diff --git a/api/config/__tests__/parsers.spec.js b/api/config/__tests__/parsers.spec.js
index f54675ce3a..4c78360953 100644
--- a/api/config/__tests__/parsers.spec.js
+++ b/api/config/__tests__/parsers.spec.js
@@ -30,6 +30,18 @@ describe('formatConsoleMeta', () => {
     expect(meta).toContain('"messagesToRefineCount":42');
   });
 
+  it('omits the system tenant sentinel from metadata trailers', () => {
+    const meta = formatConsoleMeta({
+      level: 'warn',
+      message: 'system task',
+      timestamp: 'ts',
+      tenantId: '__SYSTEM__',
+      userId: 'user-1',
+    });
+
+    expect(meta).toBe('{"userId":"user-1"}');
+  });
+
   it('ignores reserved winston keys but preserves legitimate fields like _id', () => {
     const meta = formatConsoleMeta({
       level: 'error',
@@ -315,6 +327,66 @@ describe('debugTraverse', () => {
     expect(tenantMatches.length).toBe(1);
   });
 
+  it('appends request context metadata for non-debug lines', () => {
+    const out = runFormatter(
+      buildInfo('info', {
+        tenantId: 'tenant-1',
+        userId: 'user-1',
+        requestId: 'req-1',
+      }),
+    );
+
+    expect(out).toContain('"tenantId":"tenant-1"');
+    expect(out).toContain('"userId":"user-1"');
+    expect(out).toContain('"requestId":"req-1"');
+  });
+
+  it('does not append the system tenant sentinel as tenantId', () => {
+    const out = runFormatter(
+      buildInfo('info', {
+        tenantId: '__SYSTEM__',
+        userId: 'user-1',
+        requestId: 'req-1',
+      }),
+    );
+
+    expect(out).not.toContain('__SYSTEM__');
+    expect(out).not.toContain('"tenantId"');
+    expect(out).toContain('"userId":"user-1"');
+    expect(out).toContain('"requestId":"req-1"');
+  });
+
+  it('omits the system tenant sentinel from debug object metadata', () => {
+    const out = runFormatter(
+      buildInfo('debug', {
+        tenantId: '__SYSTEM__',
+        userId: 'user-1',
+      }),
+    );
+
+    expect(out).not.toContain('__SYSTEM__');
+    expect(out).not.toMatch(/tenantId:/);
+    expect(out).toContain('userId');
+  });
+
+  it('appends request context metadata for debug lines without object metadata', () => {
+    const info = {
+      level: 'debug',
+      message: 'prefix:',
+      timestamp: 'ts',
+      tenantId: 'tenant-1',
+      userId: 'user-1',
+      requestId: 'req-1',
+      [SPLAT_SYMBOL]: ['detailValueXYZ'],
+    };
+    const out = runFormatter(info);
+
+    expect(out).toContain('detailValueXYZ');
+    expect(out).toContain('"tenantId":"tenant-1"');
+    expect(out).toContain('"userId":"user-1"');
+    expect(out).toContain('"requestId":"req-1"');
+  });
+
   it('omits numeric splat-artifact keys from the traversed output', () => {
     const info = {
       level: 'error',
diff --git a/api/config/parsers.js b/api/config/parsers.js
index 111f3f6a7d..477e371253 100644
--- a/api/config/parsers.js
+++ b/api/config/parsers.js
@@ -18,6 +18,8 @@ const sensitiveKeys = [
 ];
 
 const NUMERIC_KEY_RE = /^\d+$/;
+const LOG_CONTEXT_KEYS = ['tenantId', 'userId', 'requestId'];
+const SYSTEM_TENANT_ID = '__SYSTEM__';
 
 /**
  * Redacts sensitive information from a console message and trims it to a specified length if provided.
@@ -122,6 +124,9 @@ function extractMetaObject(source) {
       continue;
     }
     const value = source[key];
+    if (key === 'tenantId' && value === SYSTEM_TENANT_ID) {
+      continue;
+    }
     if (value === undefined || value === null || value === '') {
       continue;
     }
@@ -197,6 +202,23 @@ function formatConsoleMeta(info) {
   }
 }
 
+function formatRequestContext(info) {
+  if (info == null || typeof info !== 'object') {
+    return '';
+  }
+  const context = {};
+  for (const key of LOG_CONTEXT_KEYS) {
+    const value = info[key];
+    if (key === 'tenantId' && value === SYSTEM_TENANT_ID) {
+      continue;
+    }
+    if (typeof value === 'string' && value) {
+      context[key] = value;
+    }
+  }
+  return Object.keys(context).length > 0 ? JSON.stringify(context) : '';
+}
+
 /**
  * Formats log messages for file and debug-console transports. Three paths:
  * - `warn` / `error`: append a compact single-line JSON metadata trailer
@@ -207,7 +229,7 @@ function formatConsoleMeta(info) {
  *   Redaction on this path is not applied here (debug-file consumers
  *   historically accept raw detail).
  * - Other levels: return the truncated `"<timestamp> <level>: <message>"`
- *   line with no metadata.
+ *   line with request context metadata when present.
  *
  * @param {Object} options - The options for formatting log messages.
  * @param {string} options.level - The log level.
@@ -245,31 +267,41 @@ const debugTraverse = winston.format.printf(({ level, message, timestamp, ...met
 
   try {
     if (level !== 'debug') {
-      return msg;
+      const trailer = formatRequestContext(metadata);
+      return trailer ? `${msg} ${trailer}` : msg;
     }
 
     if (!metadata) {
       return msg;
     }
 
+    const appendMetadataTrailer = (line) => {
+      const trailer = formatRequestContext(metadata);
+      return trailer ? `${line} ${trailer}` : line;
+    };
+
     const debugValue = metadata[SPLAT_SYMBOL]?.[0];
 
     if (!debugValue) {
-      return msg;
+      return appendMetadataTrailer(msg);
     }
 
     if (debugValue && Array.isArray(debugValue)) {
       msg += `\n${JSON.stringify(debugValue.map(condenseArray))}`;
-      return msg;
+      return appendMetadataTrailer(msg);
     }
 
     if (typeof debugValue !== 'object') {
-      return (msg += ` ${debugValue}`);
+      msg += ` ${debugValue}`;
+      return appendMetadataTrailer(msg);
     }
 
     msg += '\n{';
 
     const copy = klona(metadata);
+    if (copy.tenantId === SYSTEM_TENANT_ID) {
+      delete copy.tenantId;
+    }
     traverse(copy).forEach(function (value) {
       if (typeof this?.key === 'symbol') {
         return;
diff --git a/api/config/winston.js b/api/config/winston.js
index c077cf5bf8..163e0b4eab 100644
--- a/api/config/winston.js
+++ b/api/config/winston.js
@@ -2,6 +2,12 @@ const path = require('path');
 const fs = require('fs');
 const winston = require('winston');
 require('winston-daily-rotate-file');
+const {
+  getTenantId,
+  getUserId,
+  getRequestId,
+  SYSTEM_TENANT_ID,
+} = require('@librechat/data-schemas');
 const {
   redactFormat,
   redactMessage,
@@ -63,6 +69,44 @@ const levels = {
   silly: 7,
 };
 
+const LOG_CONTEXT_KEYS = ['tenantId', 'userId', 'requestId'];
+
+const getLogTenantId = () => {
+  const tenantId = getTenantId();
+  return tenantId === SYSTEM_TENANT_ID ? undefined : tenantId;
+};
+
+const requestContextFormat = winston.format((info) => {
+  if (info.tenantId === SYSTEM_TENANT_ID) {
+    delete info.tenantId;
+  }
+  const context = {
+    tenantId: getLogTenantId(),
+    userId: getUserId(),
+    requestId: getRequestId(),
+  };
+  LOG_CONTEXT_KEYS.forEach((key) => {
+    if (context[key] && info[key] == null) {
+      info[key] = context[key];
+    }
+  });
+  return info;
+});
+
+const formatRequestContext = (info) => {
+  const context = {};
+  LOG_CONTEXT_KEYS.forEach((key) => {
+    const value = info[key];
+    if (key === 'tenantId' && value === SYSTEM_TENANT_ID) {
+      return;
+    }
+    if (typeof value === 'string' && value) {
+      context[key] = value;
+    }
+  });
+  return Object.keys(context).length > 0 ? JSON.stringify(context) : '';
+};
+
 winston.addColors({
   info: 'green', // fontStyle color
   warn: 'italic yellow',
@@ -81,6 +125,7 @@ const fileFormat = winston.format.combine(
   winston.format.timestamp({ format: () => new Date().toISOString() }),
   winston.format.errors({ stack: true }),
   winston.format.splat(),
+  requestContextFormat(),
   // redactErrors(),
 );
 
@@ -112,20 +157,16 @@ if (useDebugLogging) {
 
 const consoleFormat = winston.format.combine(
   redactFormat(),
+  requestContextFormat(),
   winston.format.colorize({ all: true }),
   winston.format.timestamp({ format: 'YYYY-MM-DD HH:mm:ss' }),
   // redactErrors(),
   winston.format.printf((info) => {
     const base = `${info.timestamp} ${info.level}: ${info.message}`;
     const isErrorOrWarn = info.level.includes('error') || info.level.includes('warn');
-
-    if (isErrorOrWarn) {
-      const metaTrailer = formatConsoleMeta(info);
-      const line = metaTrailer ? `${base} ${metaTrailer}` : base;
-      return redactMessage(line);
-    }
-
-    return base;
+    const metaTrailer = isErrorOrWarn ? formatConsoleMeta(info) : formatRequestContext(info);
+    const line = metaTrailer ? `${base} ${metaTrailer}` : base;
+    return isErrorOrWarn ? redactMessage(line) : line;
   }),
 );
 
diff --git a/api/server/middleware/__tests__/requireJwtAuth.spec.js b/api/server/middleware/__tests__/requireJwtAuth.spec.js
index 7f0963398d..4059be2409 100644
--- a/api/server/middleware/__tests__/requireJwtAuth.spec.js
+++ b/api/server/middleware/__tests__/requireJwtAuth.spec.js
@@ -41,25 +41,42 @@ jest.mock('@librechat/data-schemas', () => {
   const tenantStorage = new AsyncLocalStorage();
   return {
     getTenantId: () => tenantStorage.getStore()?.tenantId,
+    getUserId: () => tenantStorage.getStore()?.userId,
+    getRequestId: () => tenantStorage.getStore()?.requestId,
     tenantStorage,
   };
 });
 
 // Mock @librechat/api — the real tenantContextMiddleware is TS and cannot be
 // required directly from CJS tests. This thin wrapper mirrors the real logic
-// (read req.user.tenantId, call tenantStorage.run) using the same data-schemas
+// (read request context, call tenantStorage.run) using the same data-schemas
 // primitives. The real implementation is covered by packages/api tenant.spec.ts.
 jest.mock('@librechat/api', () => {
   const { tenantStorage } = require('@librechat/data-schemas');
+  const normalizeContextValue = (value) => {
+    const trimmed = value?.trim?.();
+    return trimmed || undefined;
+  };
+  const getUserId = (user) =>
+    normalizeContextValue(user?.id?.toString?.()) ?? normalizeContextValue(user?._id?.toString?.());
+  const getRequestId = (req) =>
+    normalizeContextValue(req.requestId) ??
+    normalizeContextValue(req.id) ??
+    normalizeContextValue(req.headers?.['x-request-id']) ??
+    normalizeContextValue(req.headers?.['x-correlation-id']);
   return {
     isEnabled: jest.fn(() => false),
     maybeRefreshCloudFrontAuthCookiesMiddleware: jest.fn((req, res, next) => next()),
     tenantContextMiddleware: (req, res, next) => {
-      const tenantId = req.user?.tenantId;
-      if (!tenantId) {
+      const context = {
+        tenantId: normalizeContextValue(req.user?.tenantId),
+        userId: getUserId(req.user),
+        requestId: getRequestId(req),
+      };
+      if (!context.tenantId && !context.userId && !context.requestId) {
         return next();
       }
-      return tenantStorage.run({ tenantId }, async () => next());
+      return tenantStorage.run(context, async () => next());
     },
   };
 });
@@ -67,7 +84,7 @@ jest.mock('@librechat/api', () => {
 // ── Helpers ─────────────────────────────────────────────────────────────
 
 const requireJwtAuth = require('../requireJwtAuth');
-const { getTenantId } = require('@librechat/data-schemas');
+const { getTenantId, getUserId } = require('@librechat/data-schemas');
 const { isEnabled, maybeRefreshCloudFrontAuthCookiesMiddleware } = require('@librechat/api');
 const passport = require('passport');
 
@@ -151,6 +168,27 @@ describe('requireJwtAuth tenant context chaining', () => {
     expect(next).toHaveBeenCalled();
   });
 
+  it('refreshes CloudFront auth cookies inside the request context', () => {
+    let observedContext;
+    maybeRefreshCloudFrontAuthCookiesMiddleware.mockImplementationOnce(
+      (_req, _res, middlewareNext) => {
+        observedContext = {
+          tenantId: getTenantId(),
+          userId: getUserId(),
+        };
+        middlewareNext();
+      },
+    );
+    const req = mockReq({ id: 'user-123', tenantId: 'tenant-abc', role: 'user' });
+    const res = mockRes();
+    const next = jest.fn();
+
+    requireJwtAuth(req, res, next);
+
+    expect(observedContext).toEqual({ tenantId: 'tenant-abc', userId: 'user-123' });
+    expect(next).toHaveBeenCalled();
+  });
+
   it('ALS tenant context is NOT set when user has no tenantId', async () => {
     const tenantId = await runAuth({ role: 'user' });
     expect(tenantId).toBeUndefined();
diff --git a/api/server/middleware/requireJwtAuth.js b/api/server/middleware/requireJwtAuth.js
index e9abbc7fa8..935957e913 100644
--- a/api/server/middleware/requireJwtAuth.js
+++ b/api/server/middleware/requireJwtAuth.js
@@ -35,8 +35,8 @@ const refreshCloudFrontCookies =
  * Switches between JWT and OpenID authentication based on cookies and environment settings.
  *
  * After successful authentication (req.user populated), automatically chains into
- * `tenantContextMiddleware` to propagate `req.user.tenantId` into AsyncLocalStorage
- * for downstream Mongoose tenant isolation.
+ * `tenantContextMiddleware` to propagate request context into AsyncLocalStorage
+ * for downstream Mongoose tenant isolation and structured logging.
  */
 const requireJwtAuth = (req, res, next) => {
   const cookieHeader = req.headers.cookie;
@@ -71,12 +71,11 @@ const requireJwtAuth = (req, res, next) => {
       }
       req.user = user;
       req.authStrategy = strategy;
-      refreshCloudFrontCookies(req, res, (refreshErr) => {
-        if (refreshErr) {
-          return next(refreshErr);
+      tenantContextMiddleware(req, res, (tenantErr) => {
+        if (tenantErr) {
+          return next(tenantErr);
         }
-        // req.user is now populated by passport — set up tenant ALS context
-        tenantContextMiddleware(req, res, next);
+        refreshCloudFrontCookies(req, res, next);
       });
     })(req, res, next);
   };
diff --git a/api/server/services/AuthService.js b/api/server/services/AuthService.js
index 943c5a81f6..24374ef4c6 100644
--- a/api/server/services/AuthService.js
+++ b/api/server/services/AuthService.js
@@ -448,6 +448,8 @@ const getCloudFrontAuthCookieSkipReason = (scope) => {
   return null;
 };
 
+const shouldLogCloudFrontAuthCookieSkip = (reason) => reason !== 'cloudfront_disabled';
+
 /**
  * Refreshes CloudFront signed cookies for authenticated image/avatar access.
  * @param {ServerRequest | null} req
@@ -477,15 +479,17 @@ const setCloudFrontAuthCookies = (req, res, user, options = {}) => {
   };
   const skipReason = getCloudFrontAuthCookieSkipReason(scope);
   if (skipReason) {
-    logger.debug('[setCloudFrontAuthCookies] CloudFront auth cookies skipped', {
-      attempted: false,
-      set: false,
-      reason: skipReason,
-      has_user_id: Boolean(scope.userId),
-      has_tenant_scope: Boolean(scope.tenantId),
-      has_storage_region: Boolean(scope.storageRegion),
-      has_previous_scope: Boolean(getPreviousCloudFrontScope(req)?.userId),
-    });
+    if (shouldLogCloudFrontAuthCookieSkip(skipReason)) {
+      logger.debug('[setCloudFrontAuthCookies] CloudFront auth cookies skipped', {
+        attempted: false,
+        set: false,
+        reason: skipReason,
+        has_user_id: Boolean(scope.userId),
+        has_tenant_scope: Boolean(scope.tenantId),
+        has_storage_region: Boolean(scope.storageRegion),
+        has_previous_scope: Boolean(getPreviousCloudFrontScope(req)?.userId),
+      });
+    }
     return false;
   }
 
diff --git a/api/server/services/AuthService.spec.js b/api/server/services/AuthService.spec.js
index c81b78e8e1..95a208c5c8 100644
--- a/api/server/services/AuthService.spec.js
+++ b/api/server/services/AuthService.spec.js
@@ -576,13 +576,9 @@ describe('CloudFront cookie integration', () => {
 
       expect(result).toBe(false);
       expect(setCloudFrontCookies).not.toHaveBeenCalled();
-      expect(logger.debug).toHaveBeenCalledWith(
+      expect(logger.debug).not.toHaveBeenCalledWith(
         '[setCloudFrontAuthCookies] CloudFront auth cookies skipped',
-        expect.objectContaining({
-          attempted: false,
-          set: false,
-          reason: 'cloudfront_disabled',
-        }),
+        expect.any(Object),
       );
     });
 
diff --git a/packages/api/src/cdn/__tests__/cloudfront-cookies.test.ts b/packages/api/src/cdn/__tests__/cloudfront-cookies.test.ts
index b9d22048e3..940dece049 100644
--- a/packages/api/src/cdn/__tests__/cloudfront-cookies.test.ts
+++ b/packages/api/src/cdn/__tests__/cloudfront-cookies.test.ts
@@ -840,6 +840,10 @@ describe('maybeRefreshCloudFrontAuthCookies', () => {
 
     expect(result).toMatchObject({ enabled: false, attempted: false, refreshed: false });
     expect(mockGetSignedCookies).not.toHaveBeenCalled();
+    expect(mockLogger.debug).not.toHaveBeenCalledWith(
+      '[maybeRefreshCloudFrontAuthCookies] CloudFront auth cookies skipped',
+      expect.any(Object),
+    );
   });
 
   it('does not refresh when imageSigning is not cookies', () => {
@@ -851,6 +855,10 @@ describe('maybeRefreshCloudFrontAuthCookies', () => {
 
     expect(result).toMatchObject({ enabled: false, attempted: false, refreshed: false });
     expect(mockGetSignedCookies).not.toHaveBeenCalled();
+    expect(mockLogger.debug).not.toHaveBeenCalledWith(
+      '[maybeRefreshCloudFrontAuthCookies] CloudFront auth cookies skipped',
+      expect.any(Object),
+    );
   });
 
   it('force-refreshes even when the scope cookie is fresh without calling OIDC refresh', () => {
diff --git a/packages/api/src/cdn/cloudfront-cookies.ts b/packages/api/src/cdn/cloudfront-cookies.ts
index 98de321043..8f1add221b 100644
--- a/packages/api/src/cdn/cloudfront-cookies.ts
+++ b/packages/api/src/cdn/cloudfront-cookies.ts
@@ -312,6 +312,10 @@ function getCloudFrontCookieSkipReason(scope: CloudFrontCookieScope): string | n
   return null;
 }
 
+function shouldLogCloudFrontCookieSkip(reason: string): boolean {
+  return reason !== 'cloudfront_disabled';
+}
+
 function getScopeRefreshReason(
   previousScope: CloudFrontCookieScope | null,
   currentScope: CloudFrontCookieScope,
@@ -540,14 +544,16 @@ export function maybeRefreshCloudFrontAuthCookies(
     const timing = getCloudFrontCookieTiming();
 
     if (skipReason) {
-      logger.debug('[maybeRefreshCloudFrontAuthCookies] CloudFront auth cookies skipped', {
-        attempted: false,
-        refreshed: false,
-        reason: skipReason,
-        has_user_id: Boolean(scope.userId),
-        has_tenant_scope: Boolean(scope.tenantId),
-        has_storage_region: Boolean(scope.storageRegion),
-      });
+      if (shouldLogCloudFrontCookieSkip(skipReason)) {
+        logger.debug('[maybeRefreshCloudFrontAuthCookies] CloudFront auth cookies skipped', {
+          attempted: false,
+          refreshed: false,
+          reason: skipReason,
+          has_user_id: Boolean(scope.userId),
+          has_tenant_scope: Boolean(scope.tenantId),
+          has_storage_region: Boolean(scope.storageRegion),
+        });
+      }
       return {
         enabled: false,
         attempted: false,
diff --git a/packages/api/src/middleware/__tests__/tenant.spec.ts b/packages/api/src/middleware/__tests__/tenant.spec.ts
index d393cdfe0d..6a78ad3098 100644
--- a/packages/api/src/middleware/__tests__/tenant.spec.ts
+++ b/packages/api/src/middleware/__tests__/tenant.spec.ts
@@ -1,5 +1,11 @@
 import { unlink } from 'fs/promises';
-import { getTenantId, SYSTEM_TENANT_ID } from '@librechat/data-schemas';
+import {
+  getTenantId,
+  getUserId,
+  getRequestId,
+  SYSTEM_TENANT_ID,
+  logger,
+} from '@librechat/data-schemas';
 import type { Response, NextFunction } from 'express';
 import type { ServerRequest } from '~/types/http';
 // Import directly from source file — _resetTenantMiddlewareStrictCache is intentionally
@@ -18,11 +24,18 @@ jest.mock('fs/promises', () => ({
 const unlinkMock = unlink as jest.MockedFunction<typeof unlink>;
 
 function mockReq(user?: Record<string, unknown>): ServerRequest {
-  return { user } as unknown as ServerRequest;
+  return { headers: {}, user } as unknown as ServerRequest;
 }
 
 function mockTenantReq(user?: Record<string, unknown>, tenantId?: string): ServerRequest {
-  return { user, tenantId } as unknown as ServerRequest;
+  return { headers: {}, user, tenantId } as unknown as ServerRequest;
+}
+
+function mockReqWithHeaders(
+  user: Record<string, unknown> | undefined,
+  headers: Record<string, string>,
+): ServerRequest {
+  return { headers, user } as unknown as ServerRequest;
 }
 
 function mockRes(): Response {
@@ -43,11 +56,32 @@ function runMiddleware(req: ServerRequest, res: Response): Promise<string | unde
   });
 }
 
+function runMiddlewareContext(
+  req: ServerRequest,
+  res: Response,
+): Promise<{
+  tenantId?: string;
+  userId?: string;
+  requestId?: string;
+}> {
+  return new Promise((resolve) => {
+    const next: NextFunction = () => {
+      resolve({
+        tenantId: getTenantId(),
+        userId: getUserId(),
+        requestId: getRequestId(),
+      });
+    };
+    tenantContextMiddleware(req, res, next);
+  });
+}
+
 describe('tenantContextMiddleware', () => {
   afterEach(() => {
     _resetTenantMiddlewareStrictCache();
     delete process.env.TENANT_ISOLATION_STRICT;
     unlinkMock.mockClear();
+    jest.restoreAllMocks();
   });
 
   it('sets ALS tenant context for authenticated requests with tenantId', async () => {
@@ -58,6 +92,22 @@ describe('tenantContextMiddleware', () => {
     expect(tenantId).toBe('tenant-x');
   });
 
+  it('sets ALS user and request context for authenticated tenant requests', async () => {
+    const req = mockReqWithHeaders(
+      { id: 'user-123', tenantId: 'tenant-x', role: 'user' },
+      { 'x-request-id': 'req-abc' },
+    );
+    const res = mockRes();
+
+    const context = await runMiddlewareContext(req, res);
+
+    expect(context).toEqual({
+      tenantId: 'tenant-x',
+      userId: 'user-123',
+      requestId: 'req-abc',
+    });
+  });
+
   it('is a no-op for unauthenticated requests (no user)', async () => {
     const req = mockReq();
     const res = mockRes();
@@ -74,6 +124,22 @@ describe('tenantContextMiddleware', () => {
     expect(tenantId).toBeUndefined();
   });
 
+  it('keeps user context in non-strict single-tenant mode', async () => {
+    const req = mockReqWithHeaders(
+      { id: 'single-user', role: 'user' },
+      { 'x-request-id': 'req-1' },
+    );
+    const res = mockRes();
+
+    const context = await runMiddlewareContext(req, res);
+
+    expect(context).toEqual({
+      tenantId: undefined,
+      userId: 'single-user',
+      requestId: 'req-1',
+    });
+  });
+
   it('returns 403 when user has no tenantId in strict mode', async () => {
     process.env.TENANT_ISOLATION_STRICT = 'true';
     _resetTenantMiddlewareStrictCache();
@@ -122,6 +188,7 @@ describe('restoreTenantContextFromReq', () => {
     _resetTenantMiddlewareStrictCache();
     delete process.env.TENANT_ISOLATION_STRICT;
     unlinkMock.mockClear();
+    jest.restoreAllMocks();
   });
 
   it('restores ALS tenant context from req.user.tenantId', async () => {
@@ -139,6 +206,34 @@ describe('restoreTenantContextFromReq', () => {
     expect(tenantId).toBe('tenant-user');
   });
 
+  it('restores user and request context alongside tenant context', async () => {
+    const req = mockReqWithHeaders(
+      { id: 'restore-user', tenantId: 'tenant-user', role: 'user' },
+      { 'x-correlation-id': 'corr-123' },
+    );
+    const res = mockRes();
+
+    const context = await new Promise<{
+      tenantId?: string;
+      userId?: string;
+      requestId?: string;
+    }>((resolve) => {
+      restoreTenantContextFromReq(req, res, () => {
+        resolve({
+          tenantId: getTenantId(),
+          userId: getUserId(),
+          requestId: getRequestId(),
+        });
+      });
+    });
+
+    expect(context).toEqual({
+      tenantId: 'tenant-user',
+      userId: 'restore-user',
+      requestId: 'corr-123',
+    });
+  });
+
   it('prefers server-resolved req.tenantId over req.user.tenantId', async () => {
     const req = mockTenantReq({ tenantId: 'tenant-user', role: 'user' }, 'tenant-request');
     const res = mockRes();
@@ -187,6 +282,37 @@ describe('restoreTenantContextFromReq', () => {
     expect(next).not.toHaveBeenCalled();
   });
 
+  it('keeps request context while cleaning up rejected strict-mode uploads', async () => {
+    process.env.TENANT_ISOLATION_STRICT = 'true';
+    _resetTenantMiddlewareStrictCache();
+    unlinkMock.mockRejectedValueOnce(new Error('unlink failed'));
+    let observedContext: { userId?: string; requestId?: string } | undefined;
+    jest.spyOn(logger, 'error').mockImplementation(() => {
+      observedContext = {
+        userId: getUserId(),
+        requestId: getRequestId(),
+      };
+      return logger;
+    });
+
+    const req = {
+      ...mockReqWithHeaders({ id: 'strict-user', role: 'user' }, { 'x-request-id': 'req-strict' }),
+      file: { path: '/tmp/no-tenant-upload' },
+    } as ServerRequest;
+    const res = mockRes();
+    const next: NextFunction = jest.fn();
+
+    await restoreTenantContextFromReq(req, res, next);
+
+    expect(logger.error).toHaveBeenCalledWith(
+      '[restoreTenantContextFromReq] Failed to delete rejected upload:',
+      expect.objectContaining({ path: '/tmp/no-tenant-upload' }),
+    );
+    expect(observedContext).toEqual({ userId: 'strict-user', requestId: 'req-strict' });
+    expect(res.status).toHaveBeenCalledWith(403);
+    expect(next).not.toHaveBeenCalled();
+  });
+
   it('rejects the system tenant sentinel for request-owned work', async () => {
     const req = mockReq({ tenantId: SYSTEM_TENANT_ID, role: 'user' });
     const res = mockRes();
@@ -198,6 +324,37 @@ describe('restoreTenantContextFromReq', () => {
     expect(next).not.toHaveBeenCalled();
   });
 
+  it('rejects a normalized system tenant sentinel for request-owned work', async () => {
+    const req = mockTenantReq({ role: 'user' }, ` ${SYSTEM_TENANT_ID} `);
+    const res = mockRes();
+    const next: NextFunction = jest.fn();
+
+    await restoreTenantContextFromReq(req, res, next);
+
+    expect(res.status).toHaveBeenCalledWith(403);
+    expect(res.json).toHaveBeenCalledWith({
+      error: 'System tenant is not allowed for request-scoped routes',
+    });
+    expect(next).not.toHaveBeenCalled();
+  });
+
+  it('rejects blank server-resolved tenant IDs in strict mode', async () => {
+    process.env.TENANT_ISOLATION_STRICT = 'true';
+    _resetTenantMiddlewareStrictCache();
+
+    const req = mockTenantReq({ role: 'user' }, '   ');
+    const res = mockRes();
+    const next: NextFunction = jest.fn();
+
+    await restoreTenantContextFromReq(req, res, next);
+
+    expect(res.status).toHaveBeenCalledWith(403);
+    expect(res.json).toHaveBeenCalledWith(
+      expect.objectContaining({ error: expect.stringContaining('Tenant context required') }),
+    );
+    expect(next).not.toHaveBeenCalled();
+  });
+
   it('deletes uploaded temp files before rejecting system-tenant requests', async () => {
     const req = {
       ...mockReq({ tenantId: SYSTEM_TENANT_ID, role: 'user' }),
diff --git a/packages/api/src/middleware/preAuthTenant.spec.ts b/packages/api/src/middleware/preAuthTenant.spec.ts
index 669a43c84f..8aeb8b93ba 100644
--- a/packages/api/src/middleware/preAuthTenant.spec.ts
+++ b/packages/api/src/middleware/preAuthTenant.spec.ts
@@ -1,4 +1,4 @@
-import { getTenantId, logger } from '@librechat/data-schemas';
+import { getTenantId, getRequestId, logger } from '@librechat/data-schemas';
 import { preAuthTenantMiddleware } from './preAuthTenant';
 import type { Request, Response, NextFunction } from 'express';
 
@@ -54,6 +54,17 @@ describe('preAuthTenantMiddleware', () => {
     expect(capturedTenantId).toBe('acme-corp');
   });
 
+  it('propagates request ID from pre-auth routes', () => {
+    req.headers = { 'x-request-id': 'req-preauth' };
+    let capturedRequestId: string | undefined;
+    const capturedNext: NextFunction = () => {
+      capturedRequestId = getRequestId();
+    };
+
+    preAuthTenantMiddleware(req as Request, res as Response, capturedNext);
+    expect(capturedRequestId).toBe('req-preauth');
+  });
+
   it('ignores __SYSTEM__ sentinel and logs warning', () => {
     req.headers = { 'x-tenant-id': '__SYSTEM__' };
     req.ip = '10.0.0.1';
diff --git a/packages/api/src/middleware/preAuthTenant.ts b/packages/api/src/middleware/preAuthTenant.ts
index bab91f3a18..5d59cd8ae9 100644
--- a/packages/api/src/middleware/preAuthTenant.ts
+++ b/packages/api/src/middleware/preAuthTenant.ts
@@ -1,5 +1,6 @@
-import { tenantStorage, logger, SYSTEM_TENANT_ID } from '@librechat/data-schemas';
+import { logger, SYSTEM_TENANT_ID } from '@librechat/data-schemas';
 import type { Request, Response, NextFunction } from 'express';
+import { buildTenantContext, runWithTenantContext } from './tenant';
 
 /**
  * Pre-authentication tenant context middleware for unauthenticated routes.
@@ -27,46 +28,49 @@ import type { Request, Response, NextFunction } from 'express';
  * 3. Layer additional resolution on top (e.g., OpenID `tenant` claim → header).
  *
  * If no header is present, downstream runs without tenant ALS context (same as
- * single-tenant mode). This preserves backward compatibility.
+ * single-tenant mode), while request logging context can still propagate.
  */
 const MAX_TENANT_ID_LENGTH = 128;
 const VALID_TENANT_ID = /^[-a-zA-Z0-9_.]+$/;
 
 export function preAuthTenantMiddleware(req: Request, res: Response, next: NextFunction): void {
   const raw = req.headers['x-tenant-id'];
+  const requestContext = buildTenantContext({ headers: req.headers });
 
   if (!raw || typeof raw !== 'string') {
-    next();
+    runWithTenantContext(requestContext, next);
     return;
   }
 
   const tenantId = raw.trim();
 
   if (!tenantId) {
-    next();
+    runWithTenantContext(requestContext, next);
     return;
   }
 
   if (tenantId === SYSTEM_TENANT_ID) {
-    logger.warn('[preAuthTenant] Rejected __SYSTEM__ sentinel in X-Tenant-Id header', {
-      ip: req.ip,
-      path: req.path,
+    runWithTenantContext(requestContext, () => {
+      logger.warn('[preAuthTenant] Rejected __SYSTEM__ sentinel in X-Tenant-Id header', {
+        ip: req.ip,
+        path: req.path,
+      });
+      next();
     });
-    next();
     return;
   }
 
   if (tenantId.length > MAX_TENANT_ID_LENGTH || !VALID_TENANT_ID.test(tenantId)) {
-    logger.warn('[preAuthTenant] Rejected malformed X-Tenant-Id header', {
-      ip: req.ip,
-      length: tenantId.length,
-      path: req.path,
+    runWithTenantContext(requestContext, () => {
+      logger.warn('[preAuthTenant] Rejected malformed X-Tenant-Id header', {
+        ip: req.ip,
+        length: tenantId.length,
+        path: req.path,
+      });
+      next();
     });
-    next();
     return;
   }
 
-  return void tenantStorage.run({ tenantId }, async () => {
-    next();
-  });
+  runWithTenantContext(buildTenantContext({ headers: req.headers }, tenantId), next);
 }
diff --git a/packages/api/src/middleware/tenant.ts b/packages/api/src/middleware/tenant.ts
index d0907e0d65..41af195584 100644
--- a/packages/api/src/middleware/tenant.ts
+++ b/packages/api/src/middleware/tenant.ts
@@ -1,9 +1,26 @@
 import { unlink } from 'fs/promises';
 import { isMainThread } from 'worker_threads';
-import { getTenantId, tenantStorage, logger, SYSTEM_TENANT_ID } from '@librechat/data-schemas';
+import { tenantStorage, logger, SYSTEM_TENANT_ID } from '@librechat/data-schemas';
+import type { TenantContext } from '@librechat/data-schemas';
 import type { Response, NextFunction } from 'express';
 import type { ServerRequest } from '~/types/http';
 
+type ContextUser = {
+  tenantId?: string;
+  id?: string;
+  _id?: { toString: () => string };
+} | null;
+
+type ContextRequest = {
+  headers: ServerRequest['headers'];
+  tenantId?: string;
+  user?: ContextUser;
+  id?: string;
+  requestId?: string;
+};
+
+const REQUEST_ID_HEADERS = ['x-request-id', 'x-correlation-id'] as const;
+
 let _checkedThread = false;
 
 let _strictMode: boolean | undefined;
@@ -17,20 +34,73 @@ export function _resetTenantMiddlewareStrictCache(): void {
   _strictMode = undefined;
 }
 
+function normalizeContextValue(value?: string): string | undefined {
+  const trimmed = value?.trim();
+  return trimmed || undefined;
+}
+
+function getHeaderValue(value: string | string[] | undefined): string | undefined {
+  return normalizeContextValue(Array.isArray(value) ? value[0] : value);
+}
+
+function getRequestId(req: ContextRequest): string | undefined {
+  const requestId = normalizeContextValue(req.requestId) ?? normalizeContextValue(req.id);
+  if (requestId) {
+    return requestId;
+  }
+  for (const header of REQUEST_ID_HEADERS) {
+    const value = getHeaderValue(req.headers[header]);
+    if (value) {
+      return value;
+    }
+  }
+  return undefined;
+}
+
+function getUserId(user: ContextUser): string | undefined {
+  return normalizeContextValue(user?.id) ?? normalizeContextValue(user?._id?.toString());
+}
+
+function hasTenantContext(context: TenantContext): boolean {
+  return Boolean(context.tenantId || context.userId || context.requestId);
+}
+
+export function buildTenantContext(
+  req: ContextRequest,
+  tenantId = req.tenantId ?? req.user?.tenantId,
+): TenantContext {
+  return {
+    tenantId: normalizeContextValue(tenantId),
+    userId: getUserId(req.user ?? null),
+    requestId: getRequestId(req),
+  };
+}
+
+export function runWithTenantContext(context: TenantContext, next: NextFunction): void {
+  if (!hasTenantContext(context)) {
+    next();
+    return;
+  }
+  return void tenantStorage.run(context, async () => {
+    next();
+  });
+}
+
 /**
  * Express middleware that propagates the authenticated user's `tenantId` into
- * the AsyncLocalStorage context used by the Mongoose tenant-isolation plugin.
+ * the AsyncLocalStorage context used by the Mongoose tenant-isolation plugin
+ * and request-scoped logging.
  *
  * **Placement**: Chained automatically by `requireJwtAuth` after successful
  * passport authentication (req.user is populated). Must NOT be registered at
  * global `app.use()` scope — `req.user` is undefined at that stage.
  *
  * Behaviour:
- * - Authenticated request with `tenantId` → wraps downstream in `tenantStorage.run({ tenantId })`
+ * - Authenticated request with context → wraps downstream in `tenantStorage.run(context)`
  * - Authenticated request **without** `tenantId`:
  *   - Strict mode (`TENANT_ISOLATION_STRICT=true`) → responds 403
- *   - Non-strict (default) → passes through without ALS context (backward compat)
- * - Unauthenticated request → no-op (calls `next()` directly)
+ *   - Non-strict (default) → passes through with user/request context only
+ * - Unauthenticated request → propagates request context when available
  */
 export function tenantContextMiddleware(
   req: ServerRequest,
@@ -47,27 +117,26 @@ export function tenantContextMiddleware(
     }
   }
 
-  const user = req.user as { tenantId?: string } | undefined;
+  const user = req.user;
+  const context = buildTenantContext(req);
 
   if (!user) {
-    next();
+    runWithTenantContext(context, next);
     return;
   }
 
-  const tenantId = user.tenantId;
+  const { tenantId } = context;
 
   if (!tenantId) {
     if (isStrict()) {
       res.status(403).json({ error: 'Tenant context required in strict isolation mode' });
       return;
     }
-    next();
+    runWithTenantContext(context, next);
     return;
   }
 
-  return void tenantStorage.run({ tenantId }, async () => {
-    next();
-  });
+  runWithTenantContext(context, next);
 }
 
 export type RequestTenantSource = {
@@ -137,6 +206,19 @@ async function rejectRequestWithUploadCleanup(
   res.status(403).json({ error: message });
 }
 
+function rejectRequestWithUploadCleanupInContext(
+  context: TenantContext,
+  req: ServerRequest,
+  res: Response,
+  message: string,
+): Promise<void> {
+  const rejectRequest = () => rejectRequestWithUploadCleanup(req, res, message);
+  if (!hasTenantContext(context)) {
+    return rejectRequest();
+  }
+  return tenantStorage.run(context, rejectRequest);
+}
+
 /**
  * Re-enters tenant ALS from the server-resolved request tenant.
  *
@@ -150,20 +232,23 @@ export function restoreTenantContextFromReq(
   next: NextFunction,
 ): void | Promise<void> {
   const tenantId = resolveRequestTenantId(req as RequestTenantSource);
+  const context = buildTenantContext(req, tenantId);
+  const resolvedTenantId = context.tenantId;
 
-  if (!tenantId) {
+  if (!resolvedTenantId) {
     if (isStrict()) {
-      return rejectRequestWithUploadCleanup(
+      return rejectRequestWithUploadCleanupInContext(
+        context,
         req,
         res,
         'Tenant context required in strict isolation mode',
       );
     }
-    next();
+    runWithTenantContext(context, next);
     return;
   }
 
-  if (tenantId === SYSTEM_TENANT_ID) {
+  if (resolvedTenantId === SYSTEM_TENANT_ID) {
     logger.warn('[restoreTenantContextFromReq] Rejected system tenant for request route', {
       path: req.path,
     });
@@ -174,12 +259,15 @@ export function restoreTenantContextFromReq(
     );
   }
 
-  if (getTenantId() === tenantId) {
+  const currentContext = tenantStorage.getStore();
+  if (
+    currentContext?.tenantId === context.tenantId &&
+    currentContext?.userId === context.userId &&
+    currentContext?.requestId === context.requestId
+  ) {
     next();
     return;
   }
 
-  return void tenantStorage.run({ tenantId }, async () => {
-    next();
-  });
+  return runWithTenantContext(context, next);
 }
diff --git a/packages/data-schemas/src/config/parsers.spec.ts b/packages/data-schemas/src/config/parsers.spec.ts
new file mode 100644
index 0000000000..188f42db3c
--- /dev/null
+++ b/packages/data-schemas/src/config/parsers.spec.ts
@@ -0,0 +1,73 @@
+import { debugTraverse } from './parsers';
+
+const SPLAT_SYMBOL = Symbol.for('splat');
+const MESSAGE_SYMBOL = Symbol.for('message');
+
+type FormatterInfo = Record<string | symbol, unknown> & {
+  level: string;
+  message: string;
+  timestamp: string;
+};
+
+function runFormatter(info: FormatterInfo): string {
+  const transformed = debugTraverse.transform(info);
+  if (transformed && typeof transformed === 'object') {
+    const message = (transformed as Record<string | symbol, unknown>)[MESSAGE_SYMBOL];
+    return typeof message === 'string' ? message : String(transformed);
+  }
+  return String(transformed);
+}
+
+function buildInfo(level: string, meta: Record<string, unknown>): FormatterInfo {
+  return {
+    level,
+    message: 'test',
+    timestamp: 'ts',
+    ...meta,
+    [SPLAT_SYMBOL]: [meta],
+  };
+}
+
+describe('debugTraverse request context', () => {
+  it('appends request context metadata for non-debug lines', () => {
+    const out = runFormatter(
+      buildInfo('info', {
+        tenantId: 'tenant-1',
+        userId: 'user-1',
+        requestId: 'req-1',
+      }),
+    );
+
+    expect(out).toContain('"tenantId":"tenant-1"');
+    expect(out).toContain('"userId":"user-1"');
+    expect(out).toContain('"requestId":"req-1"');
+  });
+
+  it('does not append the system tenant sentinel as tenantId', () => {
+    const out = runFormatter(
+      buildInfo('info', {
+        tenantId: '__SYSTEM__',
+        userId: 'user-1',
+        requestId: 'req-1',
+      }),
+    );
+
+    expect(out).not.toContain('__SYSTEM__');
+    expect(out).not.toContain('"tenantId"');
+    expect(out).toContain('"userId":"user-1"');
+    expect(out).toContain('"requestId":"req-1"');
+  });
+
+  it('omits the system tenant sentinel from debug object metadata', () => {
+    const out = runFormatter(
+      buildInfo('debug', {
+        tenantId: '__SYSTEM__',
+        userId: 'user-1',
+      }),
+    );
+
+    expect(out).not.toContain('__SYSTEM__');
+    expect(out).not.toMatch(/tenantId:/);
+    expect(out).toContain('userId');
+  });
+});
diff --git a/packages/data-schemas/src/config/parsers.ts b/packages/data-schemas/src/config/parsers.ts
index 80dd9b767c..e21927a72b 100644
--- a/packages/data-schemas/src/config/parsers.ts
+++ b/packages/data-schemas/src/config/parsers.ts
@@ -1,6 +1,7 @@
 import { klona } from 'klona';
 import winston from 'winston';
 import traverse from '../utils/object-traverse';
+import { SYSTEM_TENANT_ID } from './tenantContext';
 import type { TraverseContext } from '../utils/object-traverse';
 
 const SPLAT_SYMBOL = Symbol.for('splat');
@@ -8,6 +9,7 @@ const MESSAGE_SYMBOL = Symbol.for('message');
 const CONSOLE_JSON_STRING_LENGTH: number =
   parseInt(process.env.CONSOLE_JSON_STRING_LENGTH || '', 10) || 255;
 const DEBUG_MESSAGE_LENGTH: number = parseInt(process.env.DEBUG_MESSAGE_LENGTH || '', 10) || 150;
+const LOG_CONTEXT_KEYS = ['tenantId', 'userId', 'requestId'] as const;
 
 const sensitiveKeys: RegExp[] = [
   /^(sk-)[^\s]+/, // OpenAI API key pattern
@@ -104,6 +106,25 @@ const condenseArray = (item: unknown): string | unknown => {
   return item;
 };
 
+function formatRequestContext(metadata: Record<string, unknown>): string {
+  const context: Partial<Record<(typeof LOG_CONTEXT_KEYS)[number], string>> = {};
+  LOG_CONTEXT_KEYS.forEach((key) => {
+    const value = metadata[key];
+    if (key === 'tenantId' && value === SYSTEM_TENANT_ID) {
+      return;
+    }
+    if (typeof value === 'string' && value) {
+      context[key] = value;
+    }
+  });
+  return Object.keys(context).length > 0 ? JSON.stringify(context) : '';
+}
+
+function appendRequestContext(line: string, metadata: Record<string, unknown>): string {
+  const context = formatRequestContext(metadata);
+  return context ? `${line} ${context}` : line;
+}
+
 /**
  * Formats log messages for debugging purposes.
  * - Truncates long strings within log messages.
@@ -131,7 +152,7 @@ const debugTraverse = winston.format.printf(
 
     try {
       if (level !== 'debug') {
-        return msgParts[0];
+        return appendRequestContext(msgParts[0], metadata);
       }
 
       if (!metadata) {
@@ -144,22 +165,25 @@ const debugTraverse = winston.format.printf(
       const debugValue = Array.isArray(splatArray) ? splatArray[0] : undefined;
 
       if (!debugValue) {
-        return msgParts[0];
+        return appendRequestContext(msgParts[0], metadata);
       }
 
       if (debugValue && Array.isArray(debugValue)) {
         msgParts.push(`\n${JSON.stringify(debugValue.map(condenseArray))}`);
-        return msgParts.join('');
+        return appendRequestContext(msgParts.join(''), metadata);
       }
 
       if (typeof debugValue !== 'object') {
         msgParts.push(` ${debugValue}`);
-        return msgParts.join('');
+        return appendRequestContext(msgParts.join(''), metadata);
       }
 
       msgParts.push('\n{');
 
       const copy = klona(metadata);
+      if (copy.tenantId === SYSTEM_TENANT_ID) {
+        delete copy.tenantId;
+      }
       try {
         const traversal = traverse(copy);
         traversal.forEach(function (this: TraverseContext, value: unknown) {
diff --git a/packages/data-schemas/src/config/tenantContext.spec.ts b/packages/data-schemas/src/config/tenantContext.spec.ts
index 7e6cc0748d..a01e01ff76 100644
--- a/packages/data-schemas/src/config/tenantContext.spec.ts
+++ b/packages/data-schemas/src/config/tenantContext.spec.ts
@@ -1,4 +1,4 @@
-import { tenantStorage, runAsSystem, scopedCacheKey } from './tenantContext';
+import { tenantStorage, getUserId, getRequestId, runAsSystem, scopedCacheKey } from './tenantContext';
 
 describe('scopedCacheKey', () => {
   it('returns base key when no ALS context is set', () => {
@@ -23,4 +23,21 @@ describe('scopedCacheKey', () => {
     });
     expect(scopedCacheKey('KEY')).toBe('KEY');
   });
+
+  it('reads user and request IDs from ALS context', async () => {
+    await tenantStorage.run({ userId: 'user-1', requestId: 'req-1' }, async () => {
+      expect(getUserId()).toBe('user-1');
+      expect(getRequestId()).toBe('req-1');
+    });
+  });
+
+  it('preserves user and request context inside system tenant operations', async () => {
+    await tenantStorage.run({ tenantId: 'acme', userId: 'user-1', requestId: 'req-1' }, async () => {
+      await runAsSystem(async () => {
+        expect(getUserId()).toBe('user-1');
+        expect(getRequestId()).toBe('req-1');
+        expect(scopedCacheKey('KEY')).toBe('KEY');
+      });
+    });
+  });
 });
diff --git a/packages/data-schemas/src/config/tenantContext.ts b/packages/data-schemas/src/config/tenantContext.ts
index eb77edb27d..9dc73f972b 100644
--- a/packages/data-schemas/src/config/tenantContext.ts
+++ b/packages/data-schemas/src/config/tenantContext.ts
@@ -2,6 +2,8 @@ import { AsyncLocalStorage } from 'async_hooks';
 
 export interface TenantContext {
   tenantId?: string;
+  userId?: string;
+  requestId?: string;
 }
 
 /** Sentinel value for deliberate cross-tenant system operations */
@@ -19,12 +21,23 @@ export function getTenantId(): string | undefined {
   return tenantStorage.getStore()?.tenantId;
 }
 
+/** Returns the current user ID from async context, or undefined if none is set */
+export function getUserId(): string | undefined {
+  return tenantStorage.getStore()?.userId;
+}
+
+/** Returns the current request ID from async context, or undefined if none is set */
+export function getRequestId(): string | undefined {
+  return tenantStorage.getStore()?.requestId;
+}
+
 /**
  * Runs a function in an explicit cross-tenant system context (bypasses tenant filtering).
  * The callback MUST be async — sync callbacks returning Mongoose thenables will lose context.
  */
 export function runAsSystem<T>(fn: () => Promise<T>): Promise<T> {
-  return tenantStorage.run({ tenantId: SYSTEM_TENANT_ID }, fn);
+  const { requestId, userId } = tenantStorage.getStore() ?? {};
+  return tenantStorage.run({ tenantId: SYSTEM_TENANT_ID, requestId, userId }, fn);
 }
 
 /**
diff --git a/packages/data-schemas/src/config/winston.ts b/packages/data-schemas/src/config/winston.ts
index 24a2c6c987..9bc7652415 100644
--- a/packages/data-schemas/src/config/winston.ts
+++ b/packages/data-schemas/src/config/winston.ts
@@ -1,6 +1,7 @@
 import winston from 'winston';
 import 'winston-daily-rotate-file';
 import { redactFormat, redactMessage, debugTraverse, jsonTruncateFormat } from './parsers';
+import { getTenantId, getUserId, getRequestId, SYSTEM_TENANT_ID } from './tenantContext';
 import { getLogDirectory } from './utils';
 
 const logDir = getLogDirectory();
@@ -24,6 +25,49 @@ const levels: winston.config.AbstractConfigSetLevels = {
   silly: 7,
 };
 
+const LOG_CONTEXT_KEYS = ['tenantId', 'userId', 'requestId'] as const;
+
+function getLogTenantId(): string | undefined {
+  const tenantId = getTenantId();
+  return tenantId === SYSTEM_TENANT_ID ? undefined : tenantId;
+}
+
+const requestContextFormat = winston.format((info: winston.Logform.TransformableInfo) => {
+  if (info.tenantId === SYSTEM_TENANT_ID) {
+    delete info.tenantId;
+  }
+  const context = {
+    tenantId: getLogTenantId(),
+    userId: getUserId(),
+    requestId: getRequestId(),
+  };
+  LOG_CONTEXT_KEYS.forEach((key) => {
+    if (context[key] && info[key] == null) {
+      info[key] = context[key];
+    }
+  });
+  return info;
+});
+
+function formatRequestContext(info: winston.Logform.TransformableInfo): string {
+  const context: Partial<Record<(typeof LOG_CONTEXT_KEYS)[number], string>> = {};
+  LOG_CONTEXT_KEYS.forEach((key) => {
+    const value = info[key];
+    if (key === 'tenantId' && value === SYSTEM_TENANT_ID) {
+      return;
+    }
+    if (typeof value === 'string' && value) {
+      context[key] = value;
+    }
+  });
+  return Object.keys(context).length > 0 ? JSON.stringify(context) : '';
+}
+
+function appendRequestContext(line: string, info: winston.Logform.TransformableInfo): string {
+  const context = formatRequestContext(info);
+  return context ? `${line} ${context}` : line;
+}
+
 winston.addColors({
   info: 'green',
   warn: 'italic yellow',
@@ -41,6 +85,7 @@ const fileFormat = winston.format.combine(
   winston.format.timestamp({ format: () => new Date().toISOString() }),
   winston.format.errors({ stack: true }),
   winston.format.splat(),
+  requestContextFormat(),
 );
 
 const transports: winston.transport[] = [
@@ -71,11 +116,13 @@ if (useDebugLogging) {
 
 const consoleFormat = winston.format.combine(
   redactFormat(),
+  requestContextFormat(),
   winston.format.colorize({ all: true }),
   winston.format.timestamp({ format: 'YYYY-MM-DD HH:mm:ss' }),
   winston.format.printf((info) => {
     const message = `${info.timestamp} ${info.level}: ${info.message}`;
-    return info.level.includes('error') ? redactMessage(message) : message;
+    const line = appendRequestContext(message, info);
+    return info.level.includes('error') ? redactMessage(line) : line;
   }),
 );
 
diff --git a/packages/data-schemas/src/index.ts b/packages/data-schemas/src/index.ts
index 4156559658..8c95d7f9cc 100644
--- a/packages/data-schemas/src/index.ts
+++ b/packages/data-schemas/src/index.ts
@@ -23,6 +23,8 @@ export { default as meiliLogger } from './config/meiliLogger';
 export {
   tenantStorage,
   getTenantId,
+  getUserId,
+  getRequestId,
   runAsSystem,
   scopedCacheKey,
   SYSTEM_TENANT_ID,