diff --git a/src/khoj/configure.py b/src/khoj/configure.py
index 6aa747e8..bff7e3ca 100644
--- a/src/khoj/configure.py
+++ b/src/khoj/configure.py
@@ -80,6 +80,7 @@ class UserAuthenticationBackend(AuthenticationBackend):
                     subscribed = (
                         subscription_state == SubscriptionState.SUBSCRIBED.value
                         or subscription_state == SubscriptionState.TRIAL.value
+                        or subscription_state == SubscriptionState.UNSUBSCRIBED.value
                     )
                     if subscribed:
                         return AuthCredentials(["authenticated", "subscribed"]), AuthenticatedKhojUser(user)
@@ -101,6 +102,7 @@ class UserAuthenticationBackend(AuthenticationBackend):
                     subscribed = (
                         subscription_state == SubscriptionState.SUBSCRIBED.value
                         or subscription_state == SubscriptionState.TRIAL.value
+                        or subscription_state == SubscriptionState.UNSUBSCRIBED.value
                     )
                     if subscribed:
                         return AuthCredentials(["authenticated", "subscribed"]), AuthenticatedKhojUser(
diff --git a/src/khoj/database/adapters/__init__.py b/src/khoj/database/adapters/__init__.py
index 7f76b796..bcf4856c 100644
--- a/src/khoj/database/adapters/__init__.py
+++ b/src/khoj/database/adapters/__init__.py
@@ -1,6 +1,7 @@
 import math
 import random
 import secrets
+import sys
 from datetime import date, datetime, timezone, timedelta
 from typing import List, Optional, Type
 from enum import Enum
@@ -474,6 +475,12 @@ class EntryAdapters:
     async def adelete_all_entries(user: KhojUser):
         return await Entry.objects.filter(user=user).adelete()
 
+    @staticmethod
+    def get_size_of_indexed_data_in_mb(user: KhojUser):
+        entries = Entry.objects.filter(user=user).iterator()
+        total_size = sum(sys.getsizeof(entry.compiled) for entry in entries)
+        return total_size / 1024 / 1024
+
     @staticmethod
     def apply_filters(user: KhojUser, query: str, file_type_filter: str = None):
         q_filter_terms = Q()
diff --git a/src/khoj/interface/web/config.html b/src/khoj/interface/web/config.html
index 318759df..88fbc70d 100644
--- a/src/khoj/interface/web/config.html
+++ b/src/khoj/interface/web/config.html
@@ -4,6 +4,7 @@
 <div class="page">
     <div id="content" class="section">
         <h2 class="section-title">Content</h2>
+        <p id="indexed-data-size" class="card-description">{{indexed_data_size_in_mb}} MB used</p>
         <div class="section-cards">
             <div class="card">
                 <div class="card-title-row">
@@ -171,7 +172,7 @@
             </div>
         </div>
     </div>
-    {% if not billing_enabled %}
+    {% if billing_enabled %}
     <div id="billing" class="section">
         <h2 class="section-title">Billing</h2>
         <div class="section-cards">
@@ -191,7 +192,7 @@
                     <p id="trial-description"
                        class="card-description"
                        style="display: {% if subscription_state != 'trial' %}none{% endif %}">
-                        Subscribe to Khoj Cloud
+                        Subscribe to Khoj Cloud. See <a href="https://khoj.dev/pricing">pricing</a> for details.
                     </p>
                     <p id="unsubscribe-description"
                        class="card-description"
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index f1967e67..56d9f313 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -9,10 +9,10 @@ from typing import Any, Dict, List, Optional, Union
 from asgiref.sync import sync_to_async
 
 # External Packages
-from fastapi import APIRouter, Depends, Header, HTTPException, Request
+from fastapi import APIRouter, Depends, HTTPException, Request
 from fastapi.requests import Request
 from fastapi.responses import Response, StreamingResponse
-from starlette.authentication import requires, has_required_scope
+from starlette.authentication import requires
 
 # Internal Packages
 from khoj.configure import configure_server
diff --git a/src/khoj/routers/helpers.py b/src/khoj/routers/helpers.py
index dbcef1bc..273de15b 100644
--- a/src/khoj/routers/helpers.py
+++ b/src/khoj/routers/helpers.py
@@ -9,11 +9,12 @@ from functools import partial
 from time import time
 from typing import Annotated, Any, Dict, Iterator, List, Optional, Tuple, Union
 
-# External Packages
-from fastapi import Depends, Header, HTTPException, Request
+from fastapi import Depends, Header, HTTPException, Request, UploadFile
 from starlette.authentication import has_required_scope
+from asgiref.sync import sync_to_async
 
-from khoj.database.adapters import ConversationAdapters
+
+from khoj.database.adapters import ConversationAdapters, EntryAdapters
 from khoj.database.models import KhojUser, Subscription
 from khoj.processor.conversation import prompts
 from khoj.processor.conversation.gpt4all.chat_model import converse_offline, send_message_to_model_offline
@@ -297,6 +298,60 @@ class ApiUserRateLimiter:
         user_requests.append(time())
 
 
+class ApiIndexedDataLimiter:
+    def __init__(
+        self,
+        incoming_entries_size_limit: float,
+        subscribed_incoming_entries_size_limit: float,
+        total_entries_size_limit: float,
+        subscribed_total_entries_size_limit: float,
+    ):
+        self.num_entries_size = incoming_entries_size_limit
+        self.subscribed_num_entries_size = subscribed_incoming_entries_size_limit
+        self.total_entries_size_limit = total_entries_size_limit
+        self.subscribed_total_entries_size = subscribed_total_entries_size_limit
+
+    def __call__(self, request: Request, files: List[UploadFile]):
+        if state.billing_enabled is False:
+            return
+        subscribed = has_required_scope(request, ["subscribed"])
+        incoming_data_size_mb = 0
+        deletion_file_names = set()
+
+        if not request.user.is_authenticated:
+            return
+
+        user: KhojUser = request.user.object
+
+        for file in files:
+            if file.size == 0:
+                deletion_file_names.add(file.filename)
+
+            incoming_data_size_mb += file.size / 1024 / 1024
+
+        num_deleted_entries = 0
+        for file_path in deletion_file_names:
+            deleted_count = EntryAdapters.delete_entry_by_file(user, file_path)
+            num_deleted_entries += deleted_count
+
+        logger.info(f"Deleted {num_deleted_entries} entries for user: {user}.")
+
+        if subscribed and incoming_data_size_mb >= self.subscribed_num_entries_size:
+            raise HTTPException(status_code=429, detail="Too much data indexed.")
+        if not subscribed and incoming_data_size_mb >= self.num_entries_size:
+            raise HTTPException(
+                status_code=429, detail="Too much data indexed. Subscribe to increase your data index limit."
+            )
+
+        user_size_data = EntryAdapters.get_size_of_indexed_data_in_mb(user)
+        if subscribed and user_size_data + incoming_data_size_mb >= self.subscribed_total_entries_size:
+            raise HTTPException(status_code=429, detail="Too much data indexed.")
+        if not subscribed and user_size_data + incoming_data_size_mb >= self.total_entries_size_limit:
+            raise HTTPException(
+                status_code=429, detail="Too much data indexed. Subscribe to increase your data index limit."
+            )
+
+
 class CommonQueryParamsClass:
     def __init__(
         self,
diff --git a/src/khoj/routers/indexer.py b/src/khoj/routers/indexer.py
index 0432eed0..0c906707 100644
--- a/src/khoj/routers/indexer.py
+++ b/src/khoj/routers/indexer.py
@@ -2,7 +2,7 @@ import asyncio
 import logging
 from typing import Dict, Optional, Union
 
-from fastapi import APIRouter, Header, Request, Response, UploadFile
+from fastapi import APIRouter, Header, Request, Response, UploadFile, Depends
 from pydantic import BaseModel
 from starlette.authentication import requires
 
@@ -18,6 +18,7 @@ from khoj.search_type import image_search, text_search
 from khoj.utils import constants, state
 from khoj.utils.config import ContentIndex, SearchModels
 from khoj.utils.helpers import LRU, get_file_type
+from khoj.routers.helpers import ApiIndexedDataLimiter
 from khoj.utils.rawconfig import ContentConfig, FullConfig, SearchConfig
 from khoj.utils.yaml import save_config_to_file_updated_state
 
@@ -53,6 +54,14 @@ async def update(
     user_agent: Optional[str] = Header(None),
     referer: Optional[str] = Header(None),
     host: Optional[str] = Header(None),
+    indexed_data_limiter: ApiIndexedDataLimiter = Depends(
+        ApiIndexedDataLimiter(
+            incoming_entries_size_limit=10,
+            subscribed_incoming_entries_size_limit=25,
+            total_entries_size_limit=10,
+            subscribed_total_entries_size_limit=100,
+        )
+    ),
 ):
     user = request.user.object
     try:
@@ -92,7 +101,7 @@ async def update(
             logger.info("📬 Initializing content index on first run.")
             default_full_config = FullConfig(
                 content_type=None,
-                search_type=SearchConfig.parse_obj(constants.default_config["search-type"]),
+                search_type=SearchConfig.model_validate(constants.default_config["search-type"]),
                 processor=None,
             )
             state.config = default_full_config
@@ -116,7 +125,7 @@ async def update(
             configure_content,
             state.content_index,
             state.config.content_type,
-            indexer_input.dict(),
+            indexer_input.model_dump(),
             state.search_models,
             force,
             t,
diff --git a/src/khoj/routers/web_client.py b/src/khoj/routers/web_client.py
index bf3ff957..c17704bd 100644
--- a/src/khoj/routers/web_client.py
+++ b/src/khoj/routers/web_client.py
@@ -1,6 +1,8 @@
 # System Packages
 import json
 import os
+import math
+from datetime import timedelta
 
 # External Packages
 from fastapi import APIRouter
@@ -137,8 +139,9 @@ def config_page(request: Request):
     subscription_renewal_date = (
         user_subscription.renewal_date.strftime("%d %b %Y")
         if user_subscription and user_subscription.renewal_date
-        else None
+        else (user_subscription.created_at + timedelta(days=7)).strftime("%d %b %Y")
     )
+    indexed_data_size_in_mb = math.ceil(EntryAdapters.get_size_of_indexed_data_in_mb(user))
 
     enabled_content_source = set(EntryAdapters.get_unique_file_sources(user))
     successfully_configured = {
@@ -169,6 +172,7 @@ def config_page(request: Request):
             "khoj_cloud_subscription_url": os.getenv("KHOJ_CLOUD_SUBSCRIPTION_URL"),
             "is_active": has_required_scope(request, ["subscribed"]),
             "has_documents": has_documents,
+            "indexed_data_size_in_mb": indexed_data_size_in_mb,
         },
     )
 
diff --git a/tests/test_client.py b/tests/test_client.py
index 19aba03b..98affe27 100644
--- a/tests/test_client.py
+++ b/tests/test_client.py
@@ -125,6 +125,34 @@ def test_regenerate_with_invalid_content_type(client):
     assert response.status_code == 422
 
 
+# ----------------------------------------------------------------------------------------------------
+@pytest.mark.django_db(transaction=True)
+def test_index_update_big_files(client):
+    state.billing_enabled = True
+    # Arrange
+    files = get_big_size_sample_files_data()
+    headers = {"Authorization": "Bearer kk-secret"}
+
+    # Act
+    response = client.post("/api/v1/index/update", files=files, headers=headers)
+
+    # Assert
+    assert response.status_code == 429
+
+
+@pytest.mark.django_db(transaction=True)
+def test_index_update_big_files_no_billing(client):
+    # Arrange
+    files = get_big_size_sample_files_data()
+    headers = {"Authorization": "Bearer kk-secret"}
+
+    # Act
+    response = client.post("/api/v1/index/update", files=files, headers=headers)
+
+    # Assert
+    assert response.status_code == 200
+
+
 # ----------------------------------------------------------------------------------------------------
 @pytest.mark.django_db(transaction=True)
 def test_index_update(client):
@@ -421,3 +449,13 @@ def get_sample_files_data():
         ),
         ("files", ("path/to/filename2.md", "**Understanding science through the lens of art**", "text/markdown")),
     ]
+
+
+def get_big_size_sample_files_data():
+    big_text = "a" * (25 * 1024 * 1024)  # a string of approximately 25 MB
+    return [
+        (
+            "files",
+            ("path/to/filename.org", big_text, "text/org"),
+        )
+    ]