diff --git a/.gitignore b/.gitignore
index f4e61e4..6b11e04 100644
--- a/.gitignore
+++ b/.gitignore
@@ -24,6 +24,8 @@ npm-debug.log*
 yarn-debug.log*
 yarn-error.log*
 lerna-debug.log*
+*.log
+logs/
 
 # Editor directories and files
 .idea
diff --git a/backend/middleware/apiLogger.js b/backend/middleware/apiLogger.js
new file mode 100644
index 0000000..af0df5d
--- /dev/null
+++ b/backend/middleware/apiLogger.js
@@ -0,0 +1,53 @@
+const logger = require('../utils/logger');
+
+const apiLogger = (req, res, next) => {
+  const startTime = Date.now();
+  const reqLogger = logger.withRequestId(req.id);
+
+  const requestData = {
+    method: req.method,
+    url: req.url,
+    userAgent: req.get('User-Agent'),
+    ip: req.ip,
+    userId: req.user?.id || 'anonymous',
+    body: logger.sanitize(req.body),
+    params: req.params,
+    query: req.query,
+    headers: {
+      'content-type': req.get('Content-Type'),
+      'content-length': req.get('Content-Length'),
+      'referer': req.get('Referer'),
+    }
+  };
+
+  reqLogger.info('API Request', requestData);
+
+  const originalSend = res.send;
+  res.send = function(body) {
+    const endTime = Date.now();
+    const responseTime = endTime - startTime;
+
+    const responseData = {
+      statusCode: res.statusCode,
+      responseTime: `${responseTime}ms`,
+      contentLength: res.get('Content-Length') || (body ? body.length : 0),
+      method: req.method,
+      url: req.url,
+      userId: req.user?.id || 'anonymous'
+    };
+
+    if (res.statusCode >= 400 && res.statusCode < 500) {
+      reqLogger.warn('API Response - Client Error', responseData);
+    } else if (res.statusCode >= 500) {
+      reqLogger.error('API Response - Server Error', responseData);
+    } else {
+      reqLogger.info('API Response - Success', responseData);
+    }
+
+    return originalSend.call(this, body);
+  };
+
+  next();
+};
+
+module.exports = apiLogger;
\ No newline at end of file
diff --git a/backend/middleware/auth.js b/backend/middleware/auth.js
index 4f51c6c..f532b46 100644
--- a/backend/middleware/auth.js
+++ b/backend/middleware/auth.js
@@ -1,5 +1,6 @@
 const jwt = require("jsonwebtoken");
 const { User } = require("../models"); // Import from models/index.js to get models with associations
+const logger = require("../utils/logger");
 
 const authenticateToken = async (req, res, next) => {
   // First try to get token from cookie
@@ -43,7 +44,13 @@ const authenticateToken = async (req, res, next) => {
       });
     }
 
-    console.error("Auth middleware error:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Auth middleware error", {
+      error: error.message,
+      stack: error.stack,
+      tokenPresent: !!token,
+      userId: req.user?.id
+    });
     return res.status(403).json({
       error: "Invalid token",
       code: "INVALID_TOKEN",
diff --git a/backend/middleware/errorLogger.js b/backend/middleware/errorLogger.js
new file mode 100644
index 0000000..d9f81c1
--- /dev/null
+++ b/backend/middleware/errorLogger.js
@@ -0,0 +1,33 @@
+const logger = require('../utils/logger');
+
+const errorLogger = (err, req, res, next) => {
+  // Create a request-specific logger with request ID
+  const reqLogger = logger.withRequestId(req.id);
+
+  // Log the error with context
+  const errorContext = {
+    method: req.method,
+    url: req.url,
+    userAgent: req.get('User-Agent'),
+    ip: req.ip,
+    userId: req.user?.id || 'anonymous',
+    body: logger.sanitize(req.body),
+    params: req.params,
+    query: req.query,
+    statusCode: err.statusCode || 500,
+    stack: err.stack,
+  };
+
+  if (err.statusCode && err.statusCode < 500) {
+    // Client errors (4xx)
+    reqLogger.warn(`Client error: ${err.message}`, errorContext);
+  } else {
+    // Server errors (5xx)
+    reqLogger.error(`Server error: ${err.message}`, errorContext);
+  }
+
+  // Pass error to next middleware
+  next(err);
+};
+
+module.exports = errorLogger;
\ No newline at end of file
diff --git a/backend/middleware/security.js b/backend/middleware/security.js
index 4eb0d71..ec83a26 100644
--- a/backend/middleware/security.js
+++ b/backend/middleware/security.js
@@ -1,3 +1,5 @@
+const logger = require('../utils/logger');
+
 // HTTPS enforcement middleware
 const enforceHTTPS = (req, res, next) => {
   // Skip HTTPS enforcement in development
@@ -20,11 +22,13 @@ const enforceHTTPS = (req, res, next) => {
 
     // Log the redirect for monitoring
     if (req.headers.host !== allowedHost) {
-      console.warn("[SECURITY] Host header mismatch during HTTPS redirect:", {
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.warn("Host header mismatch during HTTPS redirect", {
         requestHost: req.headers.host,
         allowedHost,
         ip: req.ip,
         url: req.url,
+        eventType: 'SECURITY_HOST_MISMATCH'
       });
     }
 
@@ -70,34 +74,21 @@ const addRequestId = (req, res, next) => {
 
 // Log security events
 const logSecurityEvent = (eventType, details, req) => {
+  const reqLogger = logger.withRequestId(req.id || "unknown");
+
   const logEntry = {
-    timestamp: new Date().toISOString(),
     eventType,
-    requestId: req.id || "unknown",
     ip: req.ip || req.connection.remoteAddress,
     userAgent: req.get("user-agent"),
     userId: req.user?.id || "anonymous",
     ...details,
   };
 
-  // In production, this should write to a secure log file or service
-  if (process.env.NODE_ENV === "production") {
-    console.log("[SECURITY]", JSON.stringify(logEntry));
-  } else {
-    console.log("[SECURITY]", eventType, details);
-  }
+  reqLogger.warn(`Security event: ${eventType}`, logEntry);
 };
 
 // Sanitize error messages to prevent information leakage
 const sanitizeError = (err, req, res, next) => {
-  // Log the full error internally
-  console.error("Error:", {
-    requestId: req.id,
-    error: err.message,
-    stack: err.stack,
-    userId: req.user?.id,
-  });
-
   // Send sanitized error to client
   const isDevelopment =
     process.env.NODE_ENV === "dev" || process.env.NODE_ENV === "development";
diff --git a/backend/package-lock.json b/backend/package-lock.json
index 062c7ec..55f8061 100644
--- a/backend/package-lock.json
+++ b/backend/package-lock.json
@@ -24,13 +24,16 @@
         "helmet": "^8.1.0",
         "jsdom": "^27.0.0",
         "jsonwebtoken": "^9.0.2",
+        "morgan": "^1.10.1",
         "multer": "^2.0.2",
         "node-cron": "^3.0.3",
         "pg": "^8.16.3",
         "sequelize": "^6.37.7",
         "sequelize-cli": "^6.6.3",
         "stripe": "^18.4.0",
-        "uuid": "^11.1.0"
+        "uuid": "^11.1.0",
+        "winston": "^3.17.0",
+        "winston-daily-rotate-file": "^5.0.0"
       },
       "devDependencies": {
         "@types/jest": "^30.0.0",
@@ -607,6 +610,15 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@colors/colors": {
+      "version": "1.6.0",
+      "resolved": "https://registry.npmjs.org/@colors/colors/-/colors-1.6.0.tgz",
+      "integrity": "sha512-Ir+AOibqzrIsL6ajt3Rz3LskB7OiMVHqltZmspbW/TJuTVuyOMirVqAkjfY6JISiLHgyNqicAC8AyHHGzNd/dA==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.1.90"
+      }
+    },
     "node_modules/@csstools/color-helpers": {
       "version": "5.1.0",
       "resolved": "https://registry.npmjs.org/@csstools/color-helpers/-/color-helpers-5.1.0.tgz",
@@ -739,6 +751,17 @@
         "node": ">=18"
       }
     },
+    "node_modules/@dabh/diagnostics": {
+      "version": "2.0.3",
+      "resolved": "https://registry.npmjs.org/@dabh/diagnostics/-/diagnostics-2.0.3.tgz",
+      "integrity": "sha512-hrlQOIi7hAfzsMqlGSFyVucrx38O+j6wiGOf//H2ecvIEqYN4ADBSS2iLMh5UFyDunCNniUIPk/q3riFv45xRA==",
+      "license": "MIT",
+      "dependencies": {
+        "colorspace": "1.1.x",
+        "enabled": "2.0.x",
+        "kuler": "^2.0.0"
+      }
+    },
     "node_modules/@googlemaps/google-maps-services-js": {
       "version": "3.4.2",
       "resolved": "https://registry.npmjs.org/@googlemaps/google-maps-services-js/-/google-maps-services-js-3.4.2.tgz",
@@ -1405,6 +1428,12 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/triple-beam": {
+      "version": "1.3.5",
+      "resolved": "https://registry.npmjs.org/@types/triple-beam/-/triple-beam-1.3.5.tgz",
+      "integrity": "sha512-6WaYesThRMCl19iryMYP7/x2OVgCtbIVflDGFpWnb9irXI3UjYE4AzmYuiUKY1AJstGijoY+MgUszMgRxIYTYw==",
+      "license": "MIT"
+    },
     "node_modules/@types/trusted-types": {
       "version": "2.0.7",
       "resolved": "https://registry.npmjs.org/@types/trusted-types/-/trusted-types-2.0.7.tgz",
@@ -1570,6 +1599,12 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/async": {
+      "version": "3.2.6",
+      "resolved": "https://registry.npmjs.org/async/-/async-3.2.6.tgz",
+      "integrity": "sha512-htCUDlxyyCLMgaM3xXg0C0LW2xqfuQ6p05pCEIsXuyQ+a1koYKTuBMzRNwmybfLgvJDMd0r1LTn4+E0Ti6C2AA==",
+      "license": "MIT"
+    },
     "node_modules/asynckit": {
       "version": "0.4.0",
       "resolved": "https://registry.npmjs.org/asynckit/-/asynckit-0.4.0.tgz",
@@ -1731,6 +1766,24 @@
         "baseline-browser-mapping": "dist/cli.js"
       }
     },
+    "node_modules/basic-auth": {
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/basic-auth/-/basic-auth-2.0.1.tgz",
+      "integrity": "sha512-NF+epuEdnUYVlGuhaxbbq+dvJttwLnGY+YixlXlME5KpQ5W3CnXA5cVTneY3SPbPDRkcjMbifrwmFYcClgOZeg==",
+      "license": "MIT",
+      "dependencies": {
+        "safe-buffer": "5.1.2"
+      },
+      "engines": {
+        "node": ">= 0.8"
+      }
+    },
+    "node_modules/basic-auth/node_modules/safe-buffer": {
+      "version": "5.1.2",
+      "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.1.2.tgz",
+      "integrity": "sha512-Gd2UZBJDkXlY7GbJxfsE8/nvKkUEU1G38c1siN6QP6a9PT9MmHB8GnpscSmMJSoF8LOIrt8ud/wPtojys4G6+g==",
+      "license": "MIT"
+    },
     "node_modules/bcryptjs": {
       "version": "3.0.2",
       "resolved": "https://registry.npmjs.org/bcryptjs/-/bcryptjs-3.0.2.tgz",
@@ -2163,6 +2216,16 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/color": {
+      "version": "3.2.1",
+      "resolved": "https://registry.npmjs.org/color/-/color-3.2.1.tgz",
+      "integrity": "sha512-aBl7dZI9ENN6fUGC7mWpMTPNHmWUSNan9tuWN6ahh5ZLNk9baLJOnSMlrQkHcrfFgz2/RigjUVAjdx36VcemKA==",
+      "license": "MIT",
+      "dependencies": {
+        "color-convert": "^1.9.3",
+        "color-string": "^1.6.0"
+      }
+    },
     "node_modules/color-convert": {
       "version": "2.0.1",
       "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-2.0.1.tgz",
@@ -2179,6 +2242,41 @@
       "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.4.tgz",
       "integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA=="
     },
+    "node_modules/color-string": {
+      "version": "1.9.1",
+      "resolved": "https://registry.npmjs.org/color-string/-/color-string-1.9.1.tgz",
+      "integrity": "sha512-shrVawQFojnZv6xM40anx4CkoDP+fZsw/ZerEMsW/pyzsRbElpsL/DBVW7q3ExxwusdNXI3lXpuhEZkzs8p5Eg==",
+      "license": "MIT",
+      "dependencies": {
+        "color-name": "^1.0.0",
+        "simple-swizzle": "^0.2.2"
+      }
+    },
+    "node_modules/color/node_modules/color-convert": {
+      "version": "1.9.3",
+      "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-1.9.3.tgz",
+      "integrity": "sha512-QfAUtd+vFdAtFQcC8CCyYt1fYWxSqAiK2cSD6zDB8N3cpsEBAvRxp9zOGg6G/SHHJYAT88/az/IuDGALsNVbGg==",
+      "license": "MIT",
+      "dependencies": {
+        "color-name": "1.1.3"
+      }
+    },
+    "node_modules/color/node_modules/color-name": {
+      "version": "1.1.3",
+      "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.3.tgz",
+      "integrity": "sha512-72fSenhMw2HZMTVHeCA9KCmpEIbzWiQsjN+BHcBbS9vr1mtt+vJjPdksIBNUmKAW8TFUDPJK5SUU3QhE9NEXDw==",
+      "license": "MIT"
+    },
+    "node_modules/colorspace": {
+      "version": "1.1.4",
+      "resolved": "https://registry.npmjs.org/colorspace/-/colorspace-1.1.4.tgz",
+      "integrity": "sha512-BgvKJiuVu1igBUF2kEjRCZXol6wiiGbY5ipL/oVPwm0BL9sIpMIzM8IK7vwuxIIzOXMV3Ey5w+vxhm0rR/TN8w==",
+      "license": "MIT",
+      "dependencies": {
+        "color": "^3.1.3",
+        "text-hex": "1.0.x"
+      }
+    },
     "node_modules/combined-stream": {
       "version": "1.0.8",
       "resolved": "https://registry.npmjs.org/combined-stream/-/combined-stream-1.0.8.tgz",
@@ -2603,6 +2701,12 @@
       "resolved": "https://registry.npmjs.org/emoji-regex/-/emoji-regex-9.2.2.tgz",
       "integrity": "sha512-L18DaJsXSUk2+42pv8mLs5jJT2hqFkFE4j21wOmgbUqsZ2hL72NsUU785g9RXgo3s0ZNgVl42TiHp3ZtOv/Vyg=="
     },
+    "node_modules/enabled": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/enabled/-/enabled-2.0.0.tgz",
+      "integrity": "sha512-AKrN98kuwOzMIdAizXGI86UFBoo26CL21UM763y1h/GMSJ4/OHU9k2YlsmBpyScFo/wbLzWQJBMCW4+IO3/+OQ==",
+      "license": "MIT"
+    },
     "node_modules/encodeurl": {
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/encodeurl/-/encodeurl-2.0.0.tgz",
@@ -2897,6 +3001,12 @@
         "bser": "2.1.1"
       }
     },
+    "node_modules/fecha": {
+      "version": "4.2.3",
+      "resolved": "https://registry.npmjs.org/fecha/-/fecha-4.2.3.tgz",
+      "integrity": "sha512-OP2IUU6HeYKJi3i0z4A19kHMQoLVs4Hc+DPqqxI2h/DPZHTm/vjsfC6P0b4jCMy14XizLBqvndQ+UilD7707Jw==",
+      "license": "MIT"
+    },
     "node_modules/fetch-blob": {
       "version": "3.2.0",
       "resolved": "https://registry.npmjs.org/fetch-blob/-/fetch-blob-3.2.0.tgz",
@@ -2920,6 +3030,15 @@
         "node": "^12.20 || >= 14.13"
       }
     },
+    "node_modules/file-stream-rotator": {
+      "version": "0.6.1",
+      "resolved": "https://registry.npmjs.org/file-stream-rotator/-/file-stream-rotator-0.6.1.tgz",
+      "integrity": "sha512-u+dBid4PvZw17PmDeRcNOtCP9CCK/9lRN2w+r1xIS7yOL9JFrIBKTvrYsxT4P0pGtThYTn++QS5ChHaUov3+zQ==",
+      "license": "MIT",
+      "dependencies": {
+        "moment": "^2.29.1"
+      }
+    },
     "node_modules/fill-range": {
       "version": "7.1.1",
       "resolved": "https://registry.npmjs.org/fill-range/-/fill-range-7.1.1.tgz",
@@ -2971,6 +3090,12 @@
         "node": ">=8"
       }
     },
+    "node_modules/fn.name": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/fn.name/-/fn.name-1.1.0.tgz",
+      "integrity": "sha512-GRnmB5gPyJpAhTQdSZTSp9uaPSvl09KoYcMQtsB9rQoOmzs9dH6ffeccH+Z+cv6P68Hu5bC6JjRh4Ah/mHSNRw==",
+      "license": "MIT"
+    },
     "node_modules/follow-redirects": {
       "version": "1.15.11",
       "resolved": "https://registry.npmjs.org/follow-redirects/-/follow-redirects-1.15.11.tgz",
@@ -3615,6 +3740,12 @@
         "node": ">= 0.10"
       }
     },
+    "node_modules/is-arrayish": {
+      "version": "0.3.4",
+      "resolved": "https://registry.npmjs.org/is-arrayish/-/is-arrayish-0.3.4.tgz",
+      "integrity": "sha512-m6UrgzFVUYawGBh1dUsWR5M2Clqic9RVXC/9f8ceNlv2IcO9j9J/z8UoCLPqtsPBFNzEpfR3xftohbfqDx8EQA==",
+      "license": "MIT"
+    },
     "node_modules/is-binary-path": {
       "version": "2.1.0",
       "resolved": "https://registry.npmjs.org/is-binary-path/-/is-binary-path-2.1.0.tgz",
@@ -3704,7 +3835,6 @@
       "version": "2.0.1",
       "resolved": "https://registry.npmjs.org/is-stream/-/is-stream-2.0.1.tgz",
       "integrity": "sha512-hFoiJiTl63nn+kstHGBtewWSKnQLpyb155KHheA1l39uvtO9nWIop1p3udqPcUd/xbF1VLMO4n7OI6p7RbngDg==",
-      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">=8"
@@ -4733,6 +4863,12 @@
         "safe-buffer": "^5.0.1"
       }
     },
+    "node_modules/kuler": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/kuler/-/kuler-2.0.0.tgz",
+      "integrity": "sha512-Xq9nH7KlWZmXAtodXDDRE7vs6DU1gTU8zYDHDiWLSip45Egwq3plLHzPn27NgvzL2r1LMPC1vdqh98sQxtqj4A==",
+      "license": "MIT"
+    },
     "node_modules/leven": {
       "version": "3.1.0",
       "resolved": "https://registry.npmjs.org/leven/-/leven-3.1.0.tgz",
@@ -4803,6 +4939,23 @@
       "resolved": "https://registry.npmjs.org/lodash.once/-/lodash.once-4.1.1.tgz",
       "integrity": "sha512-Sb487aTOCr9drQVL8pIxOzVhafOjZN9UU54hiN8PU3uAiSV7lx1yYNpbNmex2PK6dSJoNTSJUUswT651yww3Mg=="
     },
+    "node_modules/logform": {
+      "version": "2.7.0",
+      "resolved": "https://registry.npmjs.org/logform/-/logform-2.7.0.tgz",
+      "integrity": "sha512-TFYA4jnP7PVbmlBIfhlSe+WKxs9dklXMTEGcBCIvLhE/Tn3H6Gk1norupVW7m5Cnd4bLcr08AytbyV/xj7f/kQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@colors/colors": "1.6.0",
+        "@types/triple-beam": "^1.3.2",
+        "fecha": "^4.2.0",
+        "ms": "^2.1.1",
+        "safe-stable-stringify": "^2.3.1",
+        "triple-beam": "^1.3.0"
+      },
+      "engines": {
+        "node": ">= 12.0.0"
+      }
+    },
     "node_modules/lru-cache": {
       "version": "10.4.3",
       "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-10.4.3.tgz",
@@ -5002,6 +5155,49 @@
         "node": "*"
       }
     },
+    "node_modules/morgan": {
+      "version": "1.10.1",
+      "resolved": "https://registry.npmjs.org/morgan/-/morgan-1.10.1.tgz",
+      "integrity": "sha512-223dMRJtI/l25dJKWpgij2cMtywuG/WiUKXdvwfbhGKBhy1puASqXwFzmWZ7+K73vUPoR7SS2Qz2cI/g9MKw0A==",
+      "license": "MIT",
+      "dependencies": {
+        "basic-auth": "~2.0.1",
+        "debug": "2.6.9",
+        "depd": "~2.0.0",
+        "on-finished": "~2.3.0",
+        "on-headers": "~1.1.0"
+      },
+      "engines": {
+        "node": ">= 0.8.0"
+      }
+    },
+    "node_modules/morgan/node_modules/debug": {
+      "version": "2.6.9",
+      "resolved": "https://registry.npmjs.org/debug/-/debug-2.6.9.tgz",
+      "integrity": "sha512-bC7ElrdJaJnPbAP+1EotYvqZsb3ecl5wi6Bfi6BJTUcNowp6cvspg0jXznRTKDjm/E7AdgFBVeAPVMNcKGsHMA==",
+      "license": "MIT",
+      "dependencies": {
+        "ms": "2.0.0"
+      }
+    },
+    "node_modules/morgan/node_modules/ms": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/ms/-/ms-2.0.0.tgz",
+      "integrity": "sha512-Tpp60P6IUJDTuOq/5Z8cdskzJujfwqfOTkrwIwj7IRISpnkJnT6SyJ4PCPnGMoFjC9ddhal5KVIYtAt97ix05A==",
+      "license": "MIT"
+    },
+    "node_modules/morgan/node_modules/on-finished": {
+      "version": "2.3.0",
+      "resolved": "https://registry.npmjs.org/on-finished/-/on-finished-2.3.0.tgz",
+      "integrity": "sha512-ikqdkGAAyf/X/gPhXGvfgAytDZtDbr+bkNUJ0N9h5MI/dmdgCs3l6hoHrcUv41sRKew3jIwrp4qQDXiK99Utww==",
+      "license": "MIT",
+      "dependencies": {
+        "ee-first": "1.1.1"
+      },
+      "engines": {
+        "node": ">= 0.8"
+      }
+    },
     "node_modules/ms": {
       "version": "2.1.3",
       "resolved": "https://registry.npmjs.org/ms/-/ms-2.1.3.tgz",
@@ -5285,6 +5481,15 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/object-hash": {
+      "version": "3.0.0",
+      "resolved": "https://registry.npmjs.org/object-hash/-/object-hash-3.0.0.tgz",
+      "integrity": "sha512-RSn9F68PjH9HqtltsSnqYC1XXoWe9Bju5+213R98cNGttag9q9yAOTzdbsqvIa7aNm5WffBZFpWYr2aWrklWAw==",
+      "license": "MIT",
+      "engines": {
+        "node": ">= 6"
+      }
+    },
     "node_modules/object-inspect": {
       "version": "1.13.4",
       "resolved": "https://registry.npmjs.org/object-inspect/-/object-inspect-1.13.4.tgz",
@@ -5307,6 +5512,15 @@
         "node": ">= 0.8"
       }
     },
+    "node_modules/on-headers": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/on-headers/-/on-headers-1.1.0.tgz",
+      "integrity": "sha512-737ZY3yNnXy37FHkQxPzt4UZ2UWPWiCZWLvFZ4fu5cueciegX0zGPnrlY6bwRg4FdQOe9YU8MkmJwGhoMybl8A==",
+      "license": "MIT",
+      "engines": {
+        "node": ">= 0.8"
+      }
+    },
     "node_modules/once": {
       "version": "1.4.0",
       "resolved": "https://registry.npmjs.org/once/-/once-1.4.0.tgz",
@@ -5315,6 +5529,15 @@
         "wrappy": "1"
       }
     },
+    "node_modules/one-time": {
+      "version": "1.0.0",
+      "resolved": "https://registry.npmjs.org/one-time/-/one-time-1.0.0.tgz",
+      "integrity": "sha512-5DXOiRKwuSEcQ/l0kGCF6Q3jcADFv5tSmRaJck/OqkVFcOzutB134KRSfF0xDrL39MNnqxbHBbUUcjZIhTgb2g==",
+      "license": "MIT",
+      "dependencies": {
+        "fn.name": "1.x.x"
+      }
+    },
     "node_modules/onetime": {
       "version": "5.1.2",
       "resolved": "https://registry.npmjs.org/onetime/-/onetime-5.1.2.tgz",
@@ -5972,6 +6195,15 @@
         }
       ]
     },
+    "node_modules/safe-stable-stringify": {
+      "version": "2.5.0",
+      "resolved": "https://registry.npmjs.org/safe-stable-stringify/-/safe-stable-stringify-2.5.0.tgz",
+      "integrity": "sha512-b3rppTKm9T+PsVCBEOUR46GWI7fdOs00VKZ1+9c1EWDaDMvjQc6tUwuFyIprgGgTcWoVHSKrU8H31ZHA2e0RHA==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=10"
+      }
+    },
     "node_modules/safer-buffer": {
       "version": "2.1.2",
       "resolved": "https://registry.npmjs.org/safer-buffer/-/safer-buffer-2.1.2.tgz",
@@ -6249,6 +6481,15 @@
         "url": "https://github.com/sponsors/isaacs"
       }
     },
+    "node_modules/simple-swizzle": {
+      "version": "0.2.4",
+      "resolved": "https://registry.npmjs.org/simple-swizzle/-/simple-swizzle-0.2.4.tgz",
+      "integrity": "sha512-nAu1WFPQSMNr2Zn9PGSZK9AGn4t/y97lEm+MXTtUDwfP0ksAIX4nO+6ruD9Jwut4C49SB1Ws+fbXsm/yScWOHw==",
+      "license": "MIT",
+      "dependencies": {
+        "is-arrayish": "^0.3.1"
+      }
+    },
     "node_modules/simple-update-notifier": {
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/simple-update-notifier/-/simple-update-notifier-2.0.0.tgz",
@@ -6366,6 +6607,15 @@
       "dev": true,
       "license": "BSD-3-Clause"
     },
+    "node_modules/stack-trace": {
+      "version": "0.0.10",
+      "resolved": "https://registry.npmjs.org/stack-trace/-/stack-trace-0.0.10.tgz",
+      "integrity": "sha512-KGzahc7puUKkzyMt+IqAep+TVNbKP+k2Lmwhub39m1AsTSkaDutx56aDCo+HLDzf/D26BIHTJWNiTG1KAJiQCg==",
+      "license": "MIT",
+      "engines": {
+        "node": "*"
+      }
+    },
     "node_modules/stack-utils": {
       "version": "2.0.6",
       "resolved": "https://registry.npmjs.org/stack-utils/-/stack-utils-2.0.6.tgz",
@@ -6732,6 +6982,12 @@
         "node": "*"
       }
     },
+    "node_modules/text-hex": {
+      "version": "1.0.0",
+      "resolved": "https://registry.npmjs.org/text-hex/-/text-hex-1.0.0.tgz",
+      "integrity": "sha512-uuVGNWzgJ4yhRaNSiubPY7OjISw4sw4E5Uv0wbjp+OzcbmVU/rsT8ujgcXJhn9ypzsgr5vlzpPqP+MBBKcGvbg==",
+      "license": "MIT"
+    },
     "node_modules/tldts": {
       "version": "7.0.14",
       "resolved": "https://registry.npmjs.org/tldts/-/tldts-7.0.14.tgz",
@@ -6815,6 +7071,15 @@
         "node": ">=18"
       }
     },
+    "node_modules/triple-beam": {
+      "version": "1.4.1",
+      "resolved": "https://registry.npmjs.org/triple-beam/-/triple-beam-1.4.1.tgz",
+      "integrity": "sha512-aZbgViZrg1QNcG+LULa7nhZpJTZSLm/mXnHXnbAbjmN5aSa0y7V+wvv6+4WaBtpISJzThKy+PIPxc1Nq1EJ9mg==",
+      "license": "MIT",
+      "engines": {
+        "node": ">= 14.0.0"
+      }
+    },
     "node_modules/tsscmp": {
       "version": "1.0.6",
       "resolved": "https://registry.npmjs.org/tsscmp/-/tsscmp-1.0.6.tgz",
@@ -7120,6 +7385,60 @@
         "node": ">= 8"
       }
     },
+    "node_modules/winston": {
+      "version": "3.17.0",
+      "resolved": "https://registry.npmjs.org/winston/-/winston-3.17.0.tgz",
+      "integrity": "sha512-DLiFIXYC5fMPxaRg832S6F5mJYvePtmO5G9v9IgUFPhXm9/GkXarH/TUrBAVzhTCzAj9anE/+GjrgXp/54nOgw==",
+      "license": "MIT",
+      "dependencies": {
+        "@colors/colors": "^1.6.0",
+        "@dabh/diagnostics": "^2.0.2",
+        "async": "^3.2.3",
+        "is-stream": "^2.0.0",
+        "logform": "^2.7.0",
+        "one-time": "^1.0.0",
+        "readable-stream": "^3.4.0",
+        "safe-stable-stringify": "^2.3.1",
+        "stack-trace": "0.0.x",
+        "triple-beam": "^1.3.0",
+        "winston-transport": "^4.9.0"
+      },
+      "engines": {
+        "node": ">= 12.0.0"
+      }
+    },
+    "node_modules/winston-daily-rotate-file": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/winston-daily-rotate-file/-/winston-daily-rotate-file-5.0.0.tgz",
+      "integrity": "sha512-JDjiXXkM5qvwY06733vf09I2wnMXpZEhxEVOSPenZMii+g7pcDcTBt2MRugnoi8BwVSuCT2jfRXBUy+n1Zz/Yw==",
+      "license": "MIT",
+      "dependencies": {
+        "file-stream-rotator": "^0.6.1",
+        "object-hash": "^3.0.0",
+        "triple-beam": "^1.4.1",
+        "winston-transport": "^4.7.0"
+      },
+      "engines": {
+        "node": ">=8"
+      },
+      "peerDependencies": {
+        "winston": "^3"
+      }
+    },
+    "node_modules/winston-transport": {
+      "version": "4.9.0",
+      "resolved": "https://registry.npmjs.org/winston-transport/-/winston-transport-4.9.0.tgz",
+      "integrity": "sha512-8drMJ4rkgaPo1Me4zD/3WLfI/zPdA9o2IipKODunnGDcuqbHwjsbB79ylv04LCGGzU0xQ6vTznOMpQGaLhhm6A==",
+      "license": "MIT",
+      "dependencies": {
+        "logform": "^2.7.0",
+        "readable-stream": "^3.6.2",
+        "triple-beam": "^1.3.0"
+      },
+      "engines": {
+        "node": ">= 12.0.0"
+      }
+    },
     "node_modules/wkx": {
       "version": "0.5.0",
       "resolved": "https://registry.npmjs.org/wkx/-/wkx-0.5.0.tgz",
diff --git a/backend/package.json b/backend/package.json
index 486811a..c091d76 100644
--- a/backend/package.json
+++ b/backend/package.json
@@ -36,13 +36,16 @@
     "helmet": "^8.1.0",
     "jsdom": "^27.0.0",
     "jsonwebtoken": "^9.0.2",
+    "morgan": "^1.10.1",
     "multer": "^2.0.2",
     "node-cron": "^3.0.3",
     "pg": "^8.16.3",
     "sequelize": "^6.37.7",
     "sequelize-cli": "^6.6.3",
     "stripe": "^18.4.0",
-    "uuid": "^11.1.0"
+    "uuid": "^11.1.0",
+    "winston": "^3.17.0",
+    "winston-daily-rotate-file": "^5.0.0"
   },
   "devDependencies": {
     "@types/jest": "^30.0.0",
diff --git a/backend/routes/auth.js b/backend/routes/auth.js
index 4d77e08..358abcf 100644
--- a/backend/routes/auth.js
+++ b/backend/routes/auth.js
@@ -2,6 +2,7 @@ const express = require("express");
 const jwt = require("jsonwebtoken");
 const { OAuth2Client } = require("google-auth-library");
 const { User } = require("../models"); // Import from models/index.js to get models with associations
+const logger = require("../utils/logger");
 const {
   sanitizeInput,
   validateRegistration,
@@ -84,6 +85,13 @@ router.post(
         maxAge: 7 * 24 * 60 * 60 * 1000, // 7 days
       });
 
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("User registration successful", {
+        userId: user.id,
+        username: user.username,
+        email: user.email
+      });
+
       res.status(201).json({
         user: {
           id: user.id,
@@ -95,7 +103,13 @@ router.post(
         // Don't send token in response body for security
       });
     } catch (error) {
-      console.error("Registration error:", error);
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Registration error", {
+        error: error.message,
+        stack: error.stack,
+        email: req.body.email,
+        username: req.body.username
+      });
       res.status(500).json({ error: "Registration failed. Please try again." });
     }
   }
@@ -164,6 +178,12 @@ router.post(
         maxAge: 7 * 24 * 60 * 60 * 1000, // 7 days
       });
 
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("User login successful", {
+        userId: user.id,
+        email: user.email
+      });
+
       res.json({
         user: {
           id: user.id,
@@ -175,7 +195,12 @@ router.post(
         // Don't send token in response body for security
       });
     } catch (error) {
-      console.error("Login error:", error);
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Login error", {
+        error: error.message,
+        stack: error.stack,
+        email: req.body.email
+      });
       res.status(500).json({ error: "Login failed. Please try again." });
     }
   }
@@ -271,6 +296,13 @@ router.post(
         maxAge: 7 * 24 * 60 * 60 * 1000,
       });
 
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Google authentication successful", {
+        userId: user.id,
+        email: user.email,
+        isNewUser: !user.createdAt || (Date.now() - new Date(user.createdAt).getTime()) < 1000
+      });
+
       res.json({
         user: {
           id: user.id,
@@ -298,7 +330,12 @@ router.post(
           .status(400)
           .json({ error: "Malformed Google token. Please try again." });
       }
-      console.error("Google auth error:", error);
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Google auth error", {
+        error: error.message,
+        stack: error.stack,
+        tokenInfo: logger.sanitize({ idToken: req.body.idToken })
+      });
       res
         .status(500)
         .json({ error: "Google authentication failed. Please try again." });
@@ -341,6 +378,11 @@ router.post("/refresh", async (req, res) => {
       maxAge: 15 * 60 * 1000,
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Token refresh successful", {
+      userId: user.id
+    });
+
     res.json({
       user: {
         id: user.id,
@@ -351,13 +393,23 @@ router.post("/refresh", async (req, res) => {
       },
     });
   } catch (error) {
-    console.error("Token refresh error:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Token refresh error", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user?.id
+    });
     res.status(401).json({ error: "Invalid or expired refresh token" });
   }
 });
 
 // Logout endpoint
 router.post("/logout", (req, res) => {
+  const reqLogger = logger.withRequestId(req.id);
+  reqLogger.info("User logout", {
+    userId: req.user?.id || 'anonymous'
+  });
+
   // Clear cookies
   res.clearCookie("accessToken");
   res.clearCookie("refreshToken");
diff --git a/backend/routes/itemRequests.js b/backend/routes/itemRequests.js
index 4826d5b..d5af823 100644
--- a/backend/routes/itemRequests.js
+++ b/backend/routes/itemRequests.js
@@ -2,6 +2,7 @@ const express = require('express');
 const { Op } = require('sequelize');
 const { ItemRequest, ItemRequestResponse, User, Item } = require('../models');
 const { authenticateToken } = require('../middleware/auth');
+const logger = require('../utils/logger');
 const router = express.Router();
 
 router.get('/', async (req, res) => {
@@ -38,6 +39,15 @@ router.get('/', async (req, res) => {
       order: [['createdAt', 'DESC']]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item requests fetched", {
+      search,
+      status,
+      requestsCount: count,
+      page: parseInt(page),
+      limit: parseInt(limit)
+    });
+
     res.json({
       requests: rows,
       totalPages: Math.ceil(count / limit),
@@ -45,6 +55,12 @@ router.get('/', async (req, res) => {
       totalRequests: count
     });
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item requests fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      query: req.query
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -78,8 +94,20 @@ router.get('/my-requests', authenticateToken, async (req, res) => {
       order: [['createdAt', 'DESC']]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("User item requests fetched", {
+      userId: req.user.id,
+      requestsCount: requests.length
+    });
+
     res.json(requests);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("User item requests fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -115,8 +143,20 @@ router.get('/:id', async (req, res) => {
       return res.status(404).json({ error: 'Item request not found' });
     }
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item request fetched", {
+      requestId: req.params.id,
+      requesterId: request.requesterId
+    });
+
     res.json(request);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item request fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      requestId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -138,8 +178,22 @@ router.post('/', authenticateToken, async (req, res) => {
       ]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item request created", {
+      requestId: request.id,
+      requesterId: req.user.id,
+      title: req.body.title
+    });
+
     res.status(201).json(requestWithRequester);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item request creation failed", {
+      error: error.message,
+      stack: error.stack,
+      requesterId: req.user.id,
+      requestData: logger.sanitize(req.body)
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -168,8 +222,21 @@ router.put('/:id', authenticateToken, async (req, res) => {
       ]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item request updated", {
+      requestId: req.params.id,
+      requesterId: req.user.id
+    });
+
     res.json(updatedRequest);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item request update failed", {
+      error: error.message,
+      stack: error.stack,
+      requestId: req.params.id,
+      requesterId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -187,8 +254,22 @@ router.delete('/:id', authenticateToken, async (req, res) => {
     }
 
     await request.destroy();
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item request deleted", {
+      requestId: req.params.id,
+      requesterId: req.user.id
+    });
+
     res.status(204).send();
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item request deletion failed", {
+      error: error.message,
+      stack: error.stack,
+      requestId: req.params.id,
+      requesterId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -231,8 +312,22 @@ router.post('/:id/responses', authenticateToken, async (req, res) => {
       ]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item request response created", {
+      requestId: req.params.id,
+      responseId: response.id,
+      responderId: req.user.id
+    });
+
     res.status(201).json(responseWithDetails);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item request response creation failed", {
+      error: error.message,
+      stack: error.stack,
+      requestId: req.params.id,
+      responderId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -277,8 +372,23 @@ router.put('/responses/:responseId/status', authenticateToken, async (req, res)
       ]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item request response status updated", {
+      responseId: req.params.responseId,
+      newStatus: status,
+      requesterId: req.user.id,
+      requestFulfilled: status === 'accepted'
+    });
+
     res.json(updatedResponse);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item request response status update failed", {
+      error: error.message,
+      stack: error.stack,
+      responseId: req.params.responseId,
+      requesterId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
diff --git a/backend/routes/items.js b/backend/routes/items.js
index 813da8e..6fe8fd5 100644
--- a/backend/routes/items.js
+++ b/backend/routes/items.js
@@ -2,6 +2,7 @@ const express = require("express");
 const { Op } = require("sequelize");
 const { Item, User, Rental } = require("../models"); // Import from models/index.js to get models with associations
 const { authenticateToken } = require("../middleware/auth");
+const logger = require("../utils/logger");
 const router = express.Router();
 
 router.get("/", async (req, res) => {
@@ -60,6 +61,14 @@ router.get("/", async (req, res) => {
       return itemData;
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Items search completed", {
+      filters: { minPrice, maxPrice, city, zipCode, search },
+      resultsCount: count,
+      page: parseInt(page),
+      limit: parseInt(limit)
+    });
+
     res.json({
       items: itemsWithRoundedCoords,
       totalPages: Math.ceil(count / limit),
@@ -67,6 +76,12 @@ router.get("/", async (req, res) => {
       totalItems: count,
     });
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Items search failed", {
+      error: error.message,
+      stack: error.stack,
+      query: req.query
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -87,8 +102,20 @@ router.get("/recommendations", authenticateToken, async (req, res) => {
       order: [["createdAt", "DESC"]],
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Recommendations fetched", {
+      userId: req.user.id,
+      recommendationsCount: recommendations.length
+    });
+
     res.json(recommendations);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Recommendations fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -120,12 +147,25 @@ router.get('/:id/reviews', async (req, res) => {
       ? reviews.reduce((sum, review) => sum + review.itemRating, 0) / reviews.length 
       : 0;
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item reviews fetched", {
+      itemId: req.params.id,
+      reviewsCount: reviews.length,
+      averageRating
+    });
+
     res.json({
       reviews,
       averageRating,
       totalReviews: reviews.length
     });
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item reviews fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      itemId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -155,8 +195,20 @@ router.get("/:id", async (req, res) => {
       itemResponse.longitude = Math.round(parseFloat(itemResponse.longitude) * 100) / 100;
     }
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item fetched", {
+      itemId: req.params.id,
+      ownerId: item.ownerId
+    });
+
     res.json(itemResponse);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      itemId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -178,8 +230,22 @@ router.post("/", authenticateToken, async (req, res) => {
       ],
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item created", {
+      itemId: item.id,
+      ownerId: req.user.id,
+      itemName: req.body.name
+    });
+
     res.status(201).json(itemWithOwner);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item creation failed", {
+      error: error.message,
+      stack: error.stack,
+      ownerId: req.user.id,
+      itemData: logger.sanitize(req.body)
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -208,8 +274,21 @@ router.put("/:id", authenticateToken, async (req, res) => {
       ],
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item updated", {
+      itemId: req.params.id,
+      ownerId: req.user.id
+    });
+
     res.json(updatedItem);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item update failed", {
+      error: error.message,
+      stack: error.stack,
+      itemId: req.params.id,
+      ownerId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -227,8 +306,22 @@ router.delete("/:id", authenticateToken, async (req, res) => {
     }
 
     await item.destroy();
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Item deleted", {
+      itemId: req.params.id,
+      ownerId: req.user.id
+    });
+
     res.status(204).send();
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Item deletion failed", {
+      error: error.message,
+      stack: error.stack,
+      itemId: req.params.id,
+      ownerId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
diff --git a/backend/routes/maps.js b/backend/routes/maps.js
index b9592e5..65d526c 100644
--- a/backend/routes/maps.js
+++ b/backend/routes/maps.js
@@ -3,6 +3,7 @@ const router = express.Router();
 const { authenticateToken } = require("../middleware/auth");
 const rateLimiter = require("../middleware/rateLimiter");
 const googleMapsService = require("../services/googleMapsService");
+const logger = require("../utils/logger");
 
 // Input validation middleware
 const validateInput = (req, res, next) => {
@@ -34,8 +35,12 @@ const validateInput = (req, res, next) => {
 };
 
 // Error handling middleware
-const handleServiceError = (error, res) => {
-  console.error("Maps service error:", error.message);
+const handleServiceError = (error, res, req) => {
+  const reqLogger = logger.withRequestId(req?.id);
+  reqLogger.error("Maps service error", {
+    error: error.message,
+    stack: error.stack
+  });
 
   if (error.message.includes("API key not configured")) {
     return res.status(503).json({
@@ -87,17 +92,16 @@ router.post(
       );
 
       // Log request for monitoring (without sensitive data)
-      console.log(
-        `Places Autocomplete: user=${
-          req.user?.id || "anonymous"
-        }, query_length=${input.length}, results=${
-          result.predictions?.length || 0
-        }`
-      );
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Places Autocomplete request", {
+        userId: req.user?.id || "anonymous",
+        queryLength: input.length,
+        resultsCount: result.predictions?.length || 0
+      });
 
       res.json(result);
     } catch (error) {
-      handleServiceError(error, res);
+      handleServiceError(error, res, req);
     }
   }
 );
@@ -127,15 +131,15 @@ router.post(
       const result = await googleMapsService.getPlaceDetails(placeId, options);
 
       // Log request for monitoring
-      console.log(
-        `Place Details: user=${
-          req.user?.id || "anonymous"
-        }, placeId=${placeId.substring(0, 10)}...`
-      );
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Place Details request", {
+        userId: req.user?.id || "anonymous",
+        placeIdPrefix: placeId.substring(0, 10) + "..."
+      });
 
       res.json(result);
     } catch (error) {
-      handleServiceError(error, res);
+      handleServiceError(error, res, req);
     }
   }
 );
@@ -165,15 +169,15 @@ router.post(
       const result = await googleMapsService.geocodeAddress(address, options);
 
       // Log request for monitoring
-      console.log(
-        `Geocoding: user=${req.user?.id || "anonymous"}, address_length=${
-          address.length
-        }`
-      );
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Geocoding request", {
+        userId: req.user?.id || "anonymous",
+        addressLength: address.length
+      });
 
       res.json(result);
     } catch (error) {
-      handleServiceError(error, res);
+      handleServiceError(error, res, req);
     }
   }
 );
diff --git a/backend/routes/messages.js b/backend/routes/messages.js
index e15ac50..507b675 100644
--- a/backend/routes/messages.js
+++ b/backend/routes/messages.js
@@ -1,6 +1,7 @@
 const express = require('express');
 const { Message, User } = require('../models');
 const { authenticateToken } = require('../middleware/auth');
+const logger = require('../utils/logger');
 const router = express.Router();
 
 // Get all messages for the current user (inbox)
@@ -17,8 +18,21 @@ router.get('/', authenticateToken, async (req, res) => {
       ],
       order: [['createdAt', 'DESC']]
     });
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Messages inbox fetched", {
+      userId: req.user.id,
+      messageCount: messages.length
+    });
+
     res.json(messages);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Messages inbox fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -37,8 +51,21 @@ router.get('/sent', authenticateToken, async (req, res) => {
       ],
       order: [['createdAt', 'DESC']]
     });
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Sent messages fetched", {
+      userId: req.user.id,
+      messageCount: messages.length
+    });
+
     res.json(messages);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Sent messages fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -86,8 +113,22 @@ router.get('/:id', authenticateToken, async (req, res) => {
       await message.update({ isRead: true });
     }
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Message fetched", {
+      userId: req.user.id,
+      messageId: req.params.id,
+      markedAsRead: message.receiverId === req.user.id && !message.isRead
+    });
+
     res.json(message);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Message fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      messageId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -124,8 +165,23 @@ router.post('/', authenticateToken, async (req, res) => {
       }]
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Message sent", {
+      senderId: req.user.id,
+      receiverId: receiverId,
+      messageId: message.id,
+      isReply: !!parentMessageId
+    });
+
     res.status(201).json(messageWithSender);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Message send failed", {
+      error: error.message,
+      stack: error.stack,
+      senderId: req.user.id,
+      receiverId: req.body.receiverId
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -145,8 +201,22 @@ router.put('/:id/read', authenticateToken, async (req, res) => {
     }
 
     await message.update({ isRead: true });
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Message marked as read", {
+      userId: req.user.id,
+      messageId: req.params.id
+    });
+
     res.json(message);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Message mark as read failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      messageId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -160,8 +230,20 @@ router.get('/unread/count', authenticateToken, async (req, res) => {
         isRead: false
       }
     });
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Unread message count fetched", {
+      userId: req.user.id,
+      unreadCount: count
+    });
+
     res.json({ count });
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Unread message count fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
diff --git a/backend/routes/rentals.js b/backend/routes/rentals.js
index 7145438..5a5815e 100644
--- a/backend/routes/rentals.js
+++ b/backend/routes/rentals.js
@@ -4,6 +4,7 @@ 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 logger = require("../utils/logger");
 const router = express.Router();
 
 // Helper function to check and update review visibility
@@ -67,7 +68,12 @@ router.get("/my-rentals", authenticateToken, async (req, res) => {
 
     res.json(rentals);
   } catch (error) {
-    console.error("Error in my-rentals route:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error in my-rentals route", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: "Failed to fetch rentals" });
   }
 });
@@ -90,7 +96,12 @@ router.get("/my-listings", authenticateToken, async (req, res) => {
 
     res.json(rentals);
   } catch (error) {
-    console.error("Error in my-listings route:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error in my-listings route", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: "Failed to fetch listings" });
   }
 });
@@ -125,7 +136,13 @@ router.get("/:id", authenticateToken, async (req, res) => {
 
     res.json(rental);
   } catch (error) {
-    console.error("Error fetching rental:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error fetching rental", {
+      error: error.message,
+      stack: error.stack,
+      rentalId: req.params.id,
+      userId: req.user.id
+    });
     res.status(500).json({ error: "Failed to fetch rental" });
   }
 });
@@ -355,7 +372,13 @@ router.put("/:id/status", authenticateToken, async (req, res) => {
         res.json(updatedRental);
         return;
       } catch (paymentError) {
-        console.error("Payment failed during approval:", paymentError);
+        const reqLogger = logger.withRequestId(req.id);
+        reqLogger.error("Payment failed during approval", {
+          error: paymentError.message,
+          stack: paymentError.stack,
+          rentalId: req.params.id,
+          userId: req.user.id
+        });
         // Keep rental as pending, but inform of payment failure
         return res.status(400).json({
           error: "Payment failed during approval",
@@ -538,7 +561,15 @@ router.post("/calculate-fees", authenticateToken, async (req, res) => {
       display: displayFees,
     });
   } catch (error) {
-    console.error("Error calculating fees:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error calculating fees", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      startDate: req.query.startDate,
+      endDate: req.query.endDate,
+      itemId: req.query.itemId
+    });
     res.status(500).json({ error: "Failed to calculate fees" });
   }
 });
@@ -566,7 +597,12 @@ router.get("/earnings/status", authenticateToken, async (req, res) => {
 
     res.json(ownerRentals);
   } catch (error) {
-    console.error("Error getting earnings status:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error getting earnings status", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -580,7 +616,13 @@ router.get("/:id/refund-preview", authenticateToken, async (req, res) => {
     );
     res.json(preview);
   } catch (error) {
-    console.error("Error getting refund preview:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error getting refund preview", {
+      error: error.message,
+      stack: error.stack,
+      rentalId: req.params.id,
+      userId: req.user.id
+    });
     res.status(400).json({ error: error.message });
   }
 });
@@ -618,7 +660,13 @@ router.post("/:id/cancel", authenticateToken, async (req, res) => {
       refund: result.refund,
     });
   } catch (error) {
-    console.error("Error cancelling rental:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Error cancelling rental", {
+      error: error.message,
+      stack: error.stack,
+      rentalId: req.params.id,
+      userId: req.user.id
+    });
     res.status(400).json({ error: error.message });
   }
 });
diff --git a/backend/routes/stripe.js b/backend/routes/stripe.js
index 03f175f..320d9a8 100644
--- a/backend/routes/stripe.js
+++ b/backend/routes/stripe.js
@@ -2,6 +2,7 @@ const express = require("express");
 const { authenticateToken } = require("../middleware/auth");
 const { User, Item } = require("../models");
 const StripeService = require("../services/stripeService");
+const logger = require("../utils/logger");
 const router = express.Router();
 
 // Get checkout session status
@@ -11,6 +12,14 @@ router.get("/checkout-session/:sessionId", async (req, res) => {
 
     const session = await StripeService.getCheckoutSession(sessionId);
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Stripe checkout session retrieved", {
+      sessionId: sessionId,
+      status: session.status,
+      payment_status: session.payment_status,
+      metadata: session.metadata,
+    });
+
     res.json({
       status: session.status,
       payment_status: session.payment_status,
@@ -19,7 +28,12 @@ router.get("/checkout-session/:sessionId", async (req, res) => {
       metadata: session.metadata,
     });
   } catch (error) {
-    console.error("Error retrieving checkout session:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Stripe checkout session retrieval failed", {
+      error: error.message,
+      stack: error.stack,
+      sessionId: sessionId,
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -51,12 +65,23 @@ router.post("/accounts", authenticateToken, async (req, res) => {
       stripeConnectedAccountId: account.id,
     });
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Stripe connected account created", {
+      userId: req.user.id,
+      stripeConnectedAccountId: account.id,
+    });
+
     res.json({
       stripeConnectedAccountId: account.id,
       success: true,
     });
   } catch (error) {
-    console.error("Error creating connected account:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Stripe connected account creation failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -84,12 +109,25 @@ router.post("/account-links", authenticateToken, async (req, res) => {
       returnUrl
     );
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Stripe account link created", {
+      userId: req.user.id,
+      stripeConnectedAccountId: user.stripeConnectedAccountId,
+      expiresAt: accountLink.expires_at,
+    });
+
     res.json({
       url: accountLink.url,
       expiresAt: accountLink.expires_at,
     });
   } catch (error) {
-    console.error("Error creating account link:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Stripe account link creation failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      stripeConnectedAccountId: user?.stripeConnectedAccountId,
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -107,6 +145,14 @@ router.get("/account-status", authenticateToken, async (req, res) => {
       user.stripeConnectedAccountId
     );
 
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Stripe account status retrieved", {
+      userId: req.user.id,
+      stripeConnectedAccountId: user.stripeConnectedAccountId,
+      detailsSubmitted: accountStatus.details_submitted,
+      payoutsEnabled: accountStatus.payouts_enabled,
+    });
+
     res.json({
       accountId: accountStatus.id,
       detailsSubmitted: accountStatus.details_submitted,
@@ -115,59 +161,85 @@ router.get("/account-status", authenticateToken, async (req, res) => {
       requirements: accountStatus.requirements,
     });
   } catch (error) {
-    console.error("Error getting account status:", error);
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Stripe account status retrieval failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      stripeConnectedAccountId: user?.stripeConnectedAccountId,
+    });
     res.status(500).json({ error: error.message });
   }
 });
 
 // Create embedded setup checkout session for collecting payment method
-router.post("/create-setup-checkout-session", authenticateToken, async (req, res) => {
-  try {
-    const { rentalData } = req.body;
+router.post(
+  "/create-setup-checkout-session",
+  authenticateToken,
+  async (req, res) => {
+    try {
+      const { rentalData } = req.body;
 
-    const user = await User.findByPk(req.user.id);
-    
-    if (!user) {
-      return res.status(404).json({ error: "User not found" });
-    }
+      const user = await User.findByPk(req.user.id);
 
-    // Create or get Stripe customer
-    let stripeCustomerId = user.stripeCustomerId;
-    
-    if (!stripeCustomerId) {
-      // Create new Stripe customer
-      const customer = await StripeService.createCustomer({
-        email: user.email,
-        name: `${user.firstName} ${user.lastName}`,
-        metadata: {
-          userId: user.id.toString()
-        }
+      if (!user) {
+        return res.status(404).json({ error: "User not found" });
+      }
+
+      // Create or get Stripe customer
+      let stripeCustomerId = user.stripeCustomerId;
+
+      if (!stripeCustomerId) {
+        // Create new Stripe customer
+        const customer = await StripeService.createCustomer({
+          email: user.email,
+          name: `${user.firstName} ${user.lastName}`,
+          metadata: {
+            userId: user.id.toString(),
+          },
+        });
+
+        stripeCustomerId = customer.id;
+
+        // Save customer ID to user record
+        await user.update({ stripeCustomerId });
+      }
+
+      // Add rental data to metadata if provided
+      const metadata = rentalData
+        ? {
+            rentalData: JSON.stringify(rentalData),
+          }
+        : {};
+
+      const session = await StripeService.createSetupCheckoutSession({
+        customerId: stripeCustomerId,
+        metadata,
       });
-      
-      stripeCustomerId = customer.id;
-      
-      // Save customer ID to user record
-      await user.update({ stripeCustomerId });
+
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Stripe setup checkout session created", {
+        userId: req.user.id,
+        stripeCustomerId: stripeCustomerId,
+        sessionId: session.id,
+        hasRentalData: !!rentalData,
+      });
+
+      res.json({
+        clientSecret: session.client_secret,
+        sessionId: session.id,
+      });
+    } catch (error) {
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Stripe setup checkout session creation failed", {
+        error: error.message,
+        stack: error.stack,
+        userId: req.user.id,
+        stripeCustomerId: user?.stripeCustomerId,
+      });
+      res.status(500).json({ error: error.message });
     }
-    
-    // Add rental data to metadata if provided
-    const metadata = rentalData ? {
-      rentalData: JSON.stringify(rentalData)
-    } : {};
-    
-    const session = await StripeService.createSetupCheckoutSession({
-      customerId: stripeCustomerId,
-      metadata
-    });
-    
-    res.json({ 
-      clientSecret: session.client_secret,
-      sessionId: session.id
-    });
-  } catch (error) {
-    console.error("Error creating setup checkout session:", error);
-    res.status(500).json({ error: error.message });
   }
-});
+);
 
 module.exports = router;
diff --git a/backend/routes/users.js b/backend/routes/users.js
index d26083e..b6cf983 100644
--- a/backend/routes/users.js
+++ b/backend/routes/users.js
@@ -2,6 +2,7 @@ const express = require('express');
 const { User, UserAddress } = require('../models'); // Import from models/index.js to get models with associations
 const { authenticateToken } = require('../middleware/auth');
 const { uploadProfileImage } = require('../middleware/upload');
+const logger = require('../utils/logger');
 const fs = require('fs').promises;
 const path = require('path');
 const router = express.Router();
@@ -11,8 +12,20 @@ router.get('/profile', authenticateToken, async (req, res) => {
     const user = await User.findByPk(req.user.id, {
       attributes: { exclude: ['password'] }
     });
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("User profile fetched", {
+      userId: req.user.id
+    });
+
     res.json(user);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("User profile fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -24,8 +37,20 @@ router.get('/addresses', authenticateToken, async (req, res) => {
       where: { userId: req.user.id },
       order: [['isPrimary', 'DESC'], ['createdAt', 'ASC']]
     });
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("User addresses fetched", {
+      userId: req.user.id,
+      addressCount: addresses.length
+    });
+
     res.json(addresses);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("User addresses fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -36,8 +61,21 @@ router.post('/addresses', authenticateToken, async (req, res) => {
       ...req.body,
       userId: req.user.id
     });
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("User address created", {
+      userId: req.user.id,
+      addressId: address.id
+    });
+
     res.status(201).json(address);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("User address creation failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      addressData: logger.sanitize(req.body)
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -55,8 +93,22 @@ router.put('/addresses/:id', authenticateToken, async (req, res) => {
     }
     
     await address.update(req.body);
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("User address updated", {
+      userId: req.user.id,
+      addressId: req.params.id
+    });
+
     res.json(address);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("User address update failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      addressId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -74,8 +126,22 @@ router.delete('/addresses/:id', authenticateToken, async (req, res) => {
     }
     
     await address.destroy();
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("User address deleted", {
+      userId: req.user.id,
+      addressId: req.params.id
+    });
+
     res.status(204).send();
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("User address deletion failed", {
+      error: error.message,
+      stack: error.stack,
+      userId: req.user.id,
+      addressId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -121,13 +187,24 @@ router.get('/:id', async (req, res) => {
     const user = await User.findByPk(req.params.id, {
       attributes: { exclude: ['password', 'email', 'phone', 'address'] }
     });
-    
+
     if (!user) {
       return res.status(404).json({ error: 'User not found' });
     }
-    
+
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.info("Public user profile fetched", {
+      requestedUserId: req.params.id
+    });
+
     res.json(user);
   } catch (error) {
+    const reqLogger = logger.withRequestId(req.id);
+    reqLogger.error("Public user profile fetch failed", {
+      error: error.message,
+      stack: error.stack,
+      requestedUserId: req.params.id
+    });
     res.status(500).json({ error: error.message });
   }
 });
@@ -185,7 +262,11 @@ router.put('/profile', authenticateToken, async (req, res) => {
 router.post('/profile/image', authenticateToken, (req, res) => {
   uploadProfileImage(req, res, async (err) => {
     if (err) {
-      console.error('Upload error:', err);
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Profile image upload error", {
+        error: err.message,
+        userId: req.user.id
+      });
       return res.status(400).json({ error: err.message });
     }
 
@@ -201,7 +282,12 @@ router.post('/profile/image', authenticateToken, (req, res) => {
         try {
           await fs.unlink(oldImagePath);
         } catch (unlinkErr) {
-          console.error('Error deleting old image:', unlinkErr);
+          const reqLogger = logger.withRequestId(req.id);
+          reqLogger.warn("Error deleting old profile image", {
+            error: unlinkErr.message,
+            userId: req.user.id,
+            oldImagePath
+          });
         }
       }
 
@@ -210,13 +296,24 @@ router.post('/profile/image', authenticateToken, (req, res) => {
         profileImage: req.file.filename
       });
 
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.info("Profile image uploaded successfully", {
+        userId: req.user.id,
+        filename: req.file.filename
+      });
+
       res.json({
         message: 'Profile image uploaded successfully',
         filename: req.file.filename,
         imageUrl: `/uploads/profiles/${req.file.filename}`
       });
     } catch (error) {
-      console.error('Database update error:', error);
+      const reqLogger = logger.withRequestId(req.id);
+      reqLogger.error("Profile image database update failed", {
+        error: error.message,
+        stack: error.stack,
+        userId: req.user.id
+      });
       res.status(500).json({ error: 'Failed to update profile image' });
     }
   });
diff --git a/backend/server.js b/backend/server.js
index 81fde00..618465c 100644
--- a/backend/server.js
+++ b/backend/server.js
@@ -12,6 +12,8 @@ const path = require("path");
 const helmet = require("helmet");
 const { sequelize } = require("./models"); // Import from models/index.js to ensure associations are loaded
 const { cookieParser } = require("./middleware/csrf");
+const logger = require("./utils/logger");
+const morgan = require("morgan");
 
 const authRoutes = require("./routes/auth");
 const userRoutes = require("./routes/users");
@@ -34,6 +36,8 @@ const {
   sanitizeError,
 } = require("./middleware/security");
 const { generalLimiter } = require("./middleware/rateLimiter");
+const errorLogger = require("./middleware/errorLogger");
+const apiLogger = require("./middleware/apiLogger");
 
 // Apply security middleware
 app.use(enforceHTTPS);
@@ -60,6 +64,12 @@ app.use(
 // Cookie parser for CSRF
 app.use(cookieParser);
 
+// HTTP request logging
+app.use(morgan('combined', { stream: logger.stream }));
+
+// API request/response logging
+app.use("/api/", apiLogger);
+
 // General rate limiting for all routes
 app.use("/api/", generalLimiter);
 
@@ -107,6 +117,7 @@ app.get("/", (req, res) => {
 });
 
 // Error handling middleware (must be last)
+app.use(errorLogger);
 app.use(sanitizeError);
 
 const PORT = process.env.PORT || 5000;
@@ -114,15 +125,16 @@ const PORT = process.env.PORT || 5000;
 sequelize
   .sync({ alter: true })
   .then(() => {
-    console.log("Database synced");
+    logger.info("Database synced successfully");
 
     // Start the payout processor
     const payoutJobs = PayoutProcessor.startScheduledPayouts();
+    logger.info("Payout processor started");
 
     app.listen(PORT, () => {
-      console.log(`Server is running on port ${PORT}`);
+      logger.info(`Server is running on port ${PORT}`, { port: PORT, environment: env });
     });
   })
   .catch((err) => {
-    console.error("Unable to sync database:", err);
+    logger.error("Unable to sync database", { error: err.message, stack: err.stack });
   });
diff --git a/backend/utils/logger.js b/backend/utils/logger.js
new file mode 100644
index 0000000..0bc9f47
--- /dev/null
+++ b/backend/utils/logger.js
@@ -0,0 +1,137 @@
+const winston = require('winston');
+const DailyRotateFile = require('winston-daily-rotate-file');
+
+// Define log levels and colors
+const logLevels = {
+  error: 0,
+  warn: 1,
+  info: 2,
+  http: 3,
+  debug: 4,
+};
+
+winston.addColors({
+  error: 'red',
+  warn: 'yellow',
+  info: 'green',
+  http: 'magenta',
+  debug: 'white',
+});
+
+// Determine log level based on environment
+const level = () => {
+  const env = process.env.NODE_ENV || 'dev';
+  const isDevelopment = env === 'dev' || env === 'development';
+  return isDevelopment ? 'debug' : process.env.LOG_LEVEL || 'info';
+};
+
+// Define log format
+const logFormat = winston.format.combine(
+  winston.format.timestamp({ format: 'YYYY-MM-DD HH:mm:ss:ms' }),
+  winston.format.colorize({ all: true }),
+  winston.format.printf((info) => {
+    if (info.stack) {
+      return `${info.timestamp} ${info.level}: ${info.message}\n${info.stack}`;
+    }
+    return `${info.timestamp} ${info.level}: ${info.message}`;
+  }),
+);
+
+// Define JSON format for file logging
+const jsonFormat = winston.format.combine(
+  winston.format.timestamp({ format: 'YYYY-MM-DD HH:mm:ss:ms' }),
+  winston.format.errors({ stack: true }),
+  winston.format.json()
+);
+
+// Create transports array
+const transports = [
+  // Console transport for development
+  new winston.transports.Console({
+    level: level(),
+    format: logFormat,
+  }),
+
+  // Daily rotate file for all logs
+  new DailyRotateFile({
+    filename: 'logs/application-%DATE%.log',
+    datePattern: 'YYYY-MM-DD',
+    maxSize: '20m',
+    maxFiles: '14d',
+    level: 'info',
+    format: jsonFormat,
+  }),
+
+  // Daily rotate file for error logs only
+  new DailyRotateFile({
+    filename: 'logs/error-%DATE%.log',
+    datePattern: 'YYYY-MM-DD',
+    maxSize: '20m',
+    maxFiles: '14d',
+    level: 'error',
+    format: jsonFormat,
+  }),
+];
+
+// Create the logger
+const logger = winston.createLogger({
+  level: level(),
+  levels: logLevels,
+  format: jsonFormat,
+  transports,
+  exceptionHandlers: [
+    new winston.transports.File({ filename: 'logs/exceptions.log' })
+  ],
+  rejectionHandlers: [
+    new winston.transports.File({ filename: 'logs/rejections.log' })
+  ],
+});
+
+// Create a stream object for Morgan
+logger.stream = {
+  write: (message) => {
+    // Remove trailing newline from Morgan and log as http level
+    logger.http(message.trim());
+  },
+};
+
+// Add request ID correlation function
+logger.withRequestId = (requestId) => {
+  return {
+    error: (message, meta = {}) => logger.error(message, { ...meta, requestId }),
+    warn: (message, meta = {}) => logger.warn(message, { ...meta, requestId }),
+    info: (message, meta = {}) => logger.info(message, { ...meta, requestId }),
+    http: (message, meta = {}) => logger.http(message, { ...meta, requestId }),
+    debug: (message, meta = {}) => logger.debug(message, { ...meta, requestId }),
+  };
+};
+
+// Add sanitization helper for sensitive data
+logger.sanitize = (data) => {
+  if (typeof data !== 'object' || data === null) {
+    return data;
+  }
+
+  const sensitiveFields = [
+    'password', 'token', 'secret', 'key', 'authorization', 'cookie',
+    'ssn', 'credit_card', 'cvv', 'pin', 'account_number'
+  ];
+
+  const sanitized = JSON.parse(JSON.stringify(data));
+
+  const sanitizeObject = (obj) => {
+    for (const [key, value] of Object.entries(obj)) {
+      const lowerKey = key.toLowerCase();
+      if (sensitiveFields.some(field => lowerKey.includes(field))) {
+        obj[key] = '[REDACTED]';
+      } else if (typeof value === 'object' && value !== null) {
+        sanitizeObject(value);
+      }
+    }
+  };
+
+  sanitizeObject(sanitized);
+  return sanitized;
+};
+
+module.exports = logger;
\ No newline at end of file