diff --git a/src/components/AITutor/AITutorSidebar.tsx b/src/components/AITutor/AITutorSidebar.tsx
index 5ee4fccc2..471d75849 100644
--- a/src/components/AITutor/AITutorSidebar.tsx
+++ b/src/components/AITutor/AITutorSidebar.tsx
@@ -1,5 +1,9 @@
-import { BookOpen, Compass, Plus, Star, X } from 'lucide-react';
+import { useEffect, useState } from 'react';
+import { BookOpen, Compass, Plus, Star, X, Zap } from 'lucide-react';
 import { AITutorLogo } from '../ReactIcons/AITutorLogo';
+import { UpgradeAccountModal } from '../Billing/UpgradeAccountModal';
+import { useIsPaidUser } from '../../queries/billing';
+import { isLoggedIn } from '../../lib/jwt';
 
 type AITutorSidebarProps = {
   isFloating: boolean;
@@ -39,8 +43,21 @@ export type AITutorTab = (typeof sidebarItems)[number]['key'];
 export function AITutorSidebar(props: AITutorSidebarProps) {
   const { activeTab, isFloating, onClose } = props;
 
+  const [isInitialLoad, setIsInitialLoad] = useState(true);
+
+  const [isUpgradeModalOpen, setIsUpgradeModalOpen] = useState(false);
+  const { isPaidUser, isLoading: isPaidUserLoading } = useIsPaidUser();
+
+  useEffect(() => {
+    setIsInitialLoad(false);
+  }, []);
+
   return (
     <>
+      {isUpgradeModalOpen && (
+        <UpgradeAccountModal onClose={() => setIsUpgradeModalOpen(false)} />
+      )}
+
       <aside
         className={`w-[255px] shrink-0 border-r border-slate-200 ${
           isFloating
@@ -94,6 +111,28 @@ export function AITutorSidebar(props: AITutorSidebarProps) {
               </a>
             </li>
           ))}
+
+          {!isInitialLoad &&
+            isLoggedIn() &&
+            !isPaidUser &&
+            !isPaidUserLoading && (
+              <li>
+                <button
+                  onClick={() => {
+                    setIsUpgradeModalOpen(true);
+                  }}
+                  className="mx-4 mt-4 rounded-xl bg-amber-100 p-4 text-left transition-colors hover:bg-amber-200/80"
+                >
+                  <span className="mb-2 flex items-center gap-2">
+                    <Zap className="size-4 text-amber-600" />
+                    <span className="font-medium text-amber-900">Upgrade</span>
+                  </span>
+                  <span className="mt-1 block text-left text-xs leading-4 text-amber-700">
+                    Get access to all features and benefits of the AI Tutor.
+                  </span>
+                </button>
+              </li>
+            )}
         </ul>
       </aside>
       {isFloating && (
diff --git a/src/components/AITutor/AITutorSidebarProps.tsx b/src/components/AITutor/AITutorSidebarProps.tsx
new file mode 100644
index 000000000..8ede3e1a4
--- /dev/null
+++ b/src/components/AITutor/AITutorSidebarProps.tsx
@@ -0,0 +1,13 @@
+import { Zap } from 'lucide-react';
+
+<li>
+  <div className="mx-4 mt-4 rounded-lg bg-amber-50 p-3">
+    <div className="flex items-center gap-2">
+      <Zap className="size-4 text-amber-600" />
+      <span className="font-medium text-amber-900">Free Tier</span>
+    </div>
+    <p className="mt-1 text-xs text-amber-700">
+      Upgrade to Pro to unlock unlimited AI tutoring sessions
+    </p>
+  </div>
+</li> 
\ No newline at end of file
diff --git a/src/components/Billing/UpgradeAccountModal.tsx b/src/components/Billing/UpgradeAccountModal.tsx
index 452fd2665..359c4acab 100644
--- a/src/components/Billing/UpgradeAccountModal.tsx
+++ b/src/components/Billing/UpgradeAccountModal.tsx
@@ -234,7 +234,14 @@ export function UpgradeAccountModal(props: UpgradeAccountModalProps) {
                           )}
                         </p>
                       )}
-                      <p className="text-2xl font-bold text-black sm:text-3xl">
+                      <p
+                        className={cn(
+                          'text-2xl font-bold text-black sm:text-3xl',
+                          {
+                            'mt-0 md:mt-6': !isYearly,
+                          },
+                        )}
+                      >
                         ${plan.amount}{' '}
                         <span className="text-xs font-normal text-gray-500 sm:text-sm">
                           / {isYearly ? 'year' : 'month'}