diff --git a/src/components/AIChat/AIChat.tsx b/src/components/AIChat/AIChat.tsx
index 0689b66bf..652206d56 100644
--- a/src/components/AIChat/AIChat.tsx
+++ b/src/components/AIChat/AIChat.tsx
@@ -32,7 +32,6 @@ import {
 import { RoadmapRecommendations } from '../RoadmapAIChat/RoadmapRecommendations';
 import { AIChatCourse } from './AIChatCouse';
 import { showLoginPopup } from '../../lib/popup';
-import { UpgradeAccountModal } from '../Billing/UpgradeAccountModal';
 import { readChatStream } from '../../lib/chat';
 import { chatHistoryOptions } from '../../queries/chat-history';
 import { cn } from '../../lib/classname';
@@ -51,6 +50,7 @@ type AIChatProps = {
   messages?: RoadmapAIChatHistoryType[];
   chatHistoryId?: string;
   setChatHistoryId?: (chatHistoryId: string) => void;
+  onUpgrade?: () => void;
 };
 
 export function AIChat(props: AIChatProps) {
@@ -58,6 +58,7 @@ export function AIChat(props: AIChatProps) {
     messages: defaultMessages,
     chatHistoryId: defaultChatHistoryId,
     setChatHistoryId: setDefaultChatHistoryId,
+    onUpgrade,
   } = props;
 
   const toast = useToast();
@@ -70,7 +71,6 @@ export function AIChat(props: AIChatProps) {
     RoadmapAIChatHistoryType[]
   >(defaultMessages ?? []);
 
-  const [showUpgradeModal, setShowUpgradeModal] = useState(false);
   const [isPersonalizedResponseFormOpen, setIsPersonalizedResponseFormOpen] =
     useState(false);
   const [isUploadResumeModalOpen, setIsUploadResumeModalOpen] = useState(false);
@@ -128,7 +128,7 @@ export function AIChat(props: AIChatProps) {
 
     if (isLimitExceeded) {
       if (!isPaidUser) {
-        setShowUpgradeModal(true);
+        onUpgrade?.();
       }
 
       toast.error('Limit reached for today. Please wait until tomorrow.');
@@ -342,7 +342,7 @@ export function AIChat(props: AIChatProps) {
     (index: number) => {
       if (isLimitExceeded) {
         if (!isPaidUser) {
-          setShowUpgradeModal(true);
+          onUpgrade?.();
         }
 
         toast.error('Limit reached for today. Please wait until tomorrow.');
@@ -429,10 +429,6 @@ export function AIChat(props: AIChatProps) {
         />
       )}
 
-      {showUpgradeModal && (
-        <UpgradeAccountModal onClose={() => setShowUpgradeModal(false)} />
-      )}
-
       <div
         className="pointer-events-none absolute right-0 bottom-0 left-0 mx-auto w-full max-w-3xl px-4"
         ref={chatContainerRef}
@@ -446,7 +442,7 @@ export function AIChat(props: AIChatProps) {
               </div>
               <button
                 type="button"
-                onClick={() => setShowUpgradeModal(true)}
+                onClick={() => onUpgrade?.()}
                 className="shrink-0 cursor-pointer rounded-md bg-yellow-200 px-2 py-1 text-xs font-medium text-yellow-800 hover:bg-yellow-200"
               >
                 Upgrade to Pro
@@ -540,7 +536,7 @@ export function AIChat(props: AIChatProps) {
                 <button
                   type="button"
                   onClick={() => {
-                    setShowUpgradeModal(true);
+                    onUpgrade?.();
                   }}
                   className="rounded-md bg-white px-2 py-1 text-xs font-medium text-black hover:bg-gray-300"
                 >
diff --git a/src/components/AIChatHistory/AIChatHistory.tsx b/src/components/AIChatHistory/AIChatHistory.tsx
index dde0d8d3f..e27845305 100644
--- a/src/components/AIChatHistory/AIChatHistory.tsx
+++ b/src/components/AIChatHistory/AIChatHistory.tsx
@@ -9,6 +9,7 @@ import { ListChatHistory } from './ListChatHistory';
 import { billingDetailsOptions } from '../../queries/billing';
 import { ChatHistoryError } from './ChatHistoryError';
 import { useClientMount } from '../../hooks/use-client-mount';
+import { UpgradeAccountModal } from '../Billing/UpgradeAccountModal';
 
 type AIChatHistoryProps = {
   chatHistoryId?: string;
@@ -19,6 +20,7 @@ export function AIChatHistory(props: AIChatHistoryProps) {
 
   const isClientMounted = useClientMount();
   const [keyTrigger, setKeyTrigger] = useState(0);
+  const [showUpgradeModal, setShowUpgradeModal] = useState(false);
   const [isChatHistoryLoading, setIsChatHistoryLoading] = useState(true);
   const [chatHistoryId, setChatHistoryId] = useState<string | undefined>(
     defaultChatHistoryId || undefined,
@@ -116,13 +118,15 @@ export function AIChatHistory(props: AIChatHistoryProps) {
   return (
     <AIChatLayout>
       <div className="relative flex grow">
-        {isPaidUser && (
-          <ListChatHistory
-            activeChatHistoryId={chatHistoryId}
-            onChatHistoryClick={handleChatHistoryClick}
-            onDelete={handleDelete}
-          />
-        )}
+        <ListChatHistory
+          activeChatHistoryId={chatHistoryId}
+          onChatHistoryClick={handleChatHistoryClick}
+          onDelete={handleDelete}
+          isPaidUser={isPaidUser}
+          onUpgrade={() => {
+            setShowUpgradeModal(true);
+          }}
+        />
 
         <div className="relative flex grow">
           {showLoader && (
@@ -151,10 +155,17 @@ export function AIChatHistory(props: AIChatHistoryProps) {
                   },
                 });
               }}
+              onUpgrade={() => {
+                setShowUpgradeModal(true);
+              }}
             />
           )}
         </div>
       </div>
+
+      {showUpgradeModal && (
+        <UpgradeAccountModal onClose={() => setShowUpgradeModal(false)} />
+      )}
     </AIChatLayout>
   );
 }
diff --git a/src/components/AIChatHistory/ListChatHistory.tsx b/src/components/AIChatHistory/ListChatHistory.tsx
index b7bf09fbc..fc906b370 100644
--- a/src/components/AIChatHistory/ListChatHistory.tsx
+++ b/src/components/AIChatHistory/ListChatHistory.tsx
@@ -4,6 +4,7 @@ import { queryClient } from '../../stores/query-client';
 import { ChatHistoryItem } from './ChatHistoryItem';
 import {
   Loader2Icon,
+  LockIcon,
   PanelLeftCloseIcon,
   PanelLeftIcon,
   PlusIcon,
@@ -24,10 +25,18 @@ type ListChatHistoryProps = {
   activeChatHistoryId?: string;
   onChatHistoryClick: (chatHistoryId: string | null) => void;
   onDelete?: (chatHistoryId: string) => void;
+  isPaidUser?: boolean;
+  onUpgrade?: () => void;
 };
 
 export function ListChatHistory(props: ListChatHistoryProps) {
-  const { activeChatHistoryId, onChatHistoryClick, onDelete } = props;
+  const {
+    activeChatHistoryId,
+    onChatHistoryClick,
+    onDelete,
+    isPaidUser,
+    onUpgrade,
+  } = props;
 
   const [isOpen, setIsOpen] = useState(true);
   const [isLoading, setIsLoading] = useState(true);
@@ -85,14 +94,49 @@ export function ListChatHistory(props: ListChatHistoryProps) {
     (group) => group.histories.length === 0,
   );
 
-  return (
-    <div
-      className={cn(
-        'flex w-[255px] shrink-0 flex-col justify-start border-r border-gray-200 bg-white p-2',
-        'max-md:absolute max-md:inset-0 max-md:z-20 max-md:w-full',
-        !isOpen && 'hidden',
-      )}
+  const classNames = cn(
+    'flex w-[255px] shrink-0 flex-col justify-start border-r border-gray-200 bg-white p-2',
+    'max-md:absolute max-md:inset-0 max-md:z-20 max-md:w-full',
+    !isOpen && 'hidden',
+  );
+
+  const closeButton = (
+    <button
+      className="flex size-8 items-center justify-center rounded-lg p-1 text-gray-500 hover:bg-gray-100 hover:text-black"
+      onClick={() => {
+        setIsOpen(false);
+      }}
     >
+      <PanelLeftCloseIcon className="h-4.5 w-4.5" />
+    </button>
+  );
+
+  if (!isPaidUser) {
+    return (
+      <div className={cn(classNames, 'relative')}>
+        <div className="absolute top-2 right-2">{closeButton}</div>
+
+        <div className="flex grow flex-col items-center justify-center">
+          <LockIcon className="size-8 text-gray-500" />
+          <p className="mt-4 text-center text-sm text-balance text-gray-500">
+            Upgrade to Pro to keep your chat history.
+          </p>
+          <button
+            type="button"
+            className="mt-2 shrink-0 cursor-pointer rounded-md bg-yellow-200 px-2.5 py-1.5 text-sm font-medium text-yellow-800 hover:bg-yellow-200"
+            onClick={() => {
+              onUpgrade?.();
+            }}
+          >
+            Upgrade to Pro
+          </button>
+        </div>
+      </div>
+    );
+  }
+
+  return (
+    <div className={classNames}>
       {isLoading && <ListChatHistorySkeleton />}
       {!isLoading && isError && <ChatHistoryError error={error} />}
 
@@ -101,18 +145,11 @@ export function ListChatHistory(props: ListChatHistoryProps) {
           <div>
             <div className="mb-4 flex items-center justify-between">
               <h1 className="font-medium text-gray-900">Chat History</h1>
-              <button
-                className="flex size-8 items-center justify-center rounded-lg p-1 hover:bg-gray-100"
-                onClick={() => {
-                  setIsOpen(false);
-                }}
-              >
-                <PanelLeftCloseIcon className="h-4.5 w-4.5" />
-              </button>
+              {closeButton}
             </div>
 
             <button
-              className="flex w-full items-center hover:opacity-80 justify-center gap-2 rounded-lg bg-black p-2 text-sm text-white"
+              className="flex w-full items-center justify-center gap-2 rounded-lg bg-black p-2 text-sm text-white hover:opacity-80"
               onClick={() => {
                 if (isMobile) {
                   setIsOpen(false);