diff --git a/application/api/user/routes.py b/application/api/user/routes.py
index c33a6c84c..8e62683e6 100644
--- a/application/api/user/routes.py
+++ b/application/api/user/routes.py
@@ -433,6 +433,8 @@ class CombinedJson(Resource):
     @api.doc(description="Provide JSON file with combined available indexes")
     def get(self):
         user = "local"
+        sort_field = request.args.get('sort', 'date')  # Default to 'date'
+        sort_order = request.args.get('order', "desc")  # Default to 'desc'
         data = [
             {
                 "name": "default",
@@ -445,7 +447,7 @@ def get(self):
         ]
 
         try:
-            for index in sources_collection.find({"user": user}).sort("date", -1):
+            for index in sources_collection.find({"user": user}).sort(sort_field, 1 if sort_order=="asc" else -1):
                 data.append(
                     {
                         "id": str(index["_id"]),
diff --git a/frontend/src/Navigation.tsx b/frontend/src/Navigation.tsx
index ce23e90ef..3591469b1 100644
--- a/frontend/src/Navigation.tsx
+++ b/frontend/src/Navigation.tsx
@@ -254,7 +254,7 @@ export default function Navigation({ navOpen, setNavOpen }: NavigationProps) {
         ref={navRef}
         className={`${
           !navOpen && '-ml-96 md:-ml-[18rem]'
-        } duration-20 fixed top-0 z-40 flex h-full w-72 flex-col border-r-[1px] border-b-0 bg-white transition-all dark:border-r-purple-taupe dark:bg-chinese-black dark:text-white`}
+        } duration-20 fixed top-0 z-20 flex h-full w-72 flex-col border-r-[1px] border-b-0 bg-white transition-all dark:border-r-purple-taupe dark:bg-chinese-black dark:text-white`}
       >
         <div
           className={'visible mt-2 flex h-[6vh] w-full justify-between md:h-12'}
diff --git a/frontend/src/api/services/userService.ts b/frontend/src/api/services/userService.ts
index c5bbba7dd..53b38f50c 100644
--- a/frontend/src/api/services/userService.ts
+++ b/frontend/src/api/services/userService.ts
@@ -2,7 +2,8 @@ import apiClient from '../client';
 import endpoints from '../endpoints';
 
 const userService = {
-  getDocs: (): Promise<any> => apiClient.get(endpoints.USER.DOCS),
+  getDocs: (sort = 'date', order = 'desc'): Promise<any> =>
+    apiClient.get(`${endpoints.USER.DOCS}?sort=${sort}&order=${order}`),
   checkDocs: (data: any): Promise<any> =>
     apiClient.post(endpoints.USER.DOCS_CHECK, data),
   getAPIKeys: (): Promise<any> => apiClient.get(endpoints.USER.API_KEYS),
diff --git a/frontend/src/conversation/ConversationBubble.tsx b/frontend/src/conversation/ConversationBubble.tsx
index a9a05168b..284c2b568 100644
--- a/frontend/src/conversation/ConversationBubble.tsx
+++ b/frontend/src/conversation/ConversationBubble.tsx
@@ -474,7 +474,7 @@ function AllSources(sources: AllSourcesProps) {
                 ></img>
               ) : null}
             </span>
-            <p className="mt-3 max-h-24 overflow-y-auto break-words rounded-md text-left text-xs text-black dark:text-chinese-silver">
+            <p className="mt-3 max-h-16 overflow-y-auto break-words rounded-md text-left text-xs text-black dark:text-chinese-silver">
               {source.text}
             </p>
           </div>
diff --git a/frontend/src/preferences/preferenceApi.ts b/frontend/src/preferences/preferenceApi.ts
index ed730f7c6..af1060b83 100644
--- a/frontend/src/preferences/preferenceApi.ts
+++ b/frontend/src/preferences/preferenceApi.ts
@@ -3,9 +3,12 @@ import userService from '../api/services/userService';
 import { Doc } from '../models/misc';
 
 //Fetches all JSON objects from the source. We only use the objects with the "model" property in SelectDocsModal.tsx. Hopefully can clean up the source file later.
-export async function getDocs(): Promise<Doc[] | null> {
+export async function getDocs(
+  sort = 'date',
+  order = 'desc',
+): Promise<Doc[] | null> {
   try {
-    const response = await userService.getDocs();
+    const response = await userService.getDocs(sort, order);
     const data = await response.json();
 
     const docs: Doc[] = [];
diff --git a/frontend/src/settings/Documents.tsx b/frontend/src/settings/Documents.tsx
index 004b6f487..f94d1a87b 100644
--- a/frontend/src/settings/Documents.tsx
+++ b/frontend/src/settings/Documents.tsx
@@ -45,14 +45,30 @@ const Documents: React.FC<DocumentsProps> = ({
   const [modalState, setModalState] = useState<ActiveState>('INACTIVE'); // Initialize with inactive state
   const [isOnboarding, setIsOnboarding] = useState(false); // State for onboarding flag
   const [loading, setLoading] = useState(false);
-
+  const [sortField, setSortField] = useState<'date' | 'tokens'>('date');
+  const [sortOrder, setSortOrder] = useState<'asc' | 'desc'>('desc');
   const syncOptions = [
     { label: 'Never', value: 'never' },
     { label: 'Daily', value: 'daily' },
     { label: 'Weekly', value: 'weekly' },
     { label: 'Monthly', value: 'monthly' },
   ];
-
+  const refreshDocs = (field: 'date' | 'tokens') => {
+    if (field === sortField) {
+      setSortOrder(sortOrder === 'asc' ? 'desc' : 'asc');
+    } else {
+      setSortOrder('desc');
+      setSortField(field);
+    }
+    getDocs(sortField, sortOrder)
+      .then((data) => {
+        dispatch(setSourceDocs(data));
+      })
+      .catch((error) => console.error(error))
+      .finally(() => {
+        setLoading(false);
+      });
+  };
   const handleManageSync = (doc: Doc, sync_frequency: string) => {
     setLoading(true);
     userService
@@ -110,19 +126,28 @@ const Documents: React.FC<DocumentsProps> = ({
                   <th>
                     <div className="flex justify-center items-center">
                       {t('settings.documents.date')}
-                      <img src={caretSort} alt="" />
+                      <img
+                        className="cursor-pointer"
+                        onClick={() => refreshDocs('date')}
+                        src={caretSort}
+                        alt="sort"
+                      />
                     </div>
                   </th>
                   <th>
                     <div className="flex justify-center items-center">
                       {t('settings.documents.tokenUsage')}
-                      <img src={caretSort} alt="" />
+                      <img
+                        className="cursor-pointer"
+                        onClick={() => refreshDocs('tokens')}
+                        src={caretSort}
+                        alt="sort"
+                      />
                     </div>
                   </th>
                   <th>
                     <div className="flex justify-center items-center">
                       {t('settings.documents.type')}
-                      <img src={caretSort} alt="" />
                     </div>
                   </th>
                   <th></th>