diff --git a/src/web-server/middleware/auth-middleware.ts b/src/web-server/middleware/auth-middleware.ts
index 28c12d2b..248e303c 100644
--- a/src/web-server/middleware/auth-middleware.ts
+++ b/src/web-server/middleware/auth-middleware.ts
@@ -56,8 +56,9 @@ function getSessionSecret(): string {
       fs.mkdirSync(dir, { recursive: true });
     }
     fs.writeFileSync(SESSION_SECRET_PATH, newSecret, { mode: 0o600 });
-  } catch {
-    // If we can't persist, still return the secret for this session
+  } catch (err) {
+    // Log warning - sessions won't persist across restarts
+    console.warn('[!] Failed to persist session secret:', (err as Error).message);
   }
 
   return newSecret;
diff --git a/src/web-server/routes/auth-routes.ts b/src/web-server/routes/auth-routes.ts
index a29ff6ce..3a7efb3b 100644
--- a/src/web-server/routes/auth-routes.ts
+++ b/src/web-server/routes/auth-routes.ts
@@ -5,9 +5,23 @@
 
 import { Router, type Request, type Response } from 'express';
 import bcrypt from 'bcrypt';
+import crypto from 'crypto';
 import { getDashboardAuthConfig } from '../../config/unified-config-loader';
 import { loginRateLimiter } from '../middleware/auth-middleware';
 
+/**
+ * Timing-safe string comparison to prevent timing attacks.
+ * Returns true if strings match, false otherwise.
+ */
+function timingSafeEqual(a: string, b: string): boolean {
+  if (a.length !== b.length) {
+    // Still compare to avoid length-based timing leak
+    crypto.timingSafeEqual(Buffer.from(a), Buffer.from(a));
+    return false;
+  }
+  return crypto.timingSafeEqual(Buffer.from(a), Buffer.from(b));
+}
+
 const router = Router();
 
 /**
@@ -38,8 +52,8 @@ router.post('/login', loginRateLimiter, async (req: Request, res: Response) => {
     return;
   }
 
-  // Verify credentials
-  const usernameMatch = username === authConfig.username;
+  // Verify credentials (timing-safe comparison for username)
+  const usernameMatch = timingSafeEqual(username, authConfig.username);
   const passwordMatch = await bcrypt.compare(password, authConfig.password_hash);
 
   if (!usernameMatch || !passwordMatch) {
@@ -47,11 +61,16 @@ router.post('/login', loginRateLimiter, async (req: Request, res: Response) => {
     return;
   }
 
-  // Set session
-  req.session.authenticated = true;
-  req.session.username = username;
-
-  res.json({ success: true, username });
+  // Regenerate session to prevent session fixation, then set auth
+  req.session.regenerate((err) => {
+    if (err) {
+      res.status(500).json({ error: 'Session error' });
+      return;
+    }
+    req.session.authenticated = true;
+    req.session.username = username;
+    res.json({ success: true, username });
+  });
 });
 
 /**