diff --git a/src/khoj/configure.py b/src/khoj/configure.py
index 717ad859..4bb23812 100644
--- a/src/khoj/configure.py
+++ b/src/khoj/configure.py
@@ -77,17 +77,18 @@ class UserAuthenticationBackend(AuthenticationBackend):
                 .afirst()
             )
             if user:
-                if state.billing_enabled:
-                    subscription_state = await aget_user_subscription_state(user)
-                    subscribed = (
-                        subscription_state == SubscriptionState.SUBSCRIBED.value
-                        or subscription_state == SubscriptionState.TRIAL.value
-                        or subscription_state == SubscriptionState.UNSUBSCRIBED.value
-                    )
-                    if subscribed:
-                        return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user)
-                    return AuthCredentials(["authenticated"]), AuthenticatedKhojUser(user)
-                return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user)
+                if not state.billing_enabled:
+                    return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user)
+
+                subscription_state = await aget_user_subscription_state(user)
+                subscribed = (
+                    subscription_state == SubscriptionState.SUBSCRIBED.value
+                    or subscription_state == SubscriptionState.TRIAL.value
+                    or subscription_state == SubscriptionState.UNSUBSCRIBED.value
+                )
+                if subscribed:
+                    return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user)
+                return AuthCredentials(["authenticated"]), AuthenticatedKhojUser(user)
         if len(request.headers.get("Authorization", "").split("Bearer ")) == 2:
             # Get bearer token from header
             bearer_token = request.headers["Authorization"].split("Bearer ")[1]
@@ -99,19 +100,18 @@ class UserAuthenticationBackend(AuthenticationBackend):
                 .afirst()
             )
             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
-                        or subscription_state == SubscriptionState.TRIAL.value
-                        or subscription_state == SubscriptionState.UNSUBSCRIBED.value
-                    )
-                    if subscribed:
-                        return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(
-                            user_with_token.user
-                        )
-                    return AuthCredentials(["authenticated"]), AuthenticatedKhojUser(user_with_token.user)
-                return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user_with_token.user)
+                if not state.billing_enabled:
+                    return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user_with_token.user)
+
+                subscription_state = await aget_user_subscription_state(user_with_token.user)
+                subscribed = (
+                    subscription_state == SubscriptionState.SUBSCRIBED.value
+                    or subscription_state == SubscriptionState.TRIAL.value
+                    or subscription_state == SubscriptionState.UNSUBSCRIBED.value
+                )
+                if subscribed:
+                    return AuthCredentials(["authenticated", "premium"]), AuthenticatedKhojUser(user_with_token.user)
+                return AuthCredentials(["authenticated"]), AuthenticatedKhojUser(user_with_token.user)
         if state.anonymous_mode:
             user = await self.khojuser_manager.filter(username="default").prefetch_related("subscription").afirst()
             if user:
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index 7efd8bfd..65516a9c 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -46,6 +46,7 @@ from khoj.routers.helpers import (
     is_ready_to_chat,
     update_telemetry_state,
     validate_conversation_config,
+    ConversationCommandRateLimiter,
 )
 from khoj.search_filter.date_filter import DateFilter
 from khoj.search_filter.file_filter import FileFilter
@@ -67,6 +68,7 @@ from khoj.utils.state import SearchType
 # Initialize Router
 api = APIRouter()
 logger = logging.getLogger(__name__)
+conversation_command_rate_limiter = ConversationCommandRateLimiter(trial_rate_limit=5, subscribed_rate_limit=100)
 
 
 def map_config_to_object(content_source: str):
@@ -670,6 +672,8 @@ async def chat(
     await is_ready_to_chat(user)
     conversation_command = get_conversation_command(query=q, any_references=True)
 
+    conversation_command_rate_limiter.update_and_check_if_valid(request, conversation_command)
+
     q = q.replace(f"/{conversation_command.value}", "").strip()
 
     meta_log = (await ConversationAdapters.aget_conversation_by_user(user)).conversation_log
diff --git a/src/khoj/routers/helpers.py b/src/khoj/routers/helpers.py
index 4e883f35..56fba861 100644
--- a/src/khoj/routers/helpers.py
+++ b/src/khoj/routers/helpers.py
@@ -300,6 +300,40 @@ class ApiUserRateLimiter:
         user_requests.append(time())
 
 
+class ConversationCommandRateLimiter:
+    def __init__(self, trial_rate_limit: int, subscribed_rate_limit: int):
+        self.cache = defaultdict(lambda: defaultdict(list))
+        self.trial_rate_limit = trial_rate_limit
+        self.subscribed_rate_limit = subscribed_rate_limit
+        self.restricted_commands = [ConversationCommand.Online, ConversationCommand.Image]
+
+    def update_and_check_if_valid(self, request: Request, conversation_command: ConversationCommand):
+        if state.billing_enabled is False:
+            return
+
+        if not request.user.is_authenticated:
+            return
+
+        if conversation_command not in self.restricted_commands:
+            return
+
+        user: KhojUser = request.user.object
+        user_cache = self.cache[user.uuid]
+        subscribed = has_required_scope(request, ["premium"])
+        user_cache[conversation_command].append(time())
+
+        # Remove requests outside of the 24-hr time window
+        cutoff = time() - 60 * 60 * 24
+        while user_cache[conversation_command] and user_cache[conversation_command][0] < cutoff:
+            user_cache[conversation_command].pop(0)
+
+        if subscribed and len(user_cache[conversation_command]) > self.subscribed_rate_limit:
+            raise HTTPException(status_code=429, detail="Too Many Requests")
+        if not subscribed and len(user_cache[conversation_command]) > self.trial_rate_limit:
+            raise HTTPException(status_code=429, detail="Too Many Requests. Subscribe to increase your rate limit.")
+        return
+
+
 class ApiIndexedDataLimiter:
     def __init__(
         self,