
+      message: `Please take photos when returning "${rental.item.name}" to document its condition.`,
+      rentalId: rental.id,
+      userId: rental.renterId,
+      metadata: {
+        checkType: "rental_end_renter",
+        deadline: new Date(
+          rental.endDateTime.getTime() + 24 * 60 * 60 * 1000
+        ).toISOString(),
+      },
+    };
+
+    await emailService.sendConditionCheckReminder(
+      rental.renter.email,
+      notificationData,
+      rental
+    );
+
+    console.log(`Rental end renter reminder sent for rental ${rental.id}`);
+  }
+
+  static async sendPostRentalOwnerReminder(rental) {
+    const notificationData = {
+      type: "condition_check_reminder",
+      subtype: "post_rental_owner",
+      title: "Condition Check Reminder",
+      message: `Please take photos and mark the return status for "${rental.item.name}".`,
+      rentalId: rental.id,
+      userId: rental.ownerId,
+      metadata: {
+        checkType: "post_rental_owner",
+        deadline: new Date(
+          rental.endDateTime.getTime() + 48 * 60 * 60 * 1000
+        ).toISOString(),
+      },
+    };
+
+    await emailService.sendConditionCheckReminder(
+      rental.owner.email,
+      notificationData,
+      rental
+    );
+
+    console.log(`Post-rental owner reminder sent for rental ${rental.id}`);
+  }
+}
+
+module.exports = ConditionCheckReminderJob;
--- a/backend/jobs/rentalStatusJob.js
+++ b/backend/jobs/rentalStatusJob.js
@@ -0,0 +1,101 @@
+const cron = require("node-cron");
+const { Rental } = require("../models");
+const { Op } = require("sequelize");
+const logger = require("../utils/logger");
+
+const statusUpdateSchedule = "*/15 * * * *"; // Run every 15 minutes
+
+class RentalStatusJob {
+  static startScheduledStatusUpdates() {
+    console.log("Starting automated rental status updates...");
+
+    const statusJob = cron.schedule(
+      statusUpdateSchedule,
+      async () => {
+        try {
+          await this.activateStartedRentals();
+        } catch (error) {
+          logger.error("Error in scheduled rental status update", {
+            error: error.message,
+            stack: error.stack
+          });
+        }
+      },
+      {
+        scheduled: false,
+        timezone: "America/New_York",
+      }
+    );
+
+    // Start the job
+    statusJob.start();
+
+    console.log("Rental status job scheduled:");
+    console.log("- Status updates every 15 minutes: " + statusUpdateSchedule);
+
+    return {
+      statusJob,
+
+      stop() {
+        statusJob.stop();
+        console.log("Rental status job stopped");
+      },
+
+      getStatus() {
+        return {
+          statusJobRunning: statusJob.getStatus() === "scheduled",
+        };
+      },
+    };
+  }
+
+  static async activateStartedRentals() {
+    try {
+      const now = new Date();
+
+      // Find all confirmed rentals where start time has arrived
+      const rentalsToActivate = await Rental.findAll({
+        where: {
+          status: "confirmed",
+          startDateTime: {
+            [Op.lte]: now,
+          },
+        },
+      });
+
+      if (rentalsToActivate.length === 0) {
+        return { activated: 0 };
+      }
+
+      // Update all matching rentals to active status
+      const rentalIds = rentalsToActivate.map((r) => r.id);
+      const [updateCount] = await Rental.update(
+        { status: "active" },
+        {
+          where: {
+            id: {
+              [Op.in]: rentalIds,
+            },
+          },
+        }
+      );
+
+      logger.info("Activated started rentals", {
+        count: updateCount,
+        rentalIds: rentalIds,
+      });
+
+      console.log(`Activated ${updateCount} rentals that have started`);
+
+      return { activated: updateCount, rentalIds };
+    } catch (error) {
+      logger.error("Error activating started rentals", {
+        error: error.message,
+        stack: error.stack,
+      });
+      throw error;
+    }
+  }
+}
+
+module.exports = RentalStatusJob;
--- a/backend/models/ConditionCheck.js
+++ b/backend/models/ConditionCheck.js
@@ -0,0 +1,53 @@
+const { DataTypes } = require("sequelize");
+const sequelize = require("../config/database");
+
+const ConditionCheck = sequelize.define("ConditionCheck", {
+  id: {
+    type: DataTypes.UUID,
+    defaultValue: DataTypes.UUIDV4,
+    primaryKey: true,
+  },
+  rentalId: {
+    type: DataTypes.UUID,
+    allowNull: false,
+    references: {
+      model: "Rentals",
+      key: "id",
+    },
+  },
+  checkType: {
+    type: DataTypes.ENUM(
+      "pre_rental_owner",
+      "rental_start_renter",
+      "rental_end_renter",
+      "post_rental_owner"
+    ),
+    allowNull: false,
+  },
+  photos: {
+    type: DataTypes.ARRAY(DataTypes.STRING),
+    defaultValue: [],
+  },
+  notes: {
+    type: DataTypes.TEXT,
+  },
+  submittedBy: {
+    type: DataTypes.UUID,
+    allowNull: false,
+    references: {
+      model: "Users",
+      key: "id",
+    },
+  },
+  submittedAt: {
+    type: DataTypes.DATE,
+    allowNull: false,
+    defaultValue: DataTypes.NOW,
+  },
+  metadata: {
+    type: DataTypes.JSONB,
+    defaultValue: {},
+  },
+});
+
+module.exports = ConditionCheck;
--- a/backend/models/Rental.js
+++ b/backend/models/Rental.js
@@ -57,7 +57,11 @@ const Rental = sequelize.define("Rental", {
      "confirmed",
      "active",
      "completed",
-      "cancelled"
+      "cancelled",
+      "returned_late",
+      "returned_late_and_damaged",
+      "damaged",
+      "lost"
    ),
    defaultValue: "pending",
  },
@@ -153,6 +157,29 @@ const Rental = sequelize.define("Rental", {
  renterPrivateMessage: {
    type: DataTypes.TEXT,
  },
+  // Condition check and return handling fields
+  actualReturnDateTime: {
+    type: DataTypes.DATE,
+  },
+  lateFees: {
+    type: DataTypes.DECIMAL(10, 2),
+    defaultValue: 0.0,
+  },
+  damageFees: {
+    type: DataTypes.DECIMAL(10, 2),
+    defaultValue: 0.0,
+  },
+  replacementFees: {
+    type: DataTypes.DECIMAL(10, 2),
+    defaultValue: 0.0,
+  },
+  itemLostReportedAt: {
+    type: DataTypes.DATE,
+  },
+  damageAssessment: {
+    type: DataTypes.JSONB,
+    defaultValue: {},
+  },
 });

 module.exports = Rental;
--- a/backend/models/index.js
+++ b/backend/models/index.js
@@ -1,41 +1,75 @@
-const sequelize = require('../config/database');
-const User = require('./User');
-const Item = require('./Item');
-const Rental = require('./Rental');
-const Message = require('./Message');
-const ItemRequest = require('./ItemRequest');
-const ItemRequestResponse = require('./ItemRequestResponse');
-const UserAddress = require('./UserAddress');
+const sequelize = require("../config/database");
+const User = require("./User");
+const Item = require("./Item");
+const Rental = require("./Rental");
+const Message = require("./Message");
+const ItemRequest = require("./ItemRequest");
+const ItemRequestResponse = require("./ItemRequestResponse");
+const UserAddress = require("./UserAddress");
+const ConditionCheck = require("./ConditionCheck");

-User.hasMany(Item, { as: 'ownedItems', foreignKey: 'ownerId' });
-Item.belongsTo(User, { as: 'owner', foreignKey: 'ownerId' });
+User.hasMany(Item, { as: "ownedItems", foreignKey: "ownerId" });
+Item.belongsTo(User, { as: "owner", foreignKey: "ownerId" });

-User.hasMany(Rental, { as: 'rentalsAsRenter', foreignKey: 'renterId' });
-User.hasMany(Rental, { as: 'rentalsAsOwner', foreignKey: 'ownerId' });
+User.hasMany(Rental, { as: "rentalsAsRenter", foreignKey: "renterId" });
+User.hasMany(Rental, { as: "rentalsAsOwner", foreignKey: "ownerId" });

-Item.hasMany(Rental, { as: 'rentals', foreignKey: 'itemId' });
-Rental.belongsTo(Item, { as: 'item', foreignKey: 'itemId' });
-Rental.belongsTo(User, { as: 'renter', foreignKey: 'renterId' });
-Rental.belongsTo(User, { as: 'owner', foreignKey: 'ownerId' });
+Item.hasMany(Rental, { as: "rentals", foreignKey: "itemId" });
+Rental.belongsTo(Item, { as: "item", foreignKey: "itemId" });
+Rental.belongsTo(User, { as: "renter", foreignKey: "renterId" });
+Rental.belongsTo(User, { as: "owner", foreignKey: "ownerId" });

-User.hasMany(Message, { as: 'sentMessages', foreignKey: 'senderId' });
-User.hasMany(Message, { as: 'receivedMessages', foreignKey: 'receiverId' });
-Message.belongsTo(User, { as: 'sender', foreignKey: 'senderId' });
-Message.belongsTo(User, { as: 'receiver', foreignKey: 'receiverId' });
-Message.hasMany(Message, { as: 'replies', foreignKey: 'parentMessageId' });
-Message.belongsTo(Message, { as: 'parentMessage', foreignKey: 'parentMessageId' });
+User.hasMany(Message, { as: "sentMessages", foreignKey: "senderId" });
+User.hasMany(Message, { as: "receivedMessages", foreignKey: "receiverId" });
+Message.belongsTo(User, { as: "sender", foreignKey: "senderId" });
+Message.belongsTo(User, { as: "receiver", foreignKey: "receiverId" });
+Message.hasMany(Message, { as: "replies", foreignKey: "parentMessageId" });
+Message.belongsTo(Message, {
+  as: "parentMessage",
+  foreignKey: "parentMessageId",
+});

-User.hasMany(ItemRequest, { as: 'itemRequests', foreignKey: 'requesterId' });
-ItemRequest.belongsTo(User, { as: 'requester', foreignKey: 'requesterId' });
+User.hasMany(ItemRequest, { as: "itemRequests", foreignKey: "requesterId" });
+ItemRequest.belongsTo(User, { as: "requester", foreignKey: "requesterId" });

-User.hasMany(ItemRequestResponse, { as: 'itemRequestResponses', foreignKey: 'responderId' });
-ItemRequest.hasMany(ItemRequestResponse, { as: 'responses', foreignKey: 'itemRequestId' });
-ItemRequestResponse.belongsTo(User, { as: 'responder', foreignKey: 'responderId' });
-ItemRequestResponse.belongsTo(ItemRequest, { as: 'itemRequest', foreignKey: 'itemRequestId' });
-ItemRequestResponse.belongsTo(Item, { as: 'existingItem', foreignKey: 'existingItemId' });
+User.hasMany(ItemRequestResponse, {
+  as: "itemRequestResponses",
+  foreignKey: "responderId",
+});
+ItemRequest.hasMany(ItemRequestResponse, {
+  as: "responses",
+  foreignKey: "itemRequestId",
+});
+ItemRequestResponse.belongsTo(User, {
+  as: "responder",
+  foreignKey: "responderId",
+});
+ItemRequestResponse.belongsTo(ItemRequest, {
+  as: "itemRequest",
+  foreignKey: "itemRequestId",
+});
+ItemRequestResponse.belongsTo(Item, {
+  as: "existingItem",
+  foreignKey: "existingItemId",
+});

-User.hasMany(UserAddress, { as: 'addresses', foreignKey: 'userId' });
-UserAddress.belongsTo(User, { as: 'user', foreignKey: 'userId' });
+User.hasMany(UserAddress, { as: "addresses", foreignKey: "userId" });
+UserAddress.belongsTo(User, { as: "user", foreignKey: "userId" });
+
+// ConditionCheck associations
+Rental.hasMany(ConditionCheck, {
+  as: "conditionChecks",
+  foreignKey: "rentalId",
+});
+ConditionCheck.belongsTo(Rental, { as: "rental", foreignKey: "rentalId" });
+User.hasMany(ConditionCheck, {
+  as: "conditionChecks",
+  foreignKey: "submittedBy",
+});
+ConditionCheck.belongsTo(User, {
+  as: "submittedByUser",
+  foreignKey: "submittedBy",
+});

 module.exports = {
  sequelize,
@@ -45,5 +79,6 @@ module.exports = {
  Message,
  ItemRequest,
  ItemRequestResponse,
-  UserAddress
+  UserAddress,
+  ConditionCheck,
 };
--- a/backend/package-lock.json
+++ b/backend/package-lock.json
--- a/backend/package.json
+++ b/backend/package.json
@@ -21,6 +21,7 @@
  "author": "",
  "license": "ISC",
  "dependencies": {
+    "@aws-sdk/client-ses": "^3.896.0",
    "@googlemaps/google-maps-services-js": "^3.4.2",
    "bcryptjs": "^3.0.2",
    "body-parser": "^2.2.0",
--- a/backend/routes/conditionChecks.js
+++ b/backend/routes/conditionChecks.js
@@ -0,0 +1,165 @@
+const express = require("express");
+const multer = require("multer");
+const { authenticateToken } = require("../middleware/auth");
+const ConditionCheckService = require("../services/conditionCheckService");
+const logger = require("../utils/logger");
+
+const router = express.Router();
+
+// Configure multer for photo uploads
+const upload = multer({
+  dest: "uploads/condition-checks/",
+  limits: {
+    fileSize: 10 * 1024 * 1024, // 10MB limit
+    files: 20, // Maximum 20 files
+  },
+  fileFilter: (req, file, cb) => {
+    // Accept only image files
+    if (file.mimetype.startsWith("image/")) {
+      cb(null, true);
+    } else {
+      cb(new Error("Only image files are allowed"), false);
+    }
+  },
+});
+
+// Submit a condition check
+router.post(
+  "/:rentalId",
+  authenticateToken,
+  upload.array("photos"),
+  async (req, res) => {
+    try {
+      const { rentalId } = req.params;
+      const { checkType, notes } = req.body;
+      const userId = req.user.id;
+
+      // Get uploaded file paths
+      const photos = req.files ? req.files.map((file) => file.path) : [];
+
+      // Extract metadata from request
+      const metadata = {
+        userAgent: req.get("User-Agent"),
+        ipAddress: req.ip,
+        deviceType: req.get("X-Device-Type") || "web",
+      };
+
+      const conditionCheck = await ConditionCheckService.submitConditionCheck(
+        rentalId,
+        checkType,
+        userId,
+        photos,
+        notes,
+        metadata
+      );
+
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Condition check submitted", {
+        rentalId,
+        checkType,
+        userId,
+        photoCount: photos.length,
+      });
+
+      res.status(201).json({
+        success: true,
+        conditionCheck,
+      });
+    } catch (error) {
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Error submitting condition check", {
+        error: error.message,
+        rentalId: req.params.rentalId,
+        userId: req.user?.id,
+      });
+
+      res.status(400).json({
+        success: false,
+        error: error.message,
+      });
+    }
+  }
+);
+
+// Get condition checks for a rental
+router.get("/:rentalId", authenticateToken, async (req, res) => {
+  try {
+    const { rentalId } = req.params;
+
+    const conditionChecks = await ConditionCheckService.getConditionChecks(
+      rentalId
+    );
+
+    res.json({
+      success: true,
+      conditionChecks,
+    });
+  } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error fetching condition checks", {
+      error: error.message,
+      rentalId: req.params.rentalId,
+    });
+
+    res.status(500).json({
+      success: false,
+      error: "Failed to fetch condition checks",
+    });
+  }
+});
+
+// Get condition check timeline for a rental
+router.get("/:rentalId/timeline", authenticateToken, async (req, res) => {
+  try {
+    const { rentalId } = req.params;
+
+    const timeline = await ConditionCheckService.getConditionCheckTimeline(
+      rentalId
+    );
+
+    res.json({
+      success: true,
+      timeline,
+    });
+  } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error fetching condition check timeline", {
+      error: error.message,
+      rentalId: req.params.rentalId,
+    });
+
+    res.status(500).json({
+      success: false,
+      error: error.message,
+    });
+  }
+});
+
+// Get available condition checks for current user
+router.get("/", authenticateToken, async (req, res) => {
+  try {
+    const userId = req.user.id;
+
+    const availableChecks = await ConditionCheckService.getAvailableChecks(
+      userId
+    );
+
+    res.json({
+      success: true,
+      availableChecks,
+    });
+  } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error fetching available checks", {
+      error: error.message,
+      userId: req.user?.id,
+    });
+
+    res.status(500).json({
+      success: false,
+      error: "Failed to fetch available checks",
+    });
+  }
+});
+
+module.exports = router;
--- a/backend/routes/rentals.js
+++ b/backend/routes/rentals.js
@@ -4,6 +4,9 @@ const { Rental, Item, User } = require("../models"); // Import from models/index
 const { authenticateToken } = require("../middleware/auth");
 const FeeCalculator = require("../utils/feeCalculator");
 const RefundService = require("../services/refundService");
+const LateReturnService = require("../services/lateReturnService");
+const DamageAssessmentService = require("../services/damageAssessmentService");
+const emailService = require("../services/emailService");
 const logger = require("../utils/logger");
 const router = express.Router();

@@ -72,7 +75,7 @@ router.get("/my-rentals", authenticateToken, async (req, res) => {
    reqLogger.error("Error in my-rentals route", {
      error: error.message,
      stack: error.stack,
-      userId: req.user.id
+      userId: req.user.id,
    });
    res.status(500).json({ error: "Failed to fetch rentals" });
  }
@@ -100,7 +103,7 @@ router.get("/my-listings", authenticateToken, async (req, res) => {
    reqLogger.error("Error in my-listings route", {
      error: error.message,
      stack: error.stack,
-      userId: req.user.id
+      userId: req.user.id,
    });
    res.status(500).json({ error: "Failed to fetch listings" });
  }
@@ -131,7 +134,9 @@ router.get("/:id", authenticateToken, async (req, res) => {

    // Check if user is authorized to view this rental
    if (rental.ownerId !== req.user.id && rental.renterId !== req.user.id) {
-      return res.status(403).json({ error: "Unauthorized to view this rental" });
+      return res
+        .status(403)
+        .json({ error: "Unauthorized to view this rental" });
    }

    res.json(rental);
@@ -141,7 +146,7 @@ router.get("/:id", authenticateToken, async (req, res) => {
      error: error.message,
      stack: error.stack,
      rentalId: req.params.id,
-      userId: req.user.id
+      userId: req.user.id,
    });
    res.status(500).json({ error: "Failed to fetch rental" });
  }
@@ -235,7 +240,9 @@ router.post("/", authenticateToken, async (req, res) => {

    // Validate that payment method was provided for paid rentals
    if (totalAmount > 0 && !stripePaymentMethodId) {
-      return res.status(400).json({ error: "Payment method is required for paid rentals" });
+      return res
+        .status(400)
+        .json({ error: "Payment method is required for paid rentals" });
    }

    const rentalData = {
@@ -313,7 +320,9 @@ router.put("/:id/status", authenticateToken, async (req, res) => {
    }

    if (rental.ownerId !== req.user.id && rental.renterId !== req.user.id) {
-      return res.status(403).json({ error: "Unauthorized to update this rental" });
+      return res
+        .status(403)
+        .json({ error: "Unauthorized to update this rental" });
    }

    // If owner is approving a pending rental, handle payment for paid rentals
@@ -336,9 +345,9 @@ router.put("/:id/status", authenticateToken, async (req, res) => {

          // Check if renter has a stripe customer ID
          if (!rental.renter.stripeCustomerId) {
-          return res
-            .status(400)
-            .json({ error: "Renter does not have a Stripe customer account" });
+            return res.status(400).json({
+              error: "Renter does not have a Stripe customer account",
+            });
          }

          // Create payment intent and charge the stored payment method
@@ -377,6 +386,9 @@ router.put("/:id/status", authenticateToken, async (req, res) => {
            ],
          });

+          // Send confirmation emails
+          await emailService.sendRentalConfirmationEmails(updatedRental);
+
          res.json(updatedRental);
          return;
        } catch (paymentError) {
@@ -385,7 +397,7 @@ router.put("/:id/status", authenticateToken, async (req, res) => {
            error: paymentError.message,
            stack: paymentError.stack,
            rentalId: req.params.id,
-          userId: req.user.id
+            userId: req.user.id,
          });
          // Keep rental as pending, but inform of payment failure
          return res.status(400).json({
@@ -396,7 +408,7 @@ router.put("/:id/status", authenticateToken, async (req, res) => {
      } else {
        // For free rentals, just update status directly
        await rental.update({
-          status: "confirmed"
+          status: "confirmed",
        });

        const updatedRental = await Rental.findByPk(rental.id, {
@@ -415,6 +427,9 @@ router.put("/:id/status", authenticateToken, async (req, res) => {
          ],
        });

+        // Send confirmation emails
+        await emailService.sendRentalConfirmationEmails(updatedRental);
+
        res.json(updatedRental);
        return;
      }
@@ -601,7 +616,7 @@ router.post("/calculate-fees", authenticateToken, async (req, res) => {
      userId: req.user.id,
      startDate: req.query.startDate,
      endDate: req.query.endDate,
-      itemId: req.query.itemId
+      itemId: req.query.itemId,
    });
    res.status(500).json({ error: "Failed to calculate fees" });
  }
@@ -634,7 +649,7 @@ router.get("/earnings/status", authenticateToken, async (req, res) => {
    reqLogger.error("Error getting earnings status", {
      error: error.message,
      stack: error.stack,
-      userId: req.user.id
+      userId: req.user.id,
    });
    res.status(500).json({ error: error.message });
  }
@@ -654,7 +669,47 @@ router.get("/:id/refund-preview", authenticateToken, async (req, res) => {
      error: error.message,
      stack: error.stack,
      rentalId: req.params.id,
-      userId: req.user.id
+      userId: req.user.id,
+    });
+    res.status(400).json({ error: error.message });
+  }
+});
+
+// Get late fee preview
+router.get("/:id/late-fee-preview", authenticateToken, async (req, res) => {
+  try {
+    const { actualReturnDateTime } = req.query;
+
+    if (!actualReturnDateTime) {
+      return res.status(400).json({ error: "actualReturnDateTime is required" });
+    }
+
+    const rental = await Rental.findByPk(req.params.id, {
+      include: [{ model: Item, as: "item" }],
+    });
+
+    if (!rental) {
+      return res.status(404).json({ error: "Rental not found" });
+    }
+
+    // Check authorization
+    if (rental.ownerId !== req.user.id && rental.renterId !== req.user.id) {
+      return res.status(403).json({ error: "Unauthorized" });
+    }
+
+    const lateCalculation = LateReturnService.calculateLateFee(
+      rental,
+      actualReturnDateTime
+    );
+
+    res.json(lateCalculation);
+  } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error getting late fee preview", {
+      error: error.message,
+      stack: error.stack,
+      rentalId: req.params.id,
+      userId: req.user.id,
    });
    res.status(400).json({ error: error.message });
  }
@@ -698,10 +753,174 @@ router.post("/:id/cancel", authenticateToken, async (req, res) => {
      error: error.message,
      stack: error.stack,
      rentalId: req.params.id,
-      userId: req.user.id
+      userId: req.user.id,
    });
    res.status(400).json({ error: error.message });
  }
 });

+// Mark item return status (owner only)
+router.post("/:id/mark-return", authenticateToken, async (req, res) => {
+  try {
+    const { status, actualReturnDateTime, notes, statusOptions } = req.body;
+    const rentalId = req.params.id;
+    const userId = req.user.id;
+
+    const rental = await Rental.findByPk(rentalId, {
+      include: [{ model: Item, as: "item" }],
+    });
+
+    if (!rental) {
+      return res.status(404).json({ error: "Rental not found" });
+    }
+
+    if (rental.ownerId !== userId) {
+      return res
+        .status(403)
+        .json({ error: "Only the item owner can mark return status" });
+    }
+
+    if (!["confirmed", "active"].includes(rental.status)) {
+      return res.status(400).json({
+        error: "Can only mark return status for confirmed or active rentals",
+      });
+    }
+
+    let updatedRental;
+    let additionalInfo = {};
+
+    switch (status) {
+      case "returned":
+        // Item returned on time
+        updatedRental = await rental.update({
+          status: "completed",
+          actualReturnDateTime: actualReturnDateTime || rental.endDateTime,
+          notes: notes || null,
+        });
+        break;
+
+      case "damaged":
+        // Item returned damaged
+        const damageUpdates = {
+          status: "damaged",
+          actualReturnDateTime: actualReturnDateTime || rental.endDateTime,
+          notes: notes || null,
+        };
+
+        // Check if ALSO returned late
+        if (statusOptions?.returned_late && actualReturnDateTime) {
+          const lateReturnDamaged = await LateReturnService.processLateReturn(
+            rentalId,
+            actualReturnDateTime,
+            notes
+          );
+          damageUpdates.status = "returned_late_and_damaged";
+          damageUpdates.lateFees = lateReturnDamaged.lateCalculation.lateFee;
+          damageUpdates.actualReturnDateTime =
+            lateReturnDamaged.rental.actualReturnDateTime;
+          additionalInfo.lateCalculation = lateReturnDamaged.lateCalculation;
+        }
+
+        updatedRental = await rental.update(damageUpdates);
+        break;
+
+      case "returned_late":
+        // Item returned late - calculate late fees
+        if (!actualReturnDateTime) {
+          return res.status(400).json({
+            error: "Actual return date/time is required for late returns",
+          });
+        }
+
+        const lateReturn = await LateReturnService.processLateReturn(
+          rentalId,
+          actualReturnDateTime,
+          notes
+        );
+
+        updatedRental = lateReturn.rental;
+        additionalInfo.lateCalculation = lateReturn.lateCalculation;
+        break;
+
+      case "lost":
+        // Item reported as lost
+        updatedRental = await rental.update({
+          status: "lost",
+          itemLostReportedAt: new Date(),
+          notes: notes || null,
+        });
+
+        // Send notification to customer service
+        await emailService.sendLostItemToCustomerService(updatedRental);
+        break;
+
+      default:
+        return res.status(400).json({
+          error:
+            "Invalid status. Use 'returned', 'returned_late', 'damaged', or 'lost'",
+        });
+    }
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Return status marked", {
+      rentalId,
+      status,
+      ownerId: userId,
+      lateFee: updatedRental.lateFees || 0,
+    });
+
+    res.json({
+      success: true,
+      rental: updatedRental,
+      ...additionalInfo,
+    });
+  } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error marking return status", {
+      error: error.message,
+      rentalId: req.params.id,
+      userId: req.user.id,
+    });
+
+    res.status(400).json({ error: error.message });
+  }
+});
+
+// Report item as damaged (owner only)
+router.post("/:id/report-damage", authenticateToken, async (req, res) => {
+  try {
+    const rentalId = req.params.id;
+    const userId = req.user.id;
+    const damageInfo = req.body;
+
+    const result = await DamageAssessmentService.processDamageAssessment(
+      rentalId,
+      damageInfo,
+      userId
+    );
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Damage reported", {
+      rentalId,
+      ownerId: userId,
+      damageFee: result.damageAssessment.feeCalculation.amount,
+      lateFee: result.lateCalculation?.lateFee || 0,
+    });
+
+    res.json({
+      success: true,
+      ...result,
+    });
+  } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error reporting damage", {
+      error: error.message,
+      rentalId: req.params.id,
+      userId: req.user.id,
+    });
+
+    res.status(400).json({ error: error.message });
+  }
+});
+
 module.exports = router;
--- a/backend/server.js
+++ b/backend/server.js
@@ -23,8 +23,11 @@ const messageRoutes = require("./routes/messages");
 const itemRequestRoutes = require("./routes/itemRequests");
 const stripeRoutes = require("./routes/stripe");
 const mapsRoutes = require("./routes/maps");
+const conditionCheckRoutes = require("./routes/conditionChecks");

 const PayoutProcessor = require("./jobs/payoutProcessor");
+const RentalStatusJob = require("./jobs/rentalStatusJob");
+const ConditionCheckReminderJob = require("./jobs/conditionCheckReminder");

 const app = express();

@@ -65,7 +68,7 @@ app.use(
 app.use(cookieParser);

 // HTTP request logging
-app.use(morgan('combined', { stream: logger.stream }));
+app.use(morgan("combined", { stream: logger.stream }));

 // API request/response logging
 app.use("/api/", apiLogger);
@@ -111,6 +114,7 @@ app.use("/api/messages", messageRoutes);
 app.use("/api/item-requests", itemRequestRoutes);
 app.use("/api/stripe", stripeRoutes);
 app.use("/api/maps", mapsRoutes);
+app.use("/api/condition-checks", conditionCheckRoutes);

 app.get("/", (req, res) => {
  res.json({ message: "CommunityRentals.App API is running!" });
@@ -131,10 +135,24 @@ sequelize
    const payoutJobs = PayoutProcessor.startScheduledPayouts();
    logger.info("Payout processor started");

+    // Start the rental status job
+    const rentalStatusJobs = RentalStatusJob.startScheduledStatusUpdates();
+    logger.info("Rental status job started");
+
+    // Start the condition check reminder job
+    const conditionCheckJobs = ConditionCheckReminderJob.startScheduledReminders();
+    logger.info("Condition check reminder job started");
+
    app.listen(PORT, () => {
-      logger.info(`Server is running on port ${PORT}`, { port: PORT, environment: env });
+      logger.info(`Server is running on port ${PORT}`, {
+        port: PORT,
+        environment: env,
+      });
    });
  })
  .catch((err) => {
-    logger.error("Unable to sync database", { error: err.message, stack: err.stack });
+    logger.error("Unable to sync database", {
+      error: err.message,
+      stack: err.stack,
+    });
  });
--- a/backend/services/conditionCheckService.js
+++ b/backend/services/conditionCheckService.js
@@ -0,0 +1,363 @@
+const { ConditionCheck, Rental, User } = require("../models");
+const { Op } = require("sequelize");
+
+class ConditionCheckService {
+  /**
+   * Validate if a condition check can be submitted
+   * @param {string} rentalId - Rental ID
+   * @param {string} checkType - Type of check (pre_rental_owner, rental_start_renter, etc.)
+   * @param {string} userId - User attempting to submit
+   * @returns {Object} - { canSubmit, reason, timeWindow }
+   */
+  static async validateConditionCheck(rentalId, checkType, userId) {
+    const rental = await Rental.findByPk(rentalId);
+
+    if (!rental) {
+      return { canSubmit: false, reason: "Rental not found" };
+    }
+
+    // Check user permissions
+    const isOwner = rental.ownerId === userId;
+    const isRenter = rental.renterId === userId;
+
+    if (checkType.includes("owner") && !isOwner) {
+      return {
+        canSubmit: false,
+        reason: "Only the item owner can submit owner condition checks",
+      };
+    }
+
+    if (checkType.includes("renter") && !isRenter) {
+      return {
+        canSubmit: false,
+        reason: "Only the renter can submit renter condition checks",
+      };
+    }
+
+    // Check if already submitted
+    const existingCheck = await ConditionCheck.findOne({
+      where: { rentalId, checkType },
+    });
+
+    if (existingCheck) {
+      return {
+        canSubmit: false,
+        reason: "Condition check already submitted for this type",
+      };
+    }
+
+    // Check time windows (24 hour windows)
+    const now = new Date();
+    const startDate = new Date(rental.startDateTime);
+    const endDate = new Date(rental.endDateTime);
+    const twentyFourHours = 24 * 60 * 60 * 1000;
+
+    let timeWindow = {};
+    let canSubmit = false;
+
+    switch (checkType) {
+      case "pre_rental_owner":
+        // 24 hours before rental starts
+        timeWindow.start = new Date(startDate.getTime() - twentyFourHours);
+        timeWindow.end = startDate;
+        canSubmit = now >= timeWindow.start && now <= timeWindow.end;
+        break;
+
+      case "rental_start_renter":
+        // 24 hours after rental starts
+        timeWindow.start = startDate;
+        timeWindow.end = new Date(startDate.getTime() + twentyFourHours);
+        canSubmit =
+          now >= timeWindow.start &&
+          now <= timeWindow.end &&
+          rental.status === "active";
+        break;
+
+      case "rental_end_renter":
+        // 24 hours before rental ends
+        timeWindow.start = new Date(endDate.getTime() - twentyFourHours);
+        timeWindow.end = endDate;
+        canSubmit =
+          now >= timeWindow.start &&
+          now <= timeWindow.end &&
+          rental.status === "active";
+        break;
+
+      case "post_rental_owner":
+        // Can be submitted anytime (integrated into return flow)
+        timeWindow.start = endDate;
+        timeWindow.end = null; // No time limit
+        canSubmit = true; // Always allowed when owner marks return
+        break;
+
+      default:
+        return { canSubmit: false, reason: "Invalid check type" };
+    }
+
+    if (!canSubmit) {
+      const isBeforeWindow = now < timeWindow.start;
+      const isAfterWindow = now > timeWindow.end;
+
+      let reason = "Outside of allowed time window";
+      if (isBeforeWindow) {
+        reason = `Too early. Check can be submitted starting ${timeWindow.start.toLocaleString()}`;
+      } else if (isAfterWindow) {
+        reason = `Pre-Rental Condition can only be submitted before start of rental period`;
+      }
+
+      return { canSubmit: false, reason, timeWindow };
+    }
+
+    return { canSubmit: true, timeWindow };
+  }
+
+  /**
+   * Submit a condition check with photos
+   * @param {string} rentalId - Rental ID
+   * @param {string} checkType - Type of check
+   * @param {string} userId - User submitting the check
+   * @param {Array} photos - Array of photo URLs
+   * @param {string} notes - Optional notes
+   * @param {Object} metadata - Additional metadata (device info, location, etc.)
+   * @returns {Object} - Created condition check
+   */
+  static async submitConditionCheck(
+    rentalId,
+    checkType,
+    userId,
+    photos = [],
+    notes = null,
+    metadata = {}
+  ) {
+    // Validate the check
+    const validation = await this.validateConditionCheck(
+      rentalId,
+      checkType,
+      userId
+    );
+
+    if (!validation.canSubmit) {
+      throw new Error(validation.reason);
+    }
+
+    // Validate photos (basic validation)
+    if (photos.length > 20) {
+      throw new Error("Maximum 20 photos allowed per condition check");
+    }
+
+    // Add timestamp and user agent to metadata
+    const enrichedMetadata = {
+      ...metadata,
+      submittedAt: new Date().toISOString(),
+      userAgent: metadata.userAgent || "Unknown",
+      ipAddress: metadata.ipAddress || "Unknown",
+      deviceType: metadata.deviceType || "Unknown",
+    };
+
+    const conditionCheck = await ConditionCheck.create({
+      rentalId,
+      checkType,
+      submittedBy: userId,
+      photos,
+      notes,
+      metadata: enrichedMetadata,
+    });
+
+    return conditionCheck;
+  }
+
+  /**
+   * Get all condition checks for a rental
+   * @param {string} rentalId - Rental ID
+   * @returns {Array} - Array of condition checks with user info
+   */
+  static async getConditionChecks(rentalId) {
+    const checks = await ConditionCheck.findAll({
+      where: { rentalId },
+      include: [
+        {
+          model: User,
+          as: "submittedByUser",
+          attributes: ["id", "username", "firstName", "lastName"],
+        },
+      ],
+      order: [["submittedAt", "ASC"]],
+    });
+
+    return checks;
+  }
+
+  /**
+   * Get condition check timeline for a rental
+   * @param {string} rentalId - Rental ID
+   * @returns {Object} - Timeline showing what checks are available/completed
+   */
+  static async getConditionCheckTimeline(rentalId) {
+    const rental = await Rental.findByPk(rentalId);
+    if (!rental) {
+      throw new Error("Rental not found");
+    }
+
+    const existingChecks = await ConditionCheck.findAll({
+      where: { rentalId },
+      include: [
+        {
+          model: User,
+          as: "submittedByUser",
+          attributes: ["id", "username", "firstName", "lastName"],
+        },
+      ],
+    });
+
+    const checkTypes = [
+      "pre_rental_owner",
+      "rental_start_renter",
+      "rental_end_renter",
+      "post_rental_owner",
+    ];
+
+    const timeline = {};
+
+    for (const checkType of checkTypes) {
+      const existingCheck = existingChecks.find(
+        (check) => check.checkType === checkType
+      );
+
+      if (existingCheck) {
+        timeline[checkType] = {
+          status: "completed",
+          submittedAt: existingCheck.submittedAt,
+          submittedBy: existingCheck.submittedBy,
+          photoCount: existingCheck.photos.length,
+          hasNotes: !!existingCheck.notes,
+        };
+      } else {
+        // Calculate if this check type is available
+        const now = new Date();
+        const startDate = new Date(rental.startDateTime);
+        const endDate = new Date(rental.endDateTime);
+        const twentyFourHours = 24 * 60 * 60 * 1000;
+
+        let timeWindow = {};
+        let status = "not_available";
+
+        switch (checkType) {
+          case "pre_rental_owner":
+            timeWindow.start = new Date(startDate.getTime() - twentyFourHours);
+            timeWindow.end = startDate;
+            break;
+          case "rental_start_renter":
+            timeWindow.start = startDate;
+            timeWindow.end = new Date(startDate.getTime() + twentyFourHours);
+            break;
+          case "rental_end_renter":
+            timeWindow.start = new Date(endDate.getTime() - twentyFourHours);
+            timeWindow.end = endDate;
+            break;
+          case "post_rental_owner":
+            timeWindow.start = endDate;
+            timeWindow.end = new Date(endDate.getTime() + twentyFourHours);
+            break;
+        }
+
+        if (now >= timeWindow.start && now <= timeWindow.end) {
+          status = "available";
+        } else if (now < timeWindow.start) {
+          status = "pending";
+        } else {
+          status = "expired";
+        }
+
+        timeline[checkType] = {
+          status,
+          timeWindow,
+          availableFrom: timeWindow.start,
+          availableUntil: timeWindow.end,
+        };
+      }
+    }
+
+    return {
+      rental: {
+        id: rental.id,
+        startDateTime: rental.startDateTime,
+        endDateTime: rental.endDateTime,
+        status: rental.status,
+      },
+      timeline,
+    };
+  }
+
+  /**
+   * Get available condition checks for a user
+   * @param {string} userId - User ID
+   * @returns {Array} - Array of available condition checks
+   */
+  static async getAvailableChecks(userId) {
+    const now = new Date();
+    const twentyFourHours = 24 * 60 * 60 * 1000;
+
+    // Find rentals where user is owner or renter
+    const rentals = await Rental.findAll({
+      where: {
+        [Op.or]: [{ ownerId: userId }, { renterId: userId }],
+        status: {
+          [Op.in]: ["confirmed", "active", "completed"],
+        },
+      },
+    });
+
+    const availableChecks = [];
+
+    for (const rental of rentals) {
+      const isOwner = rental.ownerId === userId;
+      const isRenter = rental.renterId === userId;
+      const startDate = new Date(rental.startDateTime);
+      const endDate = new Date(rental.endDateTime);
+
+      // Check each type of condition check
+      const checkTypes = [];
+
+      if (isOwner) {
+        // Only include pre_rental_owner; post_rental is now part of return flow
+        checkTypes.push("pre_rental_owner");
+      }
+      if (isRenter) {
+        checkTypes.push("rental_start_renter", "rental_end_renter");
+      }
+
+      for (const checkType of checkTypes) {
+        // Check if already submitted
+        const existing = await ConditionCheck.findOne({
+          where: { rentalId: rental.id, checkType },
+        });
+
+        if (!existing) {
+          const validation = await this.validateConditionCheck(
+            rental.id,
+            checkType,
+            userId
+          );
+
+          if (validation.canSubmit) {
+            availableChecks.push({
+              rentalId: rental.id,
+              checkType,
+              rental: {
+                id: rental.id,
+                itemId: rental.itemId,
+                startDateTime: rental.startDateTime,
+                endDateTime: rental.endDateTime,
+              },
+              timeWindow: validation.timeWindow,
+            });
+          }
+        }
+      }
+    }
+
+    return availableChecks;
+  }
+}
+
+module.exports = ConditionCheckService;
--- a/backend/services/damageAssessmentService.js
+++ b/backend/services/damageAssessmentService.js
@@ -0,0 +1,138 @@
+const { Rental, Item, ConditionCheck } = require("../models");
+const LateReturnService = require("./lateReturnService");
+const emailService = require("./emailService");
+
+class DamageAssessmentService {
+  /**
+   * Process damage assessment and calculate fees
+   * @param {string} rentalId - Rental ID
+   * @param {Object} damageInfo - Damage assessment information
+   * @param {string} userId - Owner reporting the damage
+   * @returns {Object} - Updated rental with damage fees
+   */
+  static async processDamageAssessment(rentalId, damageInfo, userId) {
+    const {
+      description,
+      canBeFixed,
+      repairCost,
+      needsReplacement,
+      replacementCost,
+      proofOfOwnership,
+      actualReturnDateTime,
+      photos = [],
+    } = damageInfo;
+
+    const rental = await Rental.findByPk(rentalId, {
+      include: [{ model: Item, as: "item" }],
+    });
+
+    if (!rental) {
+      throw new Error("Rental not found");
+    }
+
+    if (rental.ownerId !== userId) {
+      throw new Error("Only the item owner can report damage");
+    }
+
+    if (rental.status !== "active") {
+      throw new Error("Can only assess damage for active rentals");
+    }
+
+    // Validate required fields
+    if (!description || description.trim().length === 0) {
+      throw new Error("Damage description is required");
+    }
+
+    if (canBeFixed && (!repairCost || repairCost <= 0)) {
+      throw new Error("Repair cost is required when item can be fixed");
+    }
+
+    if (needsReplacement && (!replacementCost || replacementCost <= 0)) {
+      throw new Error(
+        "Replacement cost is required when item needs replacement"
+      );
+    }
+
+    // Calculate damage fees
+    let damageFees = 0;
+    let feeCalculation = {};
+
+    if (needsReplacement) {
+      // Full replacement cost
+      damageFees = parseFloat(replacementCost);
+      feeCalculation = {
+        type: "replacement",
+        amount: damageFees,
+        originalCost: replacementCost,
+        depreciation: 0,
+      };
+    } else if (canBeFixed && repairCost > 0) {
+      // Repair cost
+      damageFees = parseFloat(repairCost);
+      feeCalculation = {
+        type: "repair",
+        amount: damageFees,
+        repairCost: repairCost,
+      };
+    }
+
+    // Process late return if applicable
+    let lateFees = 0;
+    let lateCalculation = null;
+
+    if (actualReturnDateTime) {
+      const lateReturn = await LateReturnService.processLateReturn(
+        rentalId,
+        actualReturnDateTime,
+        `Item returned damaged: ${description}`
+      );
+      lateFees = lateReturn.lateCalculation.lateFee;
+      lateCalculation = lateReturn.lateCalculation;
+    }
+
+    // Create damage assessment record as metadata
+    const damageAssessment = {
+      description,
+      canBeFixed,
+      repairCost: canBeFixed ? parseFloat(repairCost) : null,
+      needsReplacement,
+      replacementCost: needsReplacement ? parseFloat(replacementCost) : null,
+      proofOfOwnership: proofOfOwnership || [],
+      photos,
+      assessedAt: new Date(),
+      assessedBy: userId,
+      feeCalculation,
+    };
+
+    // Update rental
+    const updates = {
+      status: "damaged",
+      damageFees: damageFees,
+      damageAssessment: damageAssessment,
+    };
+
+    // Add late fees if applicable
+    if (lateFees > 0) {
+      updates.lateFees = lateFees;
+      updates.actualReturnDateTime = new Date(actualReturnDateTime);
+    }
+
+    const updatedRental = await rental.update(updates);
+
+    // Send damage report to customer service for review
+    await emailService.sendDamageReportToCustomerService(
+      updatedRental,
+      damageAssessment,
+      lateCalculation
+    );
+
+    return {
+      rental: updatedRental,
+      damageAssessment,
+      lateCalculation,
+      totalAdditionalFees: damageFees + lateFees,
+    };
+  }
+}
+
+module.exports = DamageAssessmentService;
--- a/backend/services/emailService.js
+++ b/backend/services/emailService.js
@@ -0,0 +1,497 @@
+const { SESClient, SendEmailCommand } = require("@aws-sdk/client-ses");
+const fs = require("fs").promises;
+const path = require("path");
+const { getAWSConfig } = require("../config/aws");
+const { User } = require("../models");
+
+class EmailService {
+  constructor() {
+    this.sesClient = null;
+    this.initialized = false;
+    this.templates = new Map();
+  }
+
+  async initialize() {
+    if (this.initialized) return;
+
+    try {
+      // Use centralized AWS configuration with credential profiles
+      const awsConfig = getAWSConfig();
+      this.sesClient = new SESClient(awsConfig);
+
+      await this.loadEmailTemplates();
+      this.initialized = true;
+      console.log("SES Email Service initialized successfully");
+    } catch (error) {
+      console.error("Failed to initialize SES Email Service:", error);
+      throw error;
+    }
+  }
+
+  async loadEmailTemplates() {
+    const templatesDir = path.join(__dirname, "..", "templates", "emails");
+
+    try {
+      const templateFiles = [
+        "conditionCheckReminder.html",
+        "rentalConfirmation.html",
+        "lateReturnCS.html",
+        "damageReportCS.html",
+        "lostItemCS.html",
+      ];
+
+      for (const templateFile of templateFiles) {
+        try {
+          const templatePath = path.join(templatesDir, templateFile);
+          const templateContent = await fs.readFile(templatePath, "utf-8");
+          const templateName = path.basename(templateFile, ".html");
+          this.templates.set(templateName, templateContent);
+        } catch (error) {
+          console.warn(`Template ${templateFile} not found, will use fallback`);
+        }
+      }
+
+      console.log(`Loaded ${this.templates.size} email templates`);
+    } catch (error) {
+      console.warn("Templates directory not found, using fallback templates");
+    }
+  }
+
+  async sendEmail(to, subject, htmlContent, textContent = null) {
+    if (!this.initialized) {
+      await this.initialize();
+    }
+
+    if (!process.env.EMAIL_ENABLED || process.env.EMAIL_ENABLED !== "true") {
+      console.log("Email sending disabled in environment");
+      return { success: true, messageId: "disabled" };
+    }
+
+    const params = {
+      Source: process.env.SES_FROM_EMAIL,
+      Destination: {
+        ToAddresses: Array.isArray(to) ? to : [to],
+      },
+      Message: {
+        Subject: {
+          Data: subject,
+          Charset: "UTF-8",
+        },
+        Body: {
+          Html: {
+            Data: htmlContent,
+            Charset: "UTF-8",
+          },
+        },
+      },
+    };
+
+    if (textContent) {
+      params.Message.Body.Text = {
+        Data: textContent,
+        Charset: "UTF-8",
+      };
+    }
+
+    if (process.env.SES_REPLY_TO_EMAIL) {
+      params.ReplyToAddresses = [process.env.SES_REPLY_TO_EMAIL];
+    }
+
+    try {
+      const command = new SendEmailCommand(params);
+      const result = await this.sesClient.send(command);
+
+      console.log(
+        `Email sent successfully to ${to}, MessageId: ${result.MessageId}`
+      );
+      return { success: true, messageId: result.MessageId };
+    } catch (error) {
+      console.error("Failed to send email:", error);
+      return { success: false, error: error.message };
+    }
+  }
+
+  renderTemplate(templateName, variables = {}) {
+    let template = this.templates.get(templateName);
+
+    if (!template) {
+      template = this.getFallbackTemplate(templateName);
+    }
+
+    let rendered = template;
+
+    Object.keys(variables).forEach((key) => {
+      const regex = new RegExp(`{{${key}}}`, "g");
+      rendered = rendered.replace(regex, variables[key] || "");
+    });
+
+    return rendered;
+  }
+
+  getFallbackTemplate(templateName) {
+    const baseTemplate = `
+      <!DOCTYPE html>
+      <html>
+      <head>
+        <meta charset="utf-8">
+        <meta name="viewport" content="width=device-width, initial-scale=1.0">
+        <title>{{title}}</title>
+        <style>
+          body { font-family: Arial, sans-serif; margin: 0; padding: 20px; background-color: #f5f5f5; }
+          .container { max-width: 600px; margin: 0 auto; background-color: white; padding: 30px; border-radius: 8px; box-shadow: 0 2px 4px rgba(0,0,0,0.1); }
+          .header { text-align: center; border-bottom: 2px solid #e9ecef; padding-bottom: 20px; margin-bottom: 30px; }
+          .logo { font-size: 24px; font-weight: bold; color: #333; }
+          .content { line-height: 1.6; color: #555; }
+          .button { display: inline-block; background-color: #007bff; color: white; padding: 12px 24px; text-decoration: none; border-radius: 4px; margin: 20px 0; }
+          .footer { margin-top: 30px; padding-top: 20px; border-top: 1px solid #e9ecef; text-align: center; font-size: 12px; color: #6c757d; }
+        </style>
+      </head>
+      <body>
+        <div class="container">
+          <div class="header">
+            <div class="logo">RentAll</div>
+          </div>
+          <div class="content">
+            {{content}}
+          </div>
+          <div class="footer">
+            <p>This email was sent from RentAll. If you have any questions, please contact support.</p>
+          </div>
+        </div>
+      </body>
+      </html>
+    `;
+
+    const templates = {
+      conditionCheckReminder: baseTemplate.replace(
+        "{{content}}",
+        `
+        <h2>{{title}}</h2>
+        <p>{{message}}</p>
+        <p><strong>Rental Item:</strong> {{itemName}}</p>
+        <p><strong>Deadline:</strong> {{deadline}}</p>
+        <p>Please complete this condition check as soon as possible to ensure proper documentation.</p>
+      `
+      ),
+
+      rentalConfirmation: baseTemplate.replace(
+        "{{content}}",
+        `
+        <h2>{{title}}</h2>
+        <p>{{message}}</p>
+        <p><strong>Item:</strong> {{itemName}}</p>
+        <p><strong>Rental Period:</strong> {{startDate}} to {{endDate}}</p>
+        <p>Thank you for using RentAll!</p>
+      `
+      ),
+
+      damageClaimNotification: baseTemplate.replace(
+        "{{content}}",
+        `
+        <h2>{{title}}</h2>
+        <p>{{message}}</p>
+        <p><strong>Item:</strong> {{itemName}}</p>
+        <p><strong>Claim Amount:</strong> ${{ claimAmount }}</p>
+        <p><strong>Description:</strong> {{description}}</p>
+        <p>Please review this claim and respond accordingly through your account.</p>
+      `
+      ),
+
+      returnIssueNotification: baseTemplate.replace(
+        "{{content}}",
+        `
+        <h2>{{title}}</h2>
+        <p>{{message}}</p>
+        <p><strong>Item:</strong> {{itemName}}</p>
+        <p><strong>Return Status:</strong> {{returnStatus}}</p>
+        <p>Please check your account for more details and take appropriate action.</p>
+      `
+      ),
+    };
+
+    return (
+      templates[templateName] ||
+      baseTemplate.replace(
+        "{{content}}",
+        `
+      <h2>{{title}}</h2>
+      <p>{{message}}</p>
+    `
+      )
+    );
+  }
+
+  async sendConditionCheckReminder(userEmail, notification, rental) {
+    const variables = {
+      title: notification.title,
+      message: notification.message,
+      itemName: rental?.item?.name || "Unknown Item",
+      deadline: notification.metadata?.deadline
+        ? new Date(notification.metadata.deadline).toLocaleDateString()
+        : "Not specified",
+    };
+
+    const htmlContent = this.renderTemplate(
+      "conditionCheckReminder",
+      variables
+    );
+
+    return await this.sendEmail(
+      userEmail,
+      `RentAll: ${notification.title}`,
+      htmlContent
+    );
+  }
+
+  async sendRentalConfirmation(userEmail, notification, rental) {
+    const variables = {
+      title: notification.title,
+      message: notification.message,
+      itemName: rental?.item?.name || "Unknown Item",
+      startDate: rental?.startDateTime
+        ? new Date(rental.startDateTime).toLocaleDateString()
+        : "Not specified",
+      endDate: rental?.endDateTime
+        ? new Date(rental.endDateTime).toLocaleDateString()
+        : "Not specified",
+    };
+
+    const htmlContent = this.renderTemplate("rentalConfirmation", variables);
+
+    return await this.sendEmail(
+      userEmail,
+      `RentAll: ${notification.title}`,
+      htmlContent
+    );
+  }
+
+  async sendTemplateEmail(toEmail, subject, templateName, variables = {}) {
+    const htmlContent = this.renderTemplate(templateName, variables);
+    return await this.sendEmail(toEmail, subject, htmlContent);
+  }
+
+  async sendLateReturnToCustomerService(rental, lateCalculation) {
+    try {
+      // Get owner and renter details
+      const owner = await User.findByPk(rental.ownerId);
+      const renter = await User.findByPk(rental.renterId);
+
+      if (!owner || !renter) {
+        console.error("Owner or renter not found for late return notification");
+        return;
+      }
+
+      // Format dates
+      const scheduledEnd = new Date(rental.endDateTime).toLocaleString();
+      const actualReturn = new Date(
+        rental.actualReturnDateTime
+      ).toLocaleString();
+
+      // Send email to customer service
+      await this.sendTemplateEmail(
+        process.env.CUSTOMER_SUPPORT_EMAIL,
+        "Late Return Detected - Action Required",
+        "lateReturnCS",
+        {
+          rentalId: rental.id,
+          itemName: rental.item.name,
+          ownerName: owner.name,
+          ownerEmail: owner.email,
+          renterName: renter.name,
+          renterEmail: renter.email,
+          scheduledEnd,
+          actualReturn,
+          hoursLate: lateCalculation.lateHours.toFixed(1),
+          lateFee: lateCalculation.lateFee.toFixed(2),
+        }
+      );
+
+      console.log(
+        `Late return notification sent to customer service for rental ${rental.id}`
+      );
+    } catch (error) {
+      console.error(
+        "Failed to send late return notification to customer service:",
+        error
+      );
+    }
+  }
+
+  async sendDamageReportToCustomerService(
+    rental,
+    damageAssessment,
+    lateCalculation = null
+  ) {
+    try {
+      // Get owner and renter details
+      const owner = await User.findByPk(rental.ownerId);
+      const renter = await User.findByPk(rental.renterId);
+
+      if (!owner || !renter) {
+        console.error(
+          "Owner or renter not found for damage report notification"
+        );
+        return;
+      }
+
+      // Calculate total fees
+      const damageFee = damageAssessment.feeCalculation.amount;
+      const lateFee = lateCalculation?.lateFee || 0;
+      const totalFees = damageFee + lateFee;
+
+      // Determine fee type description
+      let feeTypeDescription = "";
+      if (damageAssessment.feeCalculation.type === "repair") {
+        feeTypeDescription = "Repair Cost";
+      } else if (damageAssessment.feeCalculation.type === "replacement") {
+        feeTypeDescription = "Replacement Cost";
+      } else {
+        feeTypeDescription = "Damage Assessment Fee";
+      }
+
+      // Send email to customer service
+      await this.sendTemplateEmail(
+        process.env.CUSTOMER_SUPPORT_EMAIL,
+        "Damage Report Filed - Action Required",
+        "damageReportCS",
+        {
+          rentalId: rental.id,
+          itemName: rental.item.name,
+          ownerName: `${owner.firstName} ${owner.lastName}`,
+          ownerEmail: owner.email,
+          renterName: `${renter.firstName} ${renter.lastName}`,
+          renterEmail: renter.email,
+          damageDescription: damageAssessment.description,
+          canBeFixed: damageAssessment.canBeFixed ? "Yes" : "No",
+          repairCost: damageAssessment.repairCost
+            ? damageAssessment.repairCost.toFixed(2)
+            : "N/A",
+          needsReplacement: damageAssessment.needsReplacement ? "Yes" : "No",
+          replacementCost: damageAssessment.replacementCost
+            ? damageAssessment.replacementCost.toFixed(2)
+            : "N/A",
+          feeTypeDescription,
+          damageFee: damageFee.toFixed(2),
+          lateFee: lateFee.toFixed(2),
+          totalFees: totalFees.toFixed(2),
+          hasProofOfOwnership:
+            damageAssessment.proofOfOwnership &&
+            damageAssessment.proofOfOwnership.length > 0
+              ? "Yes"
+              : "No",
+        }
+      );
+
+      console.log(
+        `Damage report notification sent to customer service for rental ${rental.id}`
+      );
+    } catch (error) {
+      console.error(
+        "Failed to send damage report notification to customer service:",
+        error
+      );
+    }
+  }
+
+  async sendLostItemToCustomerService(rental) {
+    try {
+      // Get owner and renter details
+      const owner = await User.findByPk(rental.ownerId);
+      const renter = await User.findByPk(rental.renterId);
+
+      if (!owner || !renter) {
+        console.error("Owner or renter not found for lost item notification");
+        return;
+      }
+
+      // Format dates
+      const reportedAt = new Date(rental.itemLostReportedAt).toLocaleString();
+      const scheduledReturnDate = new Date(rental.endDateTime).toLocaleString();
+
+      // Send email to customer service
+      await this.sendTemplateEmail(
+        process.env.CUSTOMER_SUPPORT_EMAIL,
+        "Lost Item Claim Filed - Action Required",
+        "lostItemCS",
+        {
+          rentalId: rental.id,
+          itemName: rental.item.name,
+          ownerName: `${owner.firstName} ${owner.lastName}`,
+          ownerEmail: owner.email,
+          renterName: `${renter.firstName} ${renter.lastName}`,
+          renterEmail: renter.email,
+          reportedAt,
+          scheduledReturnDate,
+          replacementCost: parseFloat(rental.item.replacementCost).toFixed(2),
+        }
+      );
+
+      console.log(
+        `Lost item notification sent to customer service for rental ${rental.id}`
+      );
+    } catch (error) {
+      console.error(
+        "Failed to send lost item notification to customer service:",
+        error
+      );
+    }
+  }
+
+  async sendRentalConfirmationEmails(rental) {
+    try {
+      // Get owner and renter emails
+      const owner = await User.findByPk(rental.ownerId, {
+        attributes: ["email"],
+      });
+      const renter = await User.findByPk(rental.renterId, {
+        attributes: ["email"],
+      });
+
+      // Create notification data for owner
+      const ownerNotification = {
+        type: "rental_confirmed",
+        title: "Rental Confirmed",
+        message: `Your "${rental.item.name}" has been confirmed for rental.`,
+        rentalId: rental.id,
+        userId: rental.ownerId,
+        metadata: { rentalStart: rental.startDateTime },
+      };
+
+      // Create notification data for renter
+      const renterNotification = {
+        type: "rental_confirmed",
+        title: "Rental Confirmed",
+        message: `Your rental of "${rental.item.name}" has been confirmed.`,
+        rentalId: rental.id,
+        userId: rental.renterId,
+        metadata: { rentalStart: rental.startDateTime },
+      };
+
+      // Send email to owner
+      if (owner?.email) {
+        await this.sendRentalConfirmation(
+          owner.email,
+          ownerNotification,
+          rental
+        );
+        console.log(`Rental confirmation email sent to owner: ${owner.email}`);
+      }
+
+      // Send email to renter
+      if (renter?.email) {
+        await this.sendRentalConfirmation(
+          renter.email,
+          renterNotification,
+          rental
+        );
+        console.log(
+          `Rental confirmation email sent to renter: ${renter.email}`
+        );
+      }
+    } catch (error) {
+      console.error("Error sending rental confirmation emails:", error);
+    }
+  }
+}
+
+module.exports = new EmailService();
--- a/backend/services/lateReturnService.js
+++ b/backend/services/lateReturnService.js
@@ -0,0 +1,113 @@
+const { Rental, Item } = require("../models");
+const emailService = require("./emailService");
+
+class LateReturnService {
+  /**
+   * Calculate late fees based on actual return time vs scheduled end time
+   * @param {Object} rental - Rental instance with populated item data
+   * @param {Date} actualReturnDateTime - When the item was actually returned
+   * @returns {Object} - { lateHours, lateFee, isLate }
+   */
+  static calculateLateFee(rental, actualReturnDateTime) {
+    const scheduledEnd = new Date(rental.endDateTime);
+    const actualReturn = new Date(actualReturnDateTime);
+
+    // Calculate hours late
+    const hoursLate = (actualReturn - scheduledEnd) / (1000 * 60 * 60);
+
+    if (hoursLate <= 0) {
+      return {
+        lateHours: 0,
+        lateFee: 0.0,
+        isLate: false,
+      };
+    }
+
+    let lateFee = 0;
+    let pricingType = "daily";
+
+    // Check if item has hourly or daily pricing
+    if (rental.item?.pricePerHour && rental.item.pricePerHour > 0) {
+      // Hourly pricing - charge per hour late
+      lateFee = hoursLate * parseFloat(rental.item.pricePerHour);
+      pricingType = "hourly";
+    } else if (rental.item?.pricePerDay && rental.item.pricePerDay > 0) {
+      // Daily pricing - charge per day late (rounded up)
+      const billableDays = Math.ceil(hoursLate / 24);
+      lateFee = billableDays * parseFloat(rental.item.pricePerDay);
+      pricingType = "daily";
+    } else {
+      // Free borrows: determine pricing type based on rental duration
+      const rentalStart = new Date(rental.startDateTime);
+      const rentalEnd = new Date(rental.endDateTime);
+      const rentalDurationHours = (rentalEnd - rentalStart) / (1000 * 60 * 60);
+
+      if (rentalDurationHours <= 24) {
+        // Hourly rental - charge $10 per hour late
+        lateFee = hoursLate * 10.0;
+        pricingType = "hourly";
+      } else {
+        // Daily rental - charge $10 per day late
+        const billableDays = Math.ceil(hoursLate / 24);
+        lateFee = billableDays * 10.0;
+        pricingType = "daily";
+      }
+    }
+
+    return {
+      lateHours: hoursLate,
+      lateFee: parseFloat(lateFee.toFixed(2)),
+      isLate: true,
+      pricingType,
+    };
+  }
+
+  /**
+   * Process late return and update rental with fees
+   * @param {string} rentalId - Rental ID
+   * @param {Date} actualReturnDateTime - When item was returned
+   * @param {string} notes - Optional notes about the return
+   * @returns {Object} - Updated rental with late fee information
+   */
+  static async processLateReturn(rentalId, actualReturnDateTime, notes = null) {
+    const rental = await Rental.findByPk(rentalId, {
+      include: [{ model: Item, as: "item" }],
+    });
+
+    if (!rental) {
+      throw new Error("Rental not found");
+    }
+
+    if (rental.status !== "active") {
+      throw new Error("Can only process late returns for active rentals");
+    }
+
+    const lateCalculation = this.calculateLateFee(rental, actualReturnDateTime);
+
+    const updates = {
+      actualReturnDateTime: new Date(actualReturnDateTime),
+      status: lateCalculation.isLate ? "returned_late" : "completed",
+    };
+
+    if (notes) {
+      updates.notes = notes;
+    }
+
+    const updatedRental = await rental.update(updates);
+
+    // Send notification to customer service if late return detected
+    if (lateCalculation.isLate && lateCalculation.lateFee > 0) {
+      await emailService.sendLateReturnToCustomerService(
+        updatedRental,
+        lateCalculation
+      );
+    }
+
+    return {
+      rental: updatedRental,
+      lateCalculation,
+    };
+  }
+}
+
+module.exports = LateReturnService;
--- a/backend/services/stripeService.js
+++ b/backend/services/stripeService.js
@@ -162,6 +162,9 @@ class StripeService {
        mode: 'setup',
        ui_mode: 'embedded',
        redirect_on_completion: 'never',
+        setup_intent_data: {
+          usage: 'off_session'
+        },
        metadata: {
          type: 'payment_method_setup',
          ...metadata
--- a/backend/templates/emails/conditionCheckReminder.html
+++ b/backend/templates/emails/conditionCheckReminder.html
@@ -0,0 +1,241 @@
+<!DOCTYPE html>
+<html lang="en">
+<head>
+    <meta charset="utf-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1.0">
+    <meta http-equiv="X-UA-Compatible" content="IE=edge">
+    <title>{{title}}</title>
+    <style>
+        /* Reset styles */
+        body, table, td, p, a, li, blockquote {
+            -webkit-text-size-adjust: 100%;
+            -ms-text-size-adjust: 100%;
+        }
+        table, td {
+            mso-table-lspace: 0pt;
+            mso-table-rspace: 0pt;
+        }
+        img {
+            -ms-interpolation-mode: bicubic;
+        }
+
+        /* Base styles */
+        body {
+            margin: 0;
+            padding: 0;
+            width: 100% !important;
+            min-width: 100%;
+            height: 100%;
+            background-color: #f8f9fa;
+            font-family: -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, Oxygen, Ubuntu, Cantarell, sans-serif;
+            line-height: 1.6;
+            color: #212529;
+        }
+
+        /* Container */
+        .email-container {
+            max-width: 600px;
+            margin: 0 auto;
+            background-color: #ffffff;
+            border-radius: 8px;
+            overflow: hidden;
+            box-shadow: 0 4px 6px rgba(0, 0, 0, 0.1);
+        }
+
+        /* Header */
+        .header {
+            background: linear-gradient(135deg, #667eea 0%, #764ba2 100%);
+            padding: 40px 30px;
+            text-align: center;
+        }
+
+        .logo {
+            font-size: 32px;
+            font-weight: 700;
+            color: #ffffff;
+            text-decoration: none;
+            letter-spacing: -1px;
+        }
+
+        .tagline {
+            color: #e9ecef;
+            font-size: 14px;
+            margin-top: 8px;
+        }
+
+        /* Content */
+        .content {
+            padding: 40px 30px;
+        }
+
+        .content h1 {
+            font-size: 24px;
+            font-weight: 600;
+            margin: 0 0 20px 0;
+            color: #212529;
+        }
+
+        .content h2 {
+            font-size: 20px;
+            font-weight: 600;
+            margin: 30px 0 15px 0;
+            color: #495057;
+        }
+
+        .content p {
+            margin: 0 0 16px 0;
+            color: #6c757d;
+            line-height: 1.6;
+        }
+
+        .content strong {
+            color: #495057;
+        }
+
+        /* Button */
+        .button {
+            display: inline-block;
+            background: linear-gradient(135deg, #667eea 0%, #764ba2 100%);
+            color: #ffffff !important;
+            text-decoration: none;
+            padding: 16px 32px;
+            border-radius: 6px;
+            font-weight: 600;
+            margin: 20px 0;
+            text-align: center;
+            transition: all 0.3s ease;
+        }
+
+        .button:hover {
+            transform: translateY(-2px);
+            box-shadow: 0 4px 12px rgba(102, 126, 234, 0.4);
+        }
+
+        /* Info box */
+        .info-box {
+            background-color: #e3f2fd;
+            border-left: 4px solid #2196f3;
+            padding: 20px;
+            margin: 20px 0;
+            border-radius: 0 6px 6px 0;
+        }
+
+        .info-box p {
+            margin: 0;
+            color: #1565c0;
+        }
+
+        .info-box .icon {
+            font-size: 24px;
+            margin-bottom: 10px;
+        }
+
+        /* Alert box */
+        .alert-box {
+            background-color: #fff3cd;
+            border-left: 4px solid #ffc107;
+            padding: 20px;
+            margin: 20px 0;
+            border-radius: 0 6px 6px 0;
+        }
+
+        .alert-box p {
+            margin: 0;
+            color: #856404;
+        }
+
+        /* Footer */
+        .footer {
+            background-color: #f8f9fa;
+            padding: 30px;
+            text-align: center;
+            border-top: 1px solid #e9ecef;
+        }
+
+        .footer p {
+            margin: 0 0 10px 0;
+            font-size: 14px;
+            color: #6c757d;
+        }
+
+        .footer a {
+            color: #667eea;
+            text-decoration: none;
+        }
+
+        .footer a:hover {
+            text-decoration: underline;
+        }
+
+        /* Responsive */
+        @media only screen and (max-width: 600px) {
+            .email-container {
+                margin: 0;
+                border-radius: 0;
+            }
+
+            .header, .content, .footer {
+                padding: 20px;
+            }
+
+            .logo {
+                font-size: 28px;
+            }
+
+            .content h1 {
+                font-size: 22px;
+            }
+
+            .button {
+                display: block;
+                width: 100%;
+                box-sizing: border-box;
+            }
+        }
+    </style>
+</head>
+<body>
+    <div class="email-container">
+        <div class="header">
+            <div class="logo">RentAll</div>
+            <div class="tagline">Your trusted rental marketplace</div>
+        </div>
+
+        <div class="content">
+            <h1>📸 {{title}}</h1>
+
+            <p>{{message}}</p>
+
+            <div class="info-box">
+                <div class="icon">📦</div>
+                <p><strong>Rental Item:</strong> {{itemName}}</p>
+                <p><strong>Deadline:</strong> {{deadline}}</p>
+            </div>
+
+            <p>Taking condition photos helps protect both renters and owners by providing clear documentation of the item's state. This is an important step in the rental process.</p>
+
+            <div class="alert-box">
+                <p><strong>Important:</strong> Please complete this condition check as soon as possible. Missing this deadline may affect dispute resolution if issues arise.</p>
+            </div>
+
+            <a href="#" class="button">Complete Condition Check</a>
+
+            <h2>What to photograph:</h2>
+            <ul>
+                <li>Overall view of the item</li>
+                <li>Any existing damage or wear</li>
+                <li>Serial numbers or identifying marks</li>
+                <li>Accessories or additional components</li>
+            </ul>
+
+            <p>If you have any questions about the condition check process, please don't hesitate to contact our support team.</p>
+        </div>
+
+        <div class="footer">
+            <p>&copy; 2024 RentAll. All rights reserved.</p>
+            <p>You received this email because you have an active rental on RentAll.</p>
+            <p>If you have any questions, please <a href="mailto:support@rentall.com">contact our support team</a>.</p>
+        </div>
+    </div>
+</body>
+</html>
--- a/backend/templates/emails/damageReportCS.html
+++ b/backend/templates/emails/damageReportCS.html
@@ -0,0 +1,61 @@
+<h1>Damage Report Filed - Action Required</h1>
+
+<p>Hello Customer Service Team,</p>
+
+<p>A damage report has been filed by an item owner and requires review and processing:</p>
+
+<div class="info-box">
+    <p><strong>Rental ID:</strong> {{rentalId}}</p>
+    <p><strong>Item:</strong> {{itemName}}</p>
+    <p><strong>Owner:</strong> {{ownerName}} ({{ownerEmail}})</p>
+    <p><strong>Renter:</strong> {{renterName}} ({{renterEmail}})</p>
+</div>
+
+<h2>Damage Details</h2>
+
+<div class="alert-box">
+    <p><strong>Description:</strong></p>
+    <p style="background-color: #f8f9fa; padding: 10px; border-left: 3px solid #ffc107; margin: 10px 0;">{{damageDescription}}</p>
+
+    <p><strong>Can item be fixed?</strong> {{canBeFixed}}</p>
+    {{#if repairCost}}
+    <p><strong>Repair Cost:</strong> ${{repairCost}}</p>
+    {{/if}}
+
+    <p><strong>Needs replacement?</strong> {{needsReplacement}}</p>
+    {{#if replacementCost}}
+    <p><strong>Replacement Cost:</strong> ${{replacementCost}}</p>
+    {{/if}}
+
+    <p><strong>Proof of Ownership Provided:</strong> {{hasProofOfOwnership}}</p>
+</div>
+
+<h2>Fee Summary</h2>
+
+<div class="info-box">
+    <p><strong>{{feeTypeDescription}}:</strong> ${{damageFee}}</p>
+    {{#if lateFee}}
+    <p><strong>Late Return Fee:</strong> ${{lateFee}}</p>
+    {{/if}}
+    <p style="font-size: 1.1em; border-top: 2px solid #dee2e6; padding-top: 10px; margin-top: 10px;"><strong>Total Additional Fees:</strong> ${{totalFees}}</p>
+</div>
+
+<h2>Next Steps</h2>
+
+<p>Please follow this process:</p>
+
+<ol style="color: #495057; margin: 20px 0; padding-left: 20px;">
+    <li>Review the damage description and supporting documentation (photos, proof of ownership)</li>
+    <li>Send an email to the renter ({{renterEmail}}) with the damage claim details</li>
+    <li>Include the calculated damage fee amount and breakdown</li>
+    <li>Request the renter's response and provide 48 hours to reply</li>
+    <li>If the renter agrees or does not respond within 48 hours, manually charge the damage fee through the Stripe dashboard</li>
+    <li>If the renter disputes, open a formal dispute case and review evidence from both parties</li>
+    <li>Consider requesting additional documentation if needed (repair receipts, replacement invoices)</li>
+</ol>
+
+<div class="info-box">
+    <p><strong>Note:</strong> The damage fees have NOT been automatically charged. Manual review and processing is required.</p>
+</div>
+
+<p>Thank you for your attention to this matter.</p>
--- a/backend/templates/emails/lateReturnCS.html
+++ b/backend/templates/emails/lateReturnCS.html
@@ -0,0 +1,39 @@
+<h1>Late Return Detected - Action Required</h1>
+
+<p>Hello Customer Service Team,</p>
+
+<p>A late return has been reported and requires manual processing:</p>
+
+<div class="info-box">
+    <p><strong>Rental ID:</strong> {{rentalId}}</p>
+    <p><strong>Item:</strong> {{itemName}}</p>
+    <p><strong>Owner:</strong> {{ownerName}} ({{ownerEmail}})</p>
+    <p><strong>Renter:</strong> {{renterName}} ({{renterEmail}})</p>
+</div>
+
+<h2>Return Details</h2>
+
+<div class="alert-box">
+    <p><strong>Scheduled End:</strong> {{scheduledEnd}}</p>
+    <p><strong>Actual Return:</strong> {{actualReturn}}</p>
+    <p><strong>Hours Late:</strong> {{hoursLate}}</p>
+    <p><strong>Calculated Late Fee:</strong> ${{lateFee}}</p>
+</div>
+
+<h2>Next Steps</h2>
+
+<p>Please follow this process:</p>
+
+<ol style="color: #495057; margin: 20px 0; padding-left: 20px;">
+    <li>Send an email to the renter ({{renterEmail}}) confirming the late return details</li>
+    <li>Include the calculated late fee amount and reason for the charge</li>
+    <li>Provide the renter with 48 hours to respond</li>
+    <li>If the renter agrees or does not respond within 48 hours, manually charge the late fee through the Stripe dashboard</li>
+    <li>If the renter disputes, review the case and take appropriate action</li>
+</ol>
+
+<div class="info-box">
+    <p><strong>Note:</strong> The late fee has NOT been automatically charged. Manual processing is required.</p>
+</div>
+
+<p>Thank you for your attention to this matter.</p>
--- a/backend/templates/emails/lostItemCS.html
+++ b/backend/templates/emails/lostItemCS.html
@@ -0,0 +1,40 @@
+<h1>Lost Item Claim Filed - Action Required</h1>
+
+<p>Hello Customer Service Team,</p>
+
+<p>A lost item claim has been filed by an item owner and requires review and processing:</p>
+
+<div class="info-box">
+    <p><strong>Rental ID:</strong> {{rentalId}}</p>
+    <p><strong>Item:</strong> {{itemName}}</p>
+    <p><strong>Owner:</strong> {{ownerName}} ({{ownerEmail}})</p>
+    <p><strong>Renter:</strong> {{renterName}} ({{renterEmail}})</p>
+</div>
+
+<h2>Lost Item Details</h2>
+
+<div class="alert-box">
+    <p><strong>Reported Lost At:</strong> {{reportedAt}}</p>
+    <p><strong>Scheduled Return Date:</strong> {{scheduledReturnDate}}</p>
+    <p><strong>Replacement Cost:</strong> ${{replacementCost}}</p>
+</div>
+
+<h2>Next Steps</h2>
+
+<p>Please follow this process:</p>
+
+<ol style="color: #495057; margin: 20px 0; padding-left: 20px;">
+    <li>Review the lost item claim and rental history</li>
+    <li>Send an email to the renter ({{renterEmail}}) with the lost item claim details</li>
+    <li>Include the replacement cost amount: ${{replacementCost}}</li>
+    <li>Request the renter's response and provide 48 hours to reply</li>
+    <li>If the renter agrees or does not respond within 48 hours, manually charge the replacement cost through the Stripe dashboard</li>
+    <li>If the renter disputes and claims they returned the item, open a formal dispute case and review evidence from both parties</li>
+    <li>Request proof of return from the renter if they dispute the claim</li>
+</ol>
+
+<div class="info-box">
+    <p><strong>Note:</strong> The replacement fee has NOT been automatically charged. Manual review and processing is required.</p>
+</div>
+
+<p>Thank you for your attention to this matter.</p>
--- a/backend/templates/emails/rentalConfirmation.html
+++ b/backend/templates/emails/rentalConfirmation.html
@@ -0,0 +1,281 @@
+<!DOCTYPE html>
+<html lang="en">
+<head>
+    <meta charset="utf-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1.0">
+    <meta http-equiv="X-UA-Compatible" content="IE=edge">
+    <title>{{title}}</title>
+    <style>
+        /* Reset styles */
+        body, table, td, p, a, li, blockquote {
+            -webkit-text-size-adjust: 100%;
+            -ms-text-size-adjust: 100%;
+        }
+        table, td {
+            mso-table-lspace: 0pt;
+            mso-table-rspace: 0pt;
+        }
+        img {
+            -ms-interpolation-mode: bicubic;
+        }
+
+        /* Base styles */
+        body {
+            margin: 0;
+            padding: 0;
+            width: 100% !important;
+            min-width: 100%;
+            height: 100%;
+            background-color: #f8f9fa;
+            font-family: -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, Oxygen, Ubuntu, Cantarell, sans-serif;
+            line-height: 1.6;
+            color: #212529;
+        }
+
+        /* Container */
+        .email-container {
+            max-width: 600px;
+            margin: 0 auto;
+            background-color: #ffffff;
+            border-radius: 8px;
+            overflow: hidden;
+            box-shadow: 0 4px 6px rgba(0, 0, 0, 0.1);
+        }
+
+        /* Header */
+        .header {
+            background: linear-gradient(135deg, #28a745 0%, #20c997 100%);
+            padding: 40px 30px;
+            text-align: center;
+        }
+
+        .logo {
+            font-size: 32px;
+            font-weight: 700;
+            color: #ffffff;
+            text-decoration: none;
+            letter-spacing: -1px;
+        }
+
+        .tagline {
+            color: #d4edda;
+            font-size: 14px;
+            margin-top: 8px;
+        }
+
+        /* Content */
+        .content {
+            padding: 40px 30px;
+        }
+
+        .content h1 {
+            font-size: 24px;
+            font-weight: 600;
+            margin: 0 0 20px 0;
+            color: #212529;
+        }
+
+        .content h2 {
+            font-size: 20px;
+            font-weight: 600;
+            margin: 30px 0 15px 0;
+            color: #495057;
+        }
+
+        .content p {
+            margin: 0 0 16px 0;
+            color: #6c757d;
+            line-height: 1.6;
+        }
+
+        .content strong {
+            color: #495057;
+        }
+
+        /* Button */
+        .button {
+            display: inline-block;
+            background: linear-gradient(135deg, #28a745 0%, #20c997 100%);
+            color: #ffffff !important;
+            text-decoration: none;
+            padding: 16px 32px;
+            border-radius: 6px;
+            font-weight: 600;
+            margin: 20px 0;
+            text-align: center;
+            transition: all 0.3s ease;
+        }
+
+        .button:hover {
+            transform: translateY(-2px);
+            box-shadow: 0 4px 12px rgba(40, 167, 69, 0.4);
+        }
+
+        /* Success box */
+        .success-box {
+            background-color: #d4edda;
+            border-left: 4px solid #28a745;
+            padding: 20px;
+            margin: 20px 0;
+            border-radius: 0 6px 6px 0;
+        }
+
+        .success-box p {
+            margin: 0;
+            color: #155724;
+        }
+
+        .success-box .icon {
+            font-size: 24px;
+            margin-bottom: 10px;
+        }
+
+        /* Info table */
+        .info-table {
+            width: 100%;
+            border-collapse: collapse;
+            margin: 20px 0;
+            background-color: #f8f9fa;
+            border-radius: 6px;
+            overflow: hidden;
+        }
+
+        .info-table th,
+        .info-table td {
+            padding: 15px;
+            text-align: left;
+            border-bottom: 1px solid #dee2e6;
+        }
+
+        .info-table th {
+            background-color: #e9ecef;
+            font-weight: 600;
+            color: #495057;
+        }
+
+        .info-table td {
+            color: #6c757d;
+        }
+
+        .info-table tr:last-child td {
+            border-bottom: none;
+        }
+
+        /* Footer */
+        .footer {
+            background-color: #f8f9fa;
+            padding: 30px;
+            text-align: center;
+            border-top: 1px solid #e9ecef;
+        }
+
+        .footer p {
+            margin: 0 0 10px 0;
+            font-size: 14px;
+            color: #6c757d;
+        }
+
+        .footer a {
+            color: #667eea;
+            text-decoration: none;
+        }
+
+        .footer a:hover {
+            text-decoration: underline;
+        }
+
+        /* Responsive */
+        @media only screen and (max-width: 600px) {
+            .email-container {
+                margin: 0;
+                border-radius: 0;
+            }
+
+            .header, .content, .footer {
+                padding: 20px;
+            }
+
+            .logo {
+                font-size: 28px;
+            }
+
+            .content h1 {
+                font-size: 22px;
+            }
+
+            .button {
+                display: block;
+                width: 100%;
+                box-sizing: border-box;
+            }
+
+            .info-table th,
+            .info-table td {
+                padding: 10px;
+                font-size: 14px;
+            }
+        }
+    </style>
+</head>
+<body>
+    <div class="email-container">
+        <div class="header">
+            <div class="logo">RentAll</div>
+            <div class="tagline">Rental Confirmed</div>
+        </div>
+
+        <div class="content">
+            <h1>✅ {{title}}</h1>
+
+            <p>{{message}}</p>
+
+            <div class="success-box">
+                <div class="icon">🎉</div>
+                <p><strong>Great news!</strong> Your rental has been successfully confirmed and you're all set.</p>
+            </div>
+
+            <h2>Rental Details</h2>
+            <table class="info-table">
+                <tr>
+                    <th>Item</th>
+                    <td>{{itemName}}</td>
+                </tr>
+                <tr>
+                    <th>Start Date</th>
+                    <td>{{startDate}}</td>
+                </tr>
+                <tr>
+                    <th>End Date</th>
+                    <td>{{endDate}}</td>
+                </tr>
+            </table>
+
+            <a href="#" class="button">View Rental Details</a>
+
+            <h2>What's next?</h2>
+            <ul>
+                <li><strong>Before pickup:</strong> You'll receive a reminder to take condition photos</li>
+                <li><strong>During rental:</strong> Enjoy your rental and treat it with care</li>
+                <li><strong>At return:</strong> Take photos and return the item as agreed</li>
+                <li><strong>After return:</strong> Leave a review to help the community</li>
+            </ul>
+
+            <p><strong>Important reminders:</strong></p>
+            <ul>
+                <li>Take condition photos at pickup and return</li>
+                <li>Follow any specific care instructions provided</li>
+                <li>Return the item on time and in good condition</li>
+                <li>Contact the owner if you have any questions</li>
+            </ul>
+
+            <p>Thank you for choosing RentAll! We hope you have a great rental experience.</p>
+        </div>
+
+        <div class="footer">
+            <p>&copy; 2024 RentAll. All rights reserved.</p>
+            <p>You received this email because you have a confirmed rental on RentAll.</p>
+            <p>If you have any questions, please <a href="mailto:support@rentall.com">contact our support team</a>.</p>
+        </div>
+    </div>
+</body>
+</html>
--- a/frontend/src/components/ConditionCheckModal.tsx
+++ b/frontend/src/components/ConditionCheckModal.tsx
@@ -0,0 +1,262 @@
+import React, { useState } from "react";
+import { conditionCheckAPI } from "../services/api";
+
+interface ConditionCheckModalProps {
+  show: boolean;
+  onHide: () => void;
+  rentalId: string;
+  checkType: string;
+  itemName: string;
+  onSuccess: () => void;
+}
+
+const ConditionCheckModal: React.FC<ConditionCheckModalProps> = ({
+  show,
+  onHide,
+  rentalId,
+  checkType,
+  itemName,
+  onSuccess,
+}) => {
+  const [photos, setPhotos] = useState<File[]>([]);
+  const [notes, setNotes] = useState("");
+  const [submitting, setSubmitting] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+
+  const getCheckTypeInfo = () => {
+    const types = {
+      pre_rental_owner: {
+        title: "Pre-Rental Condition",
+        description:
+          "Document the current condition of your item before the rental begins. Take clear photos showing all sides and any existing wear or damage",
+      },
+      rental_start_renter: {
+        title: "Rental Start Condition",
+        description:
+          "Document the condition of the item when you receive it. Take photos of any damage or issues you notice upon receiving the item",
+      },
+      rental_end_renter: {
+        title: "Rental End Condition",
+        description:
+          "Document the condition of the item before returning it. Take photos showing the item's condition before you return it",
+      },
+      post_rental_owner: {
+        title: "Post-Rental Condition",
+        description:
+          "Document the condition of your item after it's been returned. Take photos of the returned item including any damage or issues",
+      },
+    };
+    return (
+      types[checkType as keyof typeof types] || {
+        title: "Condition Check",
+        description: "Document the item's condition",
+      }
+    );
+  };
+
+  const typeInfo = getCheckTypeInfo();
+
+  const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
+    if (e.target.files) {
+      const selectedFiles = Array.from(e.target.files);
+      if (selectedFiles.length + photos.length > 20) {
+        setError("Maximum 20 photos allowed");
+        return;
+      }
+      setPhotos((prev) => [...prev, ...selectedFiles]);
+      setError(null);
+    }
+  };
+
+  const removePhoto = (index: number) => {
+    setPhotos((prev) => prev.filter((_, i) => i !== index));
+  };
+
+  const handleSubmit = async () => {
+    if (photos.length === 0) {
+      setError("Please upload at least one photo");
+      return;
+    }
+
+    try {
+      setSubmitting(true);
+      setError(null);
+
+      const formData = new FormData();
+      formData.append("checkType", checkType);
+      if (notes.trim()) {
+        formData.append("notes", notes.trim());
+      }
+
+      photos.forEach((photo, index) => {
+        formData.append("photos", photo);
+      });
+
+      await conditionCheckAPI.submitConditionCheck(rentalId, formData);
+
+      // Reset form
+      setPhotos([]);
+      setNotes("");
+      onSuccess();
+      onHide();
+    } catch (error: any) {
+      setError(
+        error.response?.data?.error || "Failed to submit condition check"
+      );
+    } finally {
+      setSubmitting(false);
+    }
+  };
+
+  const handleClose = () => {
+    setPhotos([]);
+    setNotes("");
+    setError(null);
+    onHide();
+  };
+
+  if (!show) return null;
+
+  return (
+    <div
+      className="modal show d-block"
+      tabIndex={-1}
+      style={{ backgroundColor: "rgba(0,0,0,0.5)" }}
+    >
+      <div className="modal-dialog modal-lg">
+        <div className="modal-content">
+          <div className="modal-header">
+            <h5 className="modal-title">
+              <i className="bi bi-camera me-2" />
+              {typeInfo.title}
+            </h5>
+            <button
+              type="button"
+              className="btn-close"
+              onClick={handleClose}
+              disabled={submitting}
+            />
+          </div>
+
+          <div className="modal-body">
+            <div className="mb-4">
+              <h6 className="text-center text-dark">{itemName}</h6>
+              <p className="text-muted mb-2">{typeInfo.description}</p>
+            </div>
+
+            {error && (
+              <div className="alert alert-danger" role="alert">
+                {error}
+              </div>
+            )}
+
+            <div className="mb-3">
+              <label className="form-label">
+                Photos <span className="text-danger">*</span>
+                <small className="text-muted ms-2">(Maximum 20 photos)</small>
+              </label>
+              <input
+                type="file"
+                className="form-control"
+                multiple
+                accept="image/*"
+                onChange={handleFileChange}
+                disabled={submitting}
+              />
+            </div>
+
+            {photos.length > 0 && (
+              <div className="mb-3">
+                <label className="form-label">
+                  Selected Photos ({photos.length})
+                </label>
+                <div className="row">
+                  {photos.map((photo, index) => (
+                    <div key={index} className="col-md-3 mb-2">
+                      <div className="position-relative">
+                        <img
+                          src={URL.createObjectURL(photo)}
+                          alt={`Photo ${index + 1}`}
+                          className="img-fluid rounded"
+                          style={{
+                            height: "100px",
+                            objectFit: "cover",
+                            width: "100%",
+                          }}
+                        />
+                        <button
+                          type="button"
+                          className="btn btn-danger btn-sm position-absolute top-0 end-0"
+                          onClick={() => removePhoto(index)}
+                          disabled={submitting}
+                          style={{ transform: "translate(50%, -50%)" }}
+                        >
+                          <i className="bi bi-x" />
+                        </button>
+                      </div>
+                      <small className="text-muted d-block text-center mt-1">
+                        {photo.name.length > 15
+                          ? `${photo.name.substring(0, 15)}...`
+                          : photo.name}
+                      </small>
+                    </div>
+                  ))}
+                </div>
+              </div>
+            )}
+
+            <div className="mb-3">
+              <label className="form-label">Notes (Optional)</label>
+              <textarea
+                className="form-control"
+                rows={3}
+                value={notes}
+                onChange={(e) => setNotes(e.target.value)}
+                placeholder="Add any additional notes about the item's condition"
+                maxLength={500}
+                disabled={submitting}
+              />
+              <div className="form-text">{notes.length}/500 characters</div>
+            </div>
+          </div>
+
+          <div className="modal-footer">
+            <button
+              type="button"
+              className="btn btn-secondary"
+              onClick={handleClose}
+              disabled={submitting}
+            >
+              Cancel
+            </button>
+            <button
+              type="button"
+              className="btn btn-primary"
+              onClick={handleSubmit}
+              disabled={submitting || photos.length === 0}
+            >
+              {submitting ? (
+                <>
+                  <div
+                    className="spinner-border spinner-border-sm me-2"
+                    role="status"
+                  >
+                    <span className="visually-hidden">Loading...</span>
+                  </div>
+                  Submitting...
+                </>
+              ) : (
+                <>
+                  <i className="bi bi-check-lg me-2" />
+                  Submit Condition Check
+                </>
+              )}
+            </button>
+          </div>
+        </div>
+      </div>
+    </div>
+  );
+};
+
+export default ConditionCheckModal;
--- a/frontend/src/components/ReturnStatusModal.tsx
+++ b/frontend/src/components/ReturnStatusModal.tsx
@@ -0,0 +1,954 @@
+import React, { useState, useEffect, useCallback } from "react";
+import { rentalAPI, conditionCheckAPI } from "../services/api";
+import { Rental } from "../types";
+
+interface ReturnStatusModalProps {
+  show: boolean;
+  onHide: () => void;
+  rental: Rental;
+  onReturnMarked: (updatedRental: Rental) => void;
+  onSubmitSuccess?: (updatedRental: Rental) => void;
+}
+
+const ReturnStatusModal: React.FC<ReturnStatusModalProps> = ({
+  show,
+  onHide,
+  rental,
+  onReturnMarked,
+  onSubmitSuccess,
+}) => {
+  const [statusOptions, setStatusOptions] = useState({
+    returned: false,
+    returned_late: false,
+    damaged: false,
+    lost: false,
+  });
+  const [actualReturnDateTime, setActualReturnDateTime] = useState("");
+  const [notes, setNotes] = useState("");
+  const [conditionNotes, setConditionNotes] = useState("");
+  const [photos, setPhotos] = useState<File[]>([]);
+  const [processing, setProcessing] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+  const [lateFeeCalculation, setLateFeeCalculation] = useState<{
+    lateHours: number;
+    lateFee: number;
+    isLate: boolean;
+    pricingType?: "hourly" | "daily";
+    billableDays?: number;
+  } | null>(null);
+
+  // Damage assessment fields
+  const [canBeFixed, setCanBeFixed] = useState<boolean | null>(null);
+  const [repairCost, setRepairCost] = useState("");
+  const [needsReplacement, setNeedsReplacement] = useState<boolean | null>(
+    null
+  );
+  const [replacementCost, setReplacementCost] = useState("");
+  const [proofOfOwnership, setProofOfOwnership] = useState<File[]>([]);
+
+  // Initialize form when modal opens
+  useEffect(() => {
+    if (show && rental) {
+      setStatusOptions({
+        returned: false,
+        returned_late: false,
+        damaged: false,
+        lost: false,
+      });
+      setActualReturnDateTime("");
+      setNotes("");
+      setConditionNotes("");
+      setPhotos([]);
+      setError(null);
+      setLateFeeCalculation(null);
+      setCanBeFixed(null);
+      setRepairCost("");
+      setNeedsReplacement(null);
+      setReplacementCost("");
+      setProofOfOwnership([]);
+    }
+  }, [show, rental]);
+
+  const formatCurrency = (amount: number | string | undefined) => {
+    const numAmount = Number(amount) || 0;
+    return `$${numAmount.toFixed(2)}`;
+  };
+
+  const formatDateTime = (date: Date) => {
+    // Format for datetime-local input in local timezone
+    const year = date.getFullYear();
+    const month = String(date.getMonth() + 1).padStart(2, "0");
+    const day = String(date.getDate()).padStart(2, "0");
+    const hours = String(date.getHours()).padStart(2, "0");
+    const minutes = String(date.getMinutes()).padStart(2, "0");
+    return `${year}-${month}-${day}T${hours}:${minutes}`;
+  };
+
+  // Calculate late fee when actual return date/time changes
+  useEffect(() => {
+    const fetchLateFeeCalculation = async () => {
+      if (statusOptions.returned_late && actualReturnDateTime && rental) {
+        try {
+          const response = await rentalAPI.getLateFeePreview(
+            rental.id,
+            actualReturnDateTime
+          );
+          setLateFeeCalculation(response.data);
+        } catch (error) {
+          console.error("Error fetching late fee calculation:", error);
+          setLateFeeCalculation(null);
+        }
+      } else {
+        setLateFeeCalculation(null);
+      }
+    };
+
+    fetchLateFeeCalculation();
+  }, [actualReturnDateTime, statusOptions.returned_late, rental]);
+
+  const handleStatusChange = (
+    statusType: "returned" | "returned_late" | "damaged" | "lost",
+    checked: boolean
+  ) => {
+    setStatusOptions((prev) => {
+      const newOptions = { ...prev };
+
+      // Apply the change
+      newOptions[statusType] = checked;
+
+      // Apply mutual exclusion logic
+      if (statusType === "returned" && checked) {
+        newOptions.returned_late = false;
+        newOptions.lost = false;
+      }
+      if (statusType === "returned_late" && checked) {
+        newOptions.returned = false;
+        newOptions.lost = false;
+        // Set default return time for late returns
+        if (!actualReturnDateTime) {
+          setActualReturnDateTime(formatDateTime(new Date()));
+        }
+      }
+      if (statusType === "damaged" && checked) {
+        newOptions.lost = false;
+      }
+      if (statusType === "lost" && checked) {
+        // If item is lost, uncheck all other options
+        newOptions.returned = false;
+        newOptions.returned_late = false;
+        newOptions.damaged = false;
+      }
+
+      return newOptions;
+    });
+  };
+
+  const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
+    if (e.target.files) {
+      const selectedFiles = Array.from(e.target.files);
+      if (selectedFiles.length + photos.length > 20) {
+        setError("Maximum 20 photos allowed");
+        return;
+      }
+      setPhotos((prev) => [...prev, ...selectedFiles]);
+      setError(null);
+    }
+  };
+
+  const removePhoto = (index: number) => {
+    setPhotos((prev) => prev.filter((_, i) => i !== index));
+  };
+
+  const handleProofOfOwnershipChange = (
+    e: React.ChangeEvent<HTMLInputElement>
+  ) => {
+    if (e.target.files) {
+      const selectedFiles = Array.from(e.target.files);
+      if (selectedFiles.length + proofOfOwnership.length > 5) {
+        setError("Maximum 5 proof of ownership files allowed");
+        return;
+      }
+      setProofOfOwnership((prev) => [...prev, ...selectedFiles]);
+      setError(null);
+    }
+  };
+
+  const removeProofOfOwnership = (index: number) => {
+    setProofOfOwnership((prev) => prev.filter((_, i) => i !== index));
+  };
+
+  const handleSubmit = async () => {
+    if (!rental) return;
+
+    try {
+      setProcessing(true);
+      setError(null);
+
+      // Check if at least one option is selected
+      const hasSelection = Object.values(statusOptions).some(
+        (option) => option
+      );
+      if (!hasSelection) {
+        setError("Please select at least one return status option");
+        return;
+      }
+
+      // Validate required fields
+      if (statusOptions.returned_late && !actualReturnDateTime) {
+        setError("Please provide the actual return date and time");
+        setProcessing(false);
+        return;
+      }
+
+      // Validate damage assessment fields if damaged is selected
+      if (statusOptions.damaged) {
+        if (!conditionNotes.trim() || conditionNotes.trim().length < 10) {
+          setError(
+            "Please provide a detailed damage description (at least 10 characters)"
+          );
+          setProcessing(false);
+          return;
+        }
+
+        if (canBeFixed === null) {
+          setError("Please specify if the item can be fixed");
+          setProcessing(false);
+          return;
+        }
+
+        if (canBeFixed && (!repairCost || parseFloat(repairCost) <= 0)) {
+          setError("Please provide a repair cost estimate");
+          setProcessing(false);
+          return;
+        }
+
+        if (needsReplacement === null) {
+          setError("Please specify if the item needs replacement");
+          setProcessing(false);
+          return;
+        }
+
+        if (
+          needsReplacement &&
+          (!replacementCost || parseFloat(replacementCost) <= 0)
+        ) {
+          setError("Please provide a replacement cost");
+          setProcessing(false);
+          return;
+        }
+      }
+
+      let response;
+
+      // If damaged is selected, use reportDamage API
+      if (statusOptions.damaged) {
+        const damageFormData = new FormData();
+        damageFormData.append("description", conditionNotes.trim());
+        damageFormData.append("canBeFixed", canBeFixed?.toString() || "false");
+        damageFormData.append(
+          "needsReplacement",
+          needsReplacement?.toString() || "false"
+        );
+
+        if (canBeFixed) {
+          damageFormData.append("repairCost", repairCost);
+        }
+
+        if (needsReplacement) {
+          damageFormData.append("replacementCost", replacementCost);
+        }
+
+        if (actualReturnDateTime) {
+          damageFormData.append("actualReturnDateTime", actualReturnDateTime);
+        }
+
+        // Add condition photos
+        photos.forEach((photo) => {
+          damageFormData.append("photos", photo);
+        });
+
+        // Add proof of ownership files
+        proofOfOwnership.forEach((file) => {
+          damageFormData.append("proofOfOwnership", file);
+        });
+
+        response = await rentalAPI.reportDamage(rental.id, damageFormData);
+      } else {
+        // Non-damaged returns: use existing flow
+
+        // Submit post-rental condition check if photos are provided
+        if (photos.length > 0) {
+          const conditionCheckFormData = new FormData();
+          conditionCheckFormData.append("checkType", "post_rental_owner");
+          if (conditionNotes.trim()) {
+            conditionCheckFormData.append("notes", conditionNotes.trim());
+          }
+          photos.forEach((photo) => {
+            conditionCheckFormData.append("photos", photo);
+          });
+
+          await conditionCheckAPI.submitConditionCheck(
+            rental.id,
+            conditionCheckFormData
+          );
+        }
+
+        // Determine primary status for API call
+        let primaryStatus = "returned";
+        if (statusOptions.returned_late) {
+          primaryStatus = "returned_late";
+        } else if (statusOptions.lost) {
+          primaryStatus = "lost";
+        }
+
+        const data: any = {
+          status: primaryStatus,
+          statusOptions, // Send all selected options
+          notes: notes.trim() || undefined,
+        };
+
+        if (statusOptions.returned_late) {
+          data.actualReturnDateTime = actualReturnDateTime;
+        }
+
+        response = await rentalAPI.markReturn(rental.id, data);
+      }
+
+      // Call success callback and close modal immediately
+      if (onSubmitSuccess) {
+        onSubmitSuccess(response.data.rental);
+      }
+      onHide();
+    } catch (error: any) {
+      setError(error.response?.data?.error || "Failed to mark return status");
+      setProcessing(false);
+    }
+  };
+
+  const handleClose = () => {
+    // Reset all states
+    setStatusOptions({
+      returned: false,
+      returned_late: false,
+      damaged: false,
+      lost: false,
+    });
+    setActualReturnDateTime("");
+    setNotes("");
+    setConditionNotes("");
+    setPhotos([]);
+    setError(null);
+    setLateFeeCalculation(null);
+    setCanBeFixed(null);
+    setRepairCost("");
+    setNeedsReplacement(null);
+    setReplacementCost("");
+    setProofOfOwnership([]);
+    onHide();
+  };
+
+  const handleBackdropClick = useCallback(
+    (e: React.MouseEvent) => {
+      if (e.target === e.currentTarget) {
+        handleClose();
+      }
+    },
+    [handleClose]
+  );
+
+  const handleKeyDown = useCallback(
+    (e: KeyboardEvent) => {
+      if (e.key === "Escape") {
+        handleClose();
+      }
+    },
+    [handleClose]
+  );
+
+  useEffect(() => {
+    if (show) {
+      document.addEventListener("keydown", handleKeyDown);
+      document.body.style.overflow = "hidden";
+    } else {
+      document.removeEventListener("keydown", handleKeyDown);
+      document.body.style.overflow = "unset";
+    }
+
+    return () => {
+      document.removeEventListener("keydown", handleKeyDown);
+      document.body.style.overflow = "unset";
+    };
+  }, [show, handleKeyDown]);
+
+  if (!show) return null;
+
+  return (
+    <div
+      className="modal d-block"
+      style={{ backgroundColor: "rgba(0,0,0,0.5)" }}
+      onClick={handleBackdropClick}
+    >
+      <div className="modal-dialog modal-lg modal-dialog-centered">
+        <div className="modal-content">
+          <div className="modal-header">
+            <h5 className="modal-title">Item Return</h5>
+            <button
+              type="button"
+              className="btn-close"
+              onClick={handleClose}
+              aria-label="Close"
+            />
+          </div>
+
+          <div className="modal-body">
+            {error && (
+              <div className="alert alert-danger mb-3" role="alert">
+                {error}
+              </div>
+            )}
+
+            <div className="mb-4">
+              <h5>Rental Information</h5>
+              <div className="bg-light p-3 rounded">
+                <div className="row">
+                  <div className="col-md-6">
+                    <p className="mb-2">
+                      <strong>Item:</strong> {rental.item?.name}
+                    </p>
+                    <p className="mb-2">
+                      <strong>Renter:</strong> {rental.renter?.firstName}{" "}
+                      {rental.renter?.lastName}
+                    </p>
+                  </div>
+                  <div className="col-md-6">
+                    <p className="mb-2">
+                      <strong>Scheduled End:</strong>
+                      <br />
+                      {new Date(rental.endDateTime).toLocaleString()}
+                    </p>
+                  </div>
+                </div>
+              </div>
+            </div>
+
+            <form>
+              <div className="mb-4">
+                <label className="form-label">
+                  <strong>Return Status</strong>
+                </label>
+
+                <div className="row g-3">
+                  <div className="col-md-6">
+                    <div className="form-check">
+                      <input
+                        className="form-check-input"
+                        type="checkbox"
+                        id="returned"
+                        checked={statusOptions.returned}
+                        onChange={(e) =>
+                          handleStatusChange("returned", e.target.checked)
+                        }
+                      />
+                      <label className="form-check-label" htmlFor="returned">
+                        <i className="bi bi-check-circle me-2 text-success" />
+                        Item Returned On Time
+                      </label>
+                    </div>
+                  </div>
+
+                  <div className="col-md-6">
+                    <div className="form-check">
+                      <input
+                        className="form-check-input"
+                        type="checkbox"
+                        id="returned_late"
+                        checked={statusOptions.returned_late}
+                        onChange={(e) =>
+                          handleStatusChange("returned_late", e.target.checked)
+                        }
+                      />
+                      <label
+                        className="form-check-label"
+                        htmlFor="returned_late"
+                      >
+                        <i className="bi bi-clock me-2 text-warning" />
+                        Item Returned Late
+                      </label>
+                    </div>
+                  </div>
+
+                  <div className="col-md-6">
+                    <div className="form-check">
+                      <input
+                        className="form-check-input"
+                        type="checkbox"
+                        id="damaged"
+                        checked={statusOptions.damaged}
+                        onChange={(e) =>
+                          handleStatusChange("damaged", e.target.checked)
+                        }
+                      />
+                      <label className="form-check-label" htmlFor="damaged">
+                        <i className="bi bi-exclamation-triangle me-2 text-warning" />
+                        Item Damaged
+                      </label>
+                    </div>
+                  </div>
+
+                  <div className="col-md-6">
+                    <div className="form-check">
+                      <input
+                        className="form-check-input"
+                        type="checkbox"
+                        id="lost"
+                        checked={statusOptions.lost}
+                        onChange={(e) =>
+                          handleStatusChange("lost", e.target.checked)
+                        }
+                      />
+                      <label className="form-check-label" htmlFor="lost">
+                        <i className="bi bi-x-circle me-2 text-danger" />
+                        Item Lost
+                      </label>
+                    </div>
+                  </div>
+                </div>
+              </div>
+
+              {statusOptions.returned_late && (
+                <>
+                  <div className="mb-4">
+                    <label
+                      className="form-label"
+                      htmlFor="actualReturnDateTime"
+                    >
+                      <strong>Actual Return Date & Time</strong>
+                    </label>
+                    <div className="form-text mb-2">
+                      When was the item actually returned to you?
+                    </div>
+                    <input
+                      type="datetime-local"
+                      id="actualReturnDateTime"
+                      className="form-control"
+                      value={actualReturnDateTime}
+                      onChange={(e) => setActualReturnDateTime(e.target.value)}
+                      max={formatDateTime(new Date())}
+                      required
+                    />
+                  </div>
+
+                  {actualReturnDateTime && lateFeeCalculation && (
+                    <div className="alert alert-warning mb-4">
+                      <h6>
+                        <i className="bi bi-exclamation-circle me-2" />
+                        Late Fee Calculation
+                      </h6>
+                      {lateFeeCalculation.isLate ? (
+                        <>
+                          <div className="mb-2">
+                            <strong>Time Overdue:</strong>{" "}
+                            {lateFeeCalculation.lateHours < 24
+                              ? `${lateFeeCalculation.lateHours.toFixed(
+                                  1
+                                )} hours`
+                              : `${Math.floor(
+                                  lateFeeCalculation.lateHours / 24
+                                )} days ${Math.floor(
+                                  lateFeeCalculation.lateHours % 24
+                                )} hours`}
+                          </div>
+                          {lateFeeCalculation.pricingType === "hourly" && (
+                            <div className="mb-2">
+                              <strong>Calculation:</strong>{" "}
+                              {lateFeeCalculation.lateHours.toFixed(1)} hours ×{" "}
+                              {formatCurrency(rental.item?.pricePerHour)} per
+                              hour
+                            </div>
+                          )}
+                          {lateFeeCalculation.pricingType === "daily" &&
+                            lateFeeCalculation.billableDays && (
+                              <div className="mb-2">
+                                <strong>Calculation:</strong>{" "}
+                                {lateFeeCalculation.billableDays} billable day
+                                {lateFeeCalculation.billableDays > 1
+                                  ? "s"
+                                  : ""}{" "}
+                                × {formatCurrency(rental.item?.pricePerDay)} per
+                                day
+                              </div>
+                            )}
+                          <div className="mb-2">
+                            <strong>Estimated Late Fee:</strong>{" "}
+                            {formatCurrency(lateFeeCalculation.lateFee)}
+                          </div>
+                          <small className="text-muted">
+                            Customer service will contact the renter to confirm
+                            the late return. If the renter agrees or does not
+                            respond within 48 hours, the late fee will be
+                            charged manually.
+                          </small>
+                        </>
+                      ) : (
+                        <p className="mb-0 text-success">
+                          <i className="bi bi-check-circle me-2" />
+                          Item was returned on time - no late fee.
+                        </p>
+                      )}
+                    </div>
+                  )}
+                </>
+              )}
+
+              {!statusOptions.lost && (
+                <>
+                  <div className="mb-4">
+                    <label className="form-label">
+                      <strong>Post-Rental Condition</strong>{" "}
+                      <small className="text-muted ms-2">(Optional)</small>
+                    </label>
+                    <div className="form-text mb-2">
+                      Document the condition of the item
+                    </div>
+                    <input
+                      type="file"
+                      className="form-control"
+                      multiple
+                      accept="image/*"
+                      onChange={handleFileChange}
+                      disabled={processing}
+                    />
+                  </div>
+
+                  {photos.length > 0 && (
+                    <div className="mb-4">
+                      <label className="form-label">
+                        Selected Photos ({photos.length})
+                      </label>
+                      <div className="row">
+                        {photos.map((photo, index) => (
+                          <div key={index} className="col-md-3 mb-2">
+                            <div className="position-relative">
+                              <img
+                                src={URL.createObjectURL(photo)}
+                                alt={`Photo ${index + 1}`}
+                                className="img-fluid rounded"
+                                style={{
+                                  height: "100px",
+                                  objectFit: "cover",
+                                  width: "100%",
+                                }}
+                              />
+                              <button
+                                type="button"
+                                className="btn btn-danger btn-sm position-absolute top-0 end-0"
+                                onClick={() => removePhoto(index)}
+                                disabled={processing}
+                                style={{ transform: "translate(50%, -50%)" }}
+                              >
+                                <i className="bi bi-x" />
+                              </button>
+                            </div>
+                            <small className="text-muted d-block text-center mt-1">
+                              {photo.name.length > 15
+                                ? `${photo.name.substring(0, 15)}...`
+                                : photo.name}
+                            </small>
+                          </div>
+                        ))}
+                      </div>
+                    </div>
+                  )}
+
+                  <div className="mb-4">
+                    <label className="form-label" htmlFor="conditionNotes">
+                      <strong>
+                        {statusOptions.damaged
+                          ? "Damage Description"
+                          : "Condition Notes"}
+                      </strong>
+                      {statusOptions.damaged ? (
+                        <span className="text-danger ms-1">*</span>
+                      ) : (
+                        <span className="text-muted ms-1">(Optional)</span>
+                      )}
+                    </label>
+                    <textarea
+                      id="conditionNotes"
+                      className="form-control"
+                      rows={3}
+                      value={conditionNotes}
+                      onChange={(e) => setConditionNotes(e.target.value)}
+                      placeholder={
+                        statusOptions.damaged
+                          ? "Describe the damage in detail..."
+                          : "Add any notes about the item's condition..."
+                      }
+                      maxLength={500}
+                      disabled={processing}
+                      required={statusOptions.damaged}
+                    />
+                    <div className="form-text">
+                      {conditionNotes.length}/500 characters
+                      {statusOptions.damaged && " (minimum 10 required)"}
+                    </div>
+                  </div>
+                </>
+              )}
+
+              {statusOptions.lost && (
+                <div className="mb-4">
+                  <div className="alert alert-danger">
+                    <h6>
+                      <i className="bi bi-exclamation-triangle me-2" />
+                      Lost Item Claim
+                    </h6>
+                    <div className="mb-3">
+                      <strong>Replacement Cost:</strong>{" "}
+                      {formatCurrency(rental.item?.replacementCost)}
+                    </div>
+                    <p className="mb-2">
+                      Customer service will review this lost item claim and
+                      contact both you and the renter.
+                    </p>
+                  </div>
+                </div>
+              )}
+
+              {statusOptions.damaged && (
+                <div className="mb-4">
+                  <div className="alert alert-warning">
+                    <div className="mb-3">
+                      <label className="form-label">
+                        <strong>Can item be fixed?</strong>
+                      </label>
+                      <div>
+                        <div className="form-check form-check-inline">
+                          <input
+                            className="form-check-input"
+                            type="radio"
+                            name="canBeFixed"
+                            id="canBeFixedYes"
+                            checked={canBeFixed === true}
+                            onChange={() => setCanBeFixed(true)}
+                            disabled={processing}
+                          />
+                          <label
+                            className="form-check-label"
+                            htmlFor="canBeFixedYes"
+                          >
+                            Yes
+                          </label>
+                        </div>
+                        <div className="form-check form-check-inline">
+                          <input
+                            className="form-check-input"
+                            type="radio"
+                            name="canBeFixed"
+                            id="canBeFixedNo"
+                            checked={canBeFixed === false}
+                            onChange={() => setCanBeFixed(false)}
+                            disabled={processing}
+                          />
+                          <label
+                            className="form-check-label"
+                            htmlFor="canBeFixedNo"
+                          >
+                            No
+                          </label>
+                        </div>
+                      </div>
+                    </div>
+
+                    {canBeFixed === true && (
+                      <div className="mb-3">
+                        <label className="form-label" htmlFor="repairCost">
+                          <strong>Repair Cost</strong>{" "}
+                          <span className="text-danger">*</span>
+                        </label>
+                        <div className="input-group">
+                          <span className="input-group-text">$</span>
+                          <input
+                            type="number"
+                            id="repairCost"
+                            className="form-control"
+                            value={repairCost}
+                            onChange={(e) => setRepairCost(e.target.value)}
+                            placeholder="0.00"
+                            min="0"
+                            step="0.01"
+                            disabled={processing}
+                            required
+                          />
+                        </div>
+                      </div>
+                    )}
+
+                    <div className="mb-3">
+                      <label className="form-label">
+                        <strong>Does item need replacement?</strong>
+                      </label>
+                      <div>
+                        <div className="form-check form-check-inline">
+                          <input
+                            className="form-check-input"
+                            type="radio"
+                            name="needsReplacement"
+                            id="needsReplacementYes"
+                            checked={needsReplacement === true}
+                            onChange={() => setNeedsReplacement(true)}
+                            disabled={processing}
+                          />
+                          <label
+                            className="form-check-label"
+                            htmlFor="needsReplacementYes"
+                          >
+                            Yes
+                          </label>
+                        </div>
+                        <div className="form-check form-check-inline">
+                          <input
+                            className="form-check-input"
+                            type="radio"
+                            name="needsReplacement"
+                            id="needsReplacementNo"
+                            checked={needsReplacement === false}
+                            onChange={() => setNeedsReplacement(false)}
+                            disabled={processing}
+                          />
+                          <label
+                            className="form-check-label"
+                            htmlFor="needsReplacementNo"
+                          >
+                            No
+                          </label>
+                        </div>
+                      </div>
+                    </div>
+
+                    {needsReplacement === true && (
+                      <div className="mb-3">
+                        <label className="form-label" htmlFor="replacementCost">
+                          <strong>Replacement Cost</strong>{" "}
+                          <span className="text-danger">*</span>
+                        </label>
+                        <div className="input-group">
+                          <span className="input-group-text">$</span>
+                          <input
+                            type="number"
+                            id="replacementCost"
+                            className="form-control"
+                            value={replacementCost}
+                            onChange={(e) => setReplacementCost(e.target.value)}
+                            placeholder="0.00"
+                            min="0"
+                            step="0.01"
+                            disabled={processing}
+                            required
+                          />
+                        </div>
+                      </div>
+                    )}
+
+                    <div className="mb-3">
+                      <label className="form-label">
+                        <strong>Proof of Ownership</strong>{" "}
+                        <small className="text-muted">(Optional)</small>
+                      </label>
+                      <div className="form-text mb-2">
+                        Upload receipts, invoices, or other documents showing
+                        proof of ownership
+                      </div>
+                      <input
+                        type="file"
+                        className="form-control"
+                        multiple
+                        accept="image/*,.pdf"
+                        onChange={handleProofOfOwnershipChange}
+                        disabled={processing}
+                      />
+                    </div>
+
+                    {proofOfOwnership.length > 0 && (
+                      <div className="mb-3">
+                        <label className="form-label">
+                          Proof of Ownership Files ({proofOfOwnership.length})
+                        </label>
+                        <ul className="list-group">
+                          {proofOfOwnership.map((file, index) => (
+                            <li
+                              key={index}
+                              className="list-group-item d-flex justify-content-between align-items-center"
+                            >
+                              <span>
+                                <i className="bi bi-file-earmark me-2" />
+                                {file.name.length > 40
+                                  ? `${file.name.substring(0, 40)}...`
+                                  : file.name}
+                              </span>
+                              <button
+                                type="button"
+                                className="btn btn-sm btn-danger"
+                                onClick={() => removeProofOfOwnership(index)}
+                                disabled={processing}
+                              >
+                                <i className="bi bi-x" />
+                              </button>
+                            </li>
+                          ))}
+                        </ul>
+                      </div>
+                    )}
+
+                    <small className="text-muted">
+                      <i className="bi bi-info-circle me-1" />
+                      Customer service will review this damage claim and contact
+                      you if additional information is needed.
+                    </small>
+                  </div>
+                </div>
+              )}
+            </form>
+          </div>
+
+          <div className="modal-footer">
+            <button
+              type="button"
+              className="btn btn-secondary"
+              onClick={handleClose}
+              disabled={processing}
+            >
+              Cancel
+            </button>
+
+            <button
+              type="button"
+              className="btn btn-primary"
+              onClick={handleSubmit}
+              disabled={
+                processing ||
+                (statusOptions.returned_late && !actualReturnDateTime)
+              }
+            >
+              {processing ? (
+                <>
+                  <div
+                    className="spinner-border spinner-border-sm me-2"
+                    role="status"
+                  >
+                    <span className="visually-hidden">Loading...</span>
+                  </div>
+                  Processing...
+                </>
+              ) : (
+                "Submit"
+              )}
+            </button>
+          </div>
+        </div>
+      </div>
+    </div>
+  );
+};
+
+export default ReturnStatusModal;
--- a/frontend/src/contexts/AuthContext.tsx
+++ b/frontend/src/contexts/AuthContext.tsx
@@ -6,7 +6,12 @@ import React, {
  ReactNode,
 } from "react";
 import { User } from "../types";
-import { authAPI, userAPI, fetchCSRFToken, resetCSRFToken, hasAuthIndicators } from "../services/api";
+import {
+  authAPI,
+  userAPI,
+  fetchCSRFToken,
+  resetCSRFToken,
+} from "../services/api";

 interface AuthContextType {
  user: User | null;
@@ -39,13 +44,14 @@ export const AuthProvider: React.FC<AuthProviderProps> = ({ children }) => {

  const checkAuth = async () => {
    try {
+      // The axios interceptor will automatically handle token refresh if needed
      const response = await userAPI.getProfile();
      setUser(response.data);
    } catch (error: any) {
-      // Only log actual errors, not "user not logged in"
-      if (error.response?.data?.code !== "NO_TOKEN") {
-        console.error("Auth check failed:", error);
-      }
+      // If we get here, either:
+      // 1. User is not logged in (expected for public browsing)
+      // 2. Token refresh failed (user needs to login again)
+      // In both cases, silently set user to null without logging errors
      setUser(null);
    }
  };
@@ -54,26 +60,11 @@ export const AuthProvider: React.FC<AuthProviderProps> = ({ children }) => {
    // Initialize authentication
    const initializeAuth = async () => {
      try {
-        // Check if we have any auth indicators before making API call
-        if (hasAuthIndicators()) {
-          // Only check auth if we have some indication of being logged in
-          // This avoids unnecessary 401 errors in the console
+        await fetchCSRFToken();
+        // Check if user is already authenticated
        await checkAuth();
-        } else {
-          // No auth indicators - skip the API call
-          setUser(null);
-        }
-
-        // Always fetch CSRF token for subsequent requests
-        await fetchCSRFToken();
      } catch (error) {
-        console.error("Failed to initialize auth:", error);
-        // Even on error, try to get CSRF token for non-authenticated requests
-        try {
-          await fetchCSRFToken();
-        } catch (csrfError) {
-          console.error("Failed to fetch CSRF token:", csrfError);
-        }
+        console.error("Failed to initialize authentication:", error);
      } finally {
        setLoading(false);
      }
--- a/frontend/src/pages/MyListings.tsx
+++ b/frontend/src/pages/MyListings.tsx
@@ -3,9 +3,11 @@ import { Link, useNavigate } from "react-router-dom";
 import { useAuth } from "../contexts/AuthContext";
 import api from "../services/api";
 import { Item, Rental } from "../types";
-import { rentalAPI } from "../services/api";
+import { rentalAPI, conditionCheckAPI } from "../services/api";
 import ReviewRenterModal from "../components/ReviewRenterModal";
 import RentalCancellationModal from "../components/RentalCancellationModal";
+import ConditionCheckModal from "../components/ConditionCheckModal";
+import ReturnStatusModal from "../components/ReturnStatusModal";

 const MyListings: React.FC = () => {
  // Helper function to format time
@@ -24,8 +26,17 @@ const MyListings: React.FC = () => {

  // Helper function to format date and time together
  const formatDateTime = (dateTimeString: string) => {
-    const date = new Date(dateTimeString).toLocaleDateString();
-    return date;
+    const date = new Date(dateTimeString);
+    return date
+      .toLocaleDateString("en-US", {
+        month: "2-digit",
+        day: "2-digit",
+        year: "numeric",
+        hour: "numeric",
+        minute: "2-digit",
+        hour12: true,
+      })
+      .replace(",", "");
  };

  const { user } = useAuth();
@@ -42,12 +53,28 @@ const MyListings: React.FC = () => {
  const [rentalToCancel, setRentalToCancel] = useState<Rental | null>(null);
  const [isProcessingPayment, setIsProcessingPayment] = useState<string>("");
  const [processingSuccess, setProcessingSuccess] = useState<string>("");
+  const [showConditionCheckModal, setShowConditionCheckModal] = useState(false);
+  const [conditionCheckData, setConditionCheckData] = useState<{
+    rental: Rental;
+    checkType: string;
+  } | null>(null);
+  const [availableChecks, setAvailableChecks] = useState<any[]>([]);
+  const [conditionChecks, setConditionChecks] = useState<any[]>([]);
+  const [showReturnStatusModal, setShowReturnStatusModal] = useState(false);
+  const [rentalForReturn, setRentalForReturn] = useState<Rental | null>(null);

  useEffect(() => {
    fetchMyListings();
    fetchOwnerRentals();
+    fetchAvailableChecks();
  }, [user]);

+  useEffect(() => {
+    if (ownerRentals.length > 0) {
+      fetchConditionChecks();
+    }
+  }, [ownerRentals]);
+
  const fetchMyListings = async () => {
    if (!user) return;

@@ -108,6 +135,44 @@ const MyListings: React.FC = () => {
    }
  };

+  const fetchAvailableChecks = async () => {
+    try {
+      const response = await conditionCheckAPI.getAvailableChecks();
+      const checks = Array.isArray(response.data.availableChecks)
+        ? response.data.availableChecks
+        : [];
+      setAvailableChecks(checks);
+    } catch (err: any) {
+      console.error("Failed to fetch available checks:", err);
+      setAvailableChecks([]);
+    }
+  };
+
+  const fetchConditionChecks = async () => {
+    try {
+      // Fetch condition checks for all owner rentals
+      const allChecks: any[] = [];
+      for (const rental of ownerRentals) {
+        try {
+          const response = await conditionCheckAPI.getConditionChecks(
+            rental.id
+          );
+          const checks = Array.isArray(response.data.conditionChecks)
+            ? response.data.conditionChecks
+            : [];
+          allChecks.push(...checks);
+        } catch (err) {
+          // Continue even if one rental fails
+          console.error(`Failed to fetch checks for rental ${rental.id}:`, err);
+        }
+      }
+      setConditionChecks(allChecks);
+    } catch (err: any) {
+      console.error("Failed to fetch condition checks:", err);
+      setConditionChecks([]);
+    }
+  };
+
  // Owner functionality handlers
  const handleAcceptRental = async (rentalId: string) => {
    try {
@@ -127,6 +192,7 @@ const MyListings: React.FC = () => {
      }

      fetchOwnerRentals();
+      fetchAvailableChecks(); // Refresh available checks after rental confirmation
    } catch (err: any) {
      console.error("Failed to accept rental request:", err);

@@ -155,21 +221,27 @@ const MyListings: React.FC = () => {
    }
  };

-  const handleCompleteClick = async (rental: Rental) => {
-    try {
-      await rentalAPI.markAsCompleted(rental.id);
+  const handleCompleteClick = (rental: Rental) => {
+    setRentalForReturn(rental);
+    setShowReturnStatusModal(true);
+  };

-      setSelectedRentalForReview(rental);
-      setShowReviewRenterModal(true);
-
-      fetchOwnerRentals();
-    } catch (err: any) {
-      console.error("Error marking rental as completed:", err);
-      alert(
-        "Failed to mark rental as completed: " +
-          (err.response?.data?.error || err.message)
+  const handleReturnStatusMarked = async (updatedRental: Rental) => {
+    // Update the rental in the list
+    setOwnerRentals((prev) =>
+      prev.map((rental) =>
+        rental.id === updatedRental.id ? updatedRental : rental
+      )
    );
-    }
+
+    // Close the return status modal
+    setShowReturnStatusModal(false);
+    setRentalForReturn(null);
+
+    // Show review modal (rental is already marked as completed by return status endpoint)
+    setSelectedRentalForReview(updatedRental);
+    setShowReviewRenterModal(true);
+    fetchOwnerRentals();
  };

  const handleReviewRenterSuccess = () => {
@@ -192,6 +264,35 @@ const MyListings: React.FC = () => {
    setRentalToCancel(null);
  };

+  const handleConditionCheck = (rental: Rental, checkType: string) => {
+    setConditionCheckData({ rental, checkType });
+    setShowConditionCheckModal(true);
+  };
+
+  const handleConditionCheckSuccess = () => {
+    fetchAvailableChecks();
+    fetchConditionChecks();
+    alert("Condition check submitted successfully!");
+  };
+
+  const getAvailableChecksForRental = (rentalId: string) => {
+    if (!Array.isArray(availableChecks)) return [];
+    return availableChecks.filter(
+      (check) =>
+        check.rentalId === rentalId && check.checkType === "pre_rental_owner" // Only pre-rental; post-rental is in return modal
+    );
+  };
+
+  const getCompletedChecksForRental = (rentalId: string) => {
+    if (!Array.isArray(conditionChecks)) return [];
+    return conditionChecks.filter(
+      (check) =>
+        check.rentalId === rentalId &&
+        (check.checkType === "pre_rental_owner" ||
+          check.checkType === "post_rental_owner")
+    );
+  };
+
  // Filter owner rentals
  const allOwnerRentals = ownerRentals
    .filter((r) =>
@@ -331,7 +432,8 @@ const MyListings: React.FC = () => {
                      </div>
                    )}

-                    <div className="d-flex gap-2 mt-3">
+                    <div className="d-flex flex-column gap-2 mt-3">
+                      <div className="d-flex gap-2">
                        {rental.status === "pending" && (
                          <>
                            <button
@@ -399,6 +501,47 @@ const MyListings: React.FC = () => {
                          </button>
                        )}
                      </div>
+
+                      {/* Condition Check Status */}
+                      {getCompletedChecksForRental(rental.id).length > 0 && (
+                        <div className="mb-2">
+                          {getCompletedChecksForRental(rental.id).map(
+                            (check) => (
+                              <div
+                                key={`${rental.id}-${check.checkType}-status`}
+                                className="text-success small"
+                              >
+                                <i className="bi bi-camera-fill me-1"></i>
+                                {check.checkType === "pre_rental_owner"
+                                  ? "Pre-Rental Check Completed"
+                                  : "Post-Rental Check Completed"}
+                                <small className="text-muted ms-2">
+                                  {new Date(
+                                    check.createdAt
+                                  ).toLocaleDateString()}
+                                </small>
+                              </div>
+                            )
+                          )}
+                        </div>
+                      )}
+
+                      {/* Condition Check Buttons */}
+                      {getAvailableChecksForRental(rental.id).map((check) => (
+                        <button
+                          key={`${rental.id}-${check.checkType}`}
+                          className="btn btn-sm btn-outline-primary"
+                          onClick={() =>
+                            handleConditionCheck(rental, check.checkType)
+                          }
+                        >
+                          <i className="bi bi-camera me-2" />
+                          {check.checkType === "pre_rental_owner"
+                            ? "Submit Pre-Rental Check"
+                            : "Submit Post-Rental Check"}
+                        </button>
+                      ))}
+                    </div>
                  </div>
                </div>
              </div>
@@ -572,6 +715,35 @@ const MyListings: React.FC = () => {
          onCancellationComplete={handleCancellationComplete}
        />
      )}
+
+      {/* Condition Check Modal */}
+      {conditionCheckData && (
+        <ConditionCheckModal
+          show={showConditionCheckModal}
+          onHide={() => {
+            setShowConditionCheckModal(false);
+            setConditionCheckData(null);
+          }}
+          rentalId={conditionCheckData.rental.id}
+          checkType={conditionCheckData.checkType}
+          itemName={conditionCheckData.rental.item?.name || "Item"}
+          onSuccess={handleConditionCheckSuccess}
+        />
+      )}
+
+      {/* Return Status Modal */}
+      {rentalForReturn && (
+        <ReturnStatusModal
+          show={showReturnStatusModal}
+          onHide={() => {
+            setShowReturnStatusModal(false);
+            setRentalForReturn(null);
+          }}
+          rental={rentalForReturn}
+          onReturnMarked={handleReturnStatusMarked}
+          onSubmitSuccess={handleReturnStatusMarked}
+        />
+      )}
    </div>
  );
 };
--- a/frontend/src/pages/MyRentals.tsx
+++ b/frontend/src/pages/MyRentals.tsx
@@ -1,10 +1,11 @@
 import React, { useState, useEffect } from "react";
 import { Link } from "react-router-dom";
 import { useAuth } from "../contexts/AuthContext";
-import { rentalAPI } from "../services/api";
+import { rentalAPI, conditionCheckAPI } from "../services/api";
 import { Rental } from "../types";
 import ReviewItemModal from "../components/ReviewModal";
 import RentalCancellationModal from "../components/RentalCancellationModal";
+import ConditionCheckModal from "../components/ConditionCheckModal";

 const MyRentals: React.FC = () => {
  // Helper function to format time
@@ -21,6 +22,21 @@ const MyRentals: React.FC = () => {
    }
  };

+  // Helper function to format date and time together
+  const formatDateTime = (dateTimeString: string) => {
+    const date = new Date(dateTimeString);
+    return date
+      .toLocaleDateString("en-US", {
+        month: "2-digit",
+        day: "2-digit",
+        year: "numeric",
+        hour: "numeric",
+        minute: "2-digit",
+        hour12: true,
+      })
+      .replace(",", "");
+  };
+
  const { user } = useAuth();
  const [rentals, setRentals] = useState<Rental[]>([]);
  const [loading, setLoading] = useState(true);
@@ -29,11 +45,25 @@ const MyRentals: React.FC = () => {
  const [selectedRental, setSelectedRental] = useState<Rental | null>(null);
  const [showCancelModal, setShowCancelModal] = useState(false);
  const [rentalToCancel, setRentalToCancel] = useState<Rental | null>(null);
+  const [showConditionCheckModal, setShowConditionCheckModal] = useState(false);
+  const [conditionCheckData, setConditionCheckData] = useState<{
+    rental: Rental;
+    checkType: string;
+  } | null>(null);
+  const [availableChecks, setAvailableChecks] = useState<any[]>([]);
+  const [conditionChecks, setConditionChecks] = useState<any[]>([]);

  useEffect(() => {
    fetchRentals();
+    fetchAvailableChecks();
  }, []);

+  useEffect(() => {
+    if (rentals.length > 0) {
+      fetchConditionChecks();
+    }
+  }, [rentals]);
+
  const fetchRentals = async () => {
    try {
      const response = await rentalAPI.getMyRentals();
@@ -45,6 +75,44 @@ const MyRentals: React.FC = () => {
    }
  };

+  const fetchAvailableChecks = async () => {
+    try {
+      const response = await conditionCheckAPI.getAvailableChecks();
+      const checks = Array.isArray(response.data.availableChecks)
+        ? response.data.availableChecks
+        : [];
+      setAvailableChecks(checks);
+    } catch (err: any) {
+      console.error("Failed to fetch available checks:", err);
+      setAvailableChecks([]);
+    }
+  };
+
+  const fetchConditionChecks = async () => {
+    try {
+      // Fetch condition checks for all rentals
+      const allChecks: any[] = [];
+      for (const rental of rentals) {
+        try {
+          const response = await conditionCheckAPI.getConditionChecks(
+            rental.id
+          );
+          const checks = Array.isArray(response.data.conditionChecks)
+            ? response.data.conditionChecks
+            : [];
+          allChecks.push(...checks);
+        } catch (err) {
+          // Continue even if one rental fails
+          console.error(`Failed to fetch checks for rental ${rental.id}:`, err);
+        }
+      }
+      setConditionChecks(allChecks);
+    } catch (err: any) {
+      console.error("Failed to fetch condition checks:", err);
+      setConditionChecks([]);
+    }
+  };
+
  const handleCancelClick = (rental: Rental) => {
    setRentalToCancel(rental);
    setShowCancelModal(true);
@@ -71,6 +139,37 @@ const MyRentals: React.FC = () => {
    alert("Thank you for your review!");
  };

+  const handleConditionCheck = (rental: Rental, checkType: string) => {
+    setConditionCheckData({ rental, checkType });
+    setShowConditionCheckModal(true);
+  };
+
+  const handleConditionCheckSuccess = () => {
+    fetchAvailableChecks();
+    fetchConditionChecks();
+    alert("Condition check submitted successfully!");
+  };
+
+  const getAvailableChecksForRental = (rentalId: string) => {
+    if (!Array.isArray(availableChecks)) return [];
+    return availableChecks.filter(
+      (check) =>
+        check.rentalId === rentalId &&
+        (check.checkType === "rental_start_renter" ||
+          check.checkType === "rental_end_renter")
+    );
+  };
+
+  const getCompletedChecksForRental = (rentalId: string) => {
+    if (!Array.isArray(conditionChecks)) return [];
+    return conditionChecks.filter(
+      (check) =>
+        check.rentalId === rentalId &&
+        (check.checkType === "rental_start_renter" ||
+          check.checkType === "rental_end_renter")
+    );
+  };
+
  // Filter rentals - only show active rentals (pending, confirmed, active)
  const renterActiveRentals = rentals.filter((r) =>
    ["pending", "confirmed", "active"].includes(r.status)
@@ -164,21 +263,13 @@ const MyRentals: React.FC = () => {
                      </span>
                    </div>

-                    {rental.status === "pending" && (
-                      <div className="alert alert-info mt-2 mb-2 p-2 small">
-                        You'll only be charged if the owner approves your
-                        request.
-                      </div>
-                    )}
-
                    <p className="mb-1 text-dark">
                      <strong>Rental Period:</strong>
                      <br />
                      <strong>Start:</strong>{" "}
-                      {new Date(rental.startDateTime).toLocaleString()}
+                      {formatDateTime(rental.startDateTime)}
                      <br />
-                      <strong>End:</strong>{" "}
-                      {new Date(rental.endDateTime).toLocaleString()}
+                      <strong>End:</strong> {formatDateTime(rental.endDateTime)}
                    </p>

                    <p className="mb-1 text-dark">
@@ -237,7 +328,8 @@ const MyRentals: React.FC = () => {
                      </>
                    )}

-                    <div className="d-flex gap-2 mt-3">
+                    <div className="d-flex flex-column gap-2 mt-3">
+                      <div className="d-flex gap-2">
                        {(rental.status === "pending" ||
                          rental.status === "confirmed") && (
                          <button
@@ -257,6 +349,49 @@ const MyRentals: React.FC = () => {
                              Review
                            </button>
                          )}
+                      </div>
+
+                      {/* Condition Check Status */}
+                      {getCompletedChecksForRental(rental.id).length > 0 && (
+                        <div className="mb-2">
+                          {getCompletedChecksForRental(rental.id).map(
+                            (check) => (
+                              <div
+                                key={`${rental.id}-${check.checkType}-status`}
+                                className="text-success small"
+                              >
+                                <i className="bi bi-camera-fill me-1"></i>
+                                {check.checkType === "rental_start_renter"
+                                  ? "Start Check Completed"
+                                  : "End Check Completed"}
+                                <small className="text-muted ms-2">
+                                  {new Date(
+                                    check.createdAt
+                                  ).toLocaleDateString()}
+                                </small>
+                              </div>
+                            )
+                          )}
+                        </div>
+                      )}
+
+                      {/* Condition Check Buttons */}
+                      {getAvailableChecksForRental(rental.id).map((check) => (
+                        <button
+                          key={`${rental.id}-${check.checkType}`}
+                          className="btn btn-sm btn-outline-primary"
+                          onClick={() =>
+                            handleConditionCheck(rental, check.checkType)
+                          }
+                        >
+                          <i className="bi bi-camera me-2" />
+                          {check.checkType === "rental_start_renter"
+                            ? "Submit Start Check"
+                            : "Submit End Check"}
+                        </button>
+                      ))}
+
+                      {/* Review Status */}
                      {rental.itemReviewSubmittedAt &&
                        !rental.itemReviewVisible && (
                          <div className="text-info small">
@@ -311,6 +446,21 @@ const MyRentals: React.FC = () => {
          onCancellationComplete={handleCancellationComplete}
        />
      )}
+
+      {/* Condition Check Modal */}
+      {conditionCheckData && (
+        <ConditionCheckModal
+          show={showConditionCheckModal}
+          onHide={() => {
+            setShowConditionCheckModal(false);
+            setConditionCheckData(null);
+          }}
+          rentalId={conditionCheckData.rental.id}
+          checkType={conditionCheckData.checkType}
+          itemName={conditionCheckData.rental.item?.name || "Item"}
+          onSuccess={handleConditionCheckSuccess}
+        />
+      )}
    </div>
  );
 };
--- a/frontend/src/services/api.ts
+++ b/frontend/src/services/api.ts
@@ -52,18 +52,6 @@ export const resetCSRFToken = () => {
  csrfToken = null;
 };

-// Check if authentication cookie exists
-export const hasAuthCookie = (): boolean => {
-  return document.cookie
-    .split("; ")
-    .some((cookie) => cookie.startsWith("accessToken="));
-};
-
-// Check if user has any auth indicators
-export const hasAuthIndicators = (): boolean => {
-  return hasAuthCookie();
-};
-
 api.interceptors.request.use(async (config) => {
  // Add CSRF token to headers for state-changing requests
  const method = config.method?.toUpperCase() || "";
@@ -119,14 +107,14 @@ api.interceptors.response.use(
    if (error.response?.status === 401) {
      const errorData = error.response?.data as any;

-      // Don't redirect for NO_TOKEN on public endpoints
-      if (errorData?.code === "NO_TOKEN") {
-        // Let the app handle this - user simply isn't logged in
-        return Promise.reject(error);
-      }
-
-      // If token is expired, try to refresh
-      if (errorData?.code === "TOKEN_EXPIRED" && !originalRequest._retry) {
+      // Try to refresh for token errors
+      // Note: We can't check refresh token from JS (httpOnly cookies)
+      // The backend will determine if refresh is possible
+      if (
+        (errorData?.code === "TOKEN_EXPIRED" ||
+          errorData?.code === "NO_TOKEN") &&
+        !originalRequest._retry
+      ) {
        if (isRefreshing) {
          // If already refreshing, queue the request
          return new Promise((resolve, reject) => {
@@ -152,18 +140,10 @@ api.interceptors.response.use(
          isRefreshing = false;
          processQueue(refreshError as AxiosError);

-          // Refresh failed, redirect to login
-          window.location.href = "/login";
+          // Refresh failed - let React Router handle redirects via PrivateRoute
          return Promise.reject(refreshError);
        }
      }
-
-      // For other 401 errors, check if we should redirect
-      // Only redirect if this is not a login/register request
-      const isAuthEndpoint = originalRequest.url?.includes("/auth/");
-      if (!isAuthEndpoint && errorData?.error !== "Access token required") {
-        window.location.href = "/login";
-      }
    }

    return Promise.reject(error);
@@ -223,8 +203,19 @@ export const rentalAPI = {
  reviewItem: (id: string, data: any) =>
    api.post(`/rentals/${id}/review-item`, data),
  getRefundPreview: (id: string) => api.get(`/rentals/${id}/refund-preview`),
+  getLateFeePreview: (id: string, actualReturnDateTime: string) =>
+    api.get(`/rentals/${id}/late-fee-preview`, {
+      params: { actualReturnDateTime },
+    }),
  cancelRental: (id: string, reason?: string) =>
    api.post(`/rentals/${id}/cancel`, { reason }),
+  // Return status marking
+  markReturn: (
+    id: string,
+    data: { status: string; actualReturnDateTime?: string; notes?: string }
+  ) => api.post(`/rentals/${id}/mark-return`, data),
+  reportDamage: (id: string, data: any) =>
+    api.post(`/rentals/${id}/report-damage`, data),
 };

 export const messageAPI = {
@@ -277,4 +268,35 @@ export const mapsAPI = {
  getHealth: () => api.get("/maps/health"),
 };

+export const conditionCheckAPI = {
+  submitConditionCheck: (rentalId: string, formData: FormData) =>
+    api.post(`/condition-checks/${rentalId}`, formData, {
+      headers: { "Content-Type": "multipart/form-data" },
+    }),
+  getConditionChecks: (rentalId: string) =>
+    api.get(`/condition-checks/${rentalId}`),
+  getConditionCheckTimeline: (rentalId: string) =>
+    api.get(`/condition-checks/${rentalId}/timeline`),
+  getAvailableChecks: () => api.get("/condition-checks"),
+};
+
+export const notificationAPI = {
+  getNotifications: (params?: { limit?: number; page?: number }) =>
+    api.get("/notifications", { params }),
+  getUnreadCount: () => api.get("/notifications/unread-count"),
+  markAsRead: (notificationId: string) =>
+    api.patch(`/notifications/${notificationId}/read`),
+  markAllAsRead: () => api.patch("/notifications/mark-all-read"),
+  // Development endpoints
+  createTestNotification: (data: {
+    type?: string;
+    title: string;
+    message: string;
+    metadata?: any;
+  }) => api.post("/notifications/test", data),
+  triggerConditionReminders: () =>
+    api.post("/notifications/test/condition-reminders"),
+  cleanupExpired: () => api.post("/notifications/test/cleanup-expired"),
+};
+
 export default api;
--- a/frontend/src/types/index.ts
+++ b/frontend/src/types/index.ts
@@ -107,7 +107,15 @@ export interface Rental {
  // Fee tracking fields
  platformFee?: number;
  payoutAmount?: number;
-  status: "pending" | "confirmed" | "active" | "completed" | "cancelled";
+  status:
+    | "pending"
+    | "confirmed"
+    | "active"
+    | "completed"
+    | "cancelled"
+    | "returned_late"
+    | "damaged"
+    | "lost";
  paymentStatus: "pending" | "paid" | "refunded";
  // Refund tracking fields
  refundAmount?: number;
@@ -140,6 +148,13 @@ export interface Rental {
  // Private messages
  itemPrivateMessage?: string;
  renterPrivateMessage?: string;
+  // New condition check and dispute fields
+  actualReturnDateTime?: string;
+  lateFees?: number;
+  damageFees?: number;
+  replacementFees?: number;
+  itemLostReportedAt?: string;
+  damageAssessment?: any;
  item?: Item;
  renter?: User;
  owner?: User;
@@ -147,6 +162,82 @@ export interface Rental {
  updatedAt: string;
 }

+export interface ConditionCheck {
+  id: string;
+  rentalId: string;
+  checkType:
+    | "pre_rental_owner"
+    | "rental_start_renter"
+    | "rental_end_renter"
+    | "post_rental_owner";
+  photos: string[];
+  notes?: string;
+  submittedBy: string;
+  submittedAt: string;
+  metadata: any;
+  submittedByUser?: User;
+  createdAt: string;
+  updatedAt: string;
+}
+
+export interface LateReturnCalculation {
+  lateHours: number;
+  lateFee: number;
+  isLate: boolean;
+  gracePeriodUsed?: boolean;
+  billableHours?: number;
+  pricingType?: "hourly" | "daily";
+}
+
+export interface DamageAssessment {
+  description: string;
+  canBeFixed: boolean;
+  repairCost?: number;
+  needsReplacement: boolean;
+  replacementCost?: number;
+  proofOfOwnership?: string[];
+  photos?: string[];
+  assessedAt: string;
+  assessedBy: string;
+  feeCalculation: {
+    type: "repair" | "replacement" | "assessment";
+    amount: number;
+    originalCost?: number;
+    repairCost?: number;
+    percentage?: number;
+    baseAmount?: number;
+  };
+}
+
+export interface ConditionCheckTimeline {
+  rental: {
+    id: string;
+    startDateTime: string;
+    endDateTime: string;
+    status: string;
+  };
+  timeline: {
+    [key: string]: {
+      status:
+        | "completed"
+        | "available"
+        | "pending"
+        | "expired"
+        | "not_available";
+      submittedAt?: string;
+      submittedBy?: User;
+      photoCount?: number;
+      hasNotes?: boolean;
+      timeWindow?: {
+        start: string;
+        end: string;
+      };
+      availableFrom?: string;
+      availableUntil?: string;
+    };
+  };
+}
+
 export interface ItemRequest {
  id: string;
  title: string;