diff --git a/src/khoj/configure.py b/src/khoj/configure.py
index 19c1fd81..fc64af0f 100644
--- a/src/khoj/configure.py
+++ b/src/khoj/configure.py
@@ -77,7 +77,10 @@ class UserAuthenticationBackend(AuthenticationBackend):
             if user:
                 if state.billing_enabled:
                     subscription_state = await aget_user_subscription_state(user)
-                    subscribed = subscription_state == SubscriptionState.SUBSCRIBED.value
+                    subscribed = (
+                        subscription_state == SubscriptionState.SUBSCRIBED.value
+                        or subscription_state == SubscriptionState.TRIAL.value
+                    )
                     if subscribed:
                         return AuthCredentials(["authenticated", "subscribed"]), AuthenticatedKhojUser(
                             user_with_token.user
@@ -97,7 +100,10 @@ class UserAuthenticationBackend(AuthenticationBackend):
             if user_with_token:
                 if state.billing_enabled:
                     subscription_state = await aget_user_subscription_state(user_with_token.user)
-                    subscribed = subscription_state == SubscriptionState.SUBSCRIBED.value
+                    subscribed = (
+                        subscription_state == SubscriptionState.SUBSCRIBED.value
+                        or subscription_state == SubscriptionState.TRIAL.value
+                    )
                     if subscribed:
                         return AuthCredentials(["authenticated", "subscribed"]), AuthenticatedKhojUser(
                             user_with_token.user
diff --git a/src/khoj/database/adapters/__init__.py b/src/khoj/database/adapters/__init__.py
index 146de11c..7f76b796 100644
--- a/src/khoj/database/adapters/__init__.py
+++ b/src/khoj/database/adapters/__init__.py
@@ -1,7 +1,7 @@
 import math
 import random
 import secrets
-from datetime import date, datetime, timezone
+from datetime import date, datetime, timezone, timedelta
 from typing import List, Optional, Type
 from enum import Enum
 
@@ -140,6 +140,10 @@ def subscription_to_state(subscription: Subscription) -> str:
     if not subscription:
         return SubscriptionState.INVALID.value
     elif subscription.type == Subscription.Type.TRIAL:
+        # Trial subscription is valid for 7 days
+        if datetime.now(tz=timezone.utc) - subscription.created_at > timedelta(days=7):
+            return SubscriptionState.EXPIRED.value
+
         return SubscriptionState.TRIAL.value
     elif subscription.is_recurring and subscription.renewal_date >= datetime.now(tz=timezone.utc):
         return SubscriptionState.SUBSCRIBED.value