diff --git a/src/components/AITutor/AITutorSidebar.tsx b/src/components/AITutor/AITutorSidebar.tsx
index 0bb5b801a..5be788fe8 100644
--- a/src/components/AITutor/AITutorSidebar.tsx
+++ b/src/components/AITutor/AITutorSidebar.tsx
@@ -1,6 +1,7 @@
 import {
   BookOpen,
   Compass,
+  Map,
   MessageCircle,
   Plus,
   Star,
@@ -39,6 +40,12 @@ const sidebarItems = [
     href: '/ai/chat',
     icon: MessageCircle,
   },
+  {
+    key: 'roadmap-chat',
+    label: 'Roadmap Chat',
+    href: '/ai/roadmap-chat',
+    icon: Map,
+  },
   {
     key: 'library',
     label: 'My Learning',
diff --git a/src/components/RoadmapAIChat/RoadmapChatListing.tsx b/src/components/RoadmapAIChat/RoadmapChatListing.tsx
new file mode 100644
index 000000000..9f39051ad
--- /dev/null
+++ b/src/components/RoadmapAIChat/RoadmapChatListing.tsx
@@ -0,0 +1,117 @@
+import { useState, useMemo, useEffect, useRef } from 'react';
+import { cn } from '../../lib/classname';
+
+export type RoadmapChatListingItem = {
+  id: string;
+  title: string;
+  description?: string;
+  category?: 'role' | 'skill' | string; // default to string for flexibility
+};
+
+type RoadmapChatListingProps = {
+  roadmaps: RoadmapChatListingItem[];
+  className?: string;
+};
+
+export default function RoadmapChatListing(props: RoadmapChatListingProps) {
+  const { roadmaps, className } = props;
+
+  const [search, setSearch] = useState('');
+  const searchInputRef = useRef<HTMLInputElement>(null);
+
+  // Auto-focus the search input
+  useEffect(() => {
+    if (searchInputRef.current) {
+      searchInputRef.current.focus();
+    }
+  }, []);
+
+  const filteredRoadmaps = useMemo(() => {
+    const term = search.trim().toLowerCase();
+    if (!term) {
+      return roadmaps;
+    }
+
+    return roadmaps.filter((roadmap) => {
+      return (
+        roadmap.title.toLowerCase().includes(term) ||
+        roadmap.id.toLowerCase().includes(term)
+      );
+    });
+  }, [search, roadmaps]);
+
+  // Separate into role-based and skill-based
+  const roleRoadmaps = filteredRoadmaps.filter((rm) => rm.category === 'role');
+  const skillRoadmaps = filteredRoadmaps.filter(
+    (rm) => rm.category === 'skill',
+  );
+
+  return (
+    <div className={cn('flex w-full flex-col', className)}>
+      <input
+        ref={searchInputRef}
+        type="text"
+        placeholder="Search roadmaps..."
+        value={search}
+        onChange={(e) => setSearch(e.target.value)}
+        className="mb-6 w-full rounded-lg border border-gray-300 bg-white px-4 py-2.5 text-sm placeholder-gray-400 focus:border-gray-300 focus:outline-none"
+      />
+
+      <div className="flex flex-col gap-8">
+        {/* Role-based roadmaps */}
+        {roleRoadmaps.length > 0 && (
+          <div>
+            <h2 className="mb-4 text-xs tracking-wide text-gray-400 uppercase">
+              Role-based Roadmaps
+            </h2>
+            <div className="grid grid-cols-1 gap-1.5 sm:grid-cols-2 md:grid-cols-3">
+              {roleRoadmaps.map((roadmap) => (
+                <a
+                  key={roadmap.id}
+                  href={`/${roadmap.id}/ai`}
+                  className="relative truncate rounded-md border bg-white p-2.5 text-left text-sm shadow-xs hover:border-gray-400 hover:bg-gray-50"
+                >
+                  {roadmap.title}
+                </a>
+              ))}
+              {roleRoadmaps.length === 0 && (
+                <div className="col-span-full py-4 text-center">
+                  <p className="text-sm text-gray-400">
+                    No role-based roadmaps found.
+                  </p>
+                </div>
+              )}
+            </div>
+          </div>
+        )}
+
+        {/* Skill-based roadmaps */}
+        {skillRoadmaps.length > 0 && (
+          <div>
+            <h2 className="mb-4 text-xs tracking-wide text-gray-400 uppercase">
+              Skill-based Roadmaps
+            </h2>
+            <div className="grid grid-cols-1 gap-1.5 sm:grid-cols-2 md:grid-cols-3">
+              {skillRoadmaps.map((roadmap) => (
+                <a
+                  key={roadmap.id}
+                  href={`/${roadmap.id}/ai`}
+                  className="relative truncate rounded-md border bg-white p-2.5 text-left text-sm shadow-xs hover:border-gray-400 hover:bg-gray-50"
+                >
+                  {roadmap.title}
+                </a>
+              ))}
+              {skillRoadmaps.length === 0 && (
+                <div className="col-span-full py-4 text-center">
+                  <p className="text-sm text-gray-400">
+                    No skill-based roadmaps found.
+                  </p>
+                </div>
+              )}
+            </div>
+          </div>
+        )}
+      </div>
+    </div>
+  );
+}
diff --git a/src/pages/ai/roadmap-chat.astro b/src/pages/ai/roadmap-chat.astro
new file mode 100644
index 000000000..d5bca4ed3
--- /dev/null
+++ b/src/pages/ai/roadmap-chat.astro
@@ -0,0 +1,54 @@
+---
+import SkeletonLayout from '../../layouts/SkeletonLayout.astro';
+import { AITutorLayout } from '../../components/AITutor/AITutorLayout';
+import RoadmapChatListing from '../../components/RoadmapAIChat/RoadmapChatListing';
+import {
+  getRoadmapIds,
+  getRoadmapById,
+  resourceTitleFromId,
+} from '../../lib/roadmap';
+
+const ids = await getRoadmapIds();
+const roadmapsRaw = await Promise.all(ids.map((id) => getRoadmapById(id)));
+
+const roadmaps = roadmapsRaw.map((rm) => {
+  const tags = rm.frontmatter.tags || [];
+  const category = tags.includes('role-roadmap')
+    ? 'role'
+    : tags.includes('skill-roadmap')
+      ? 'skill'
+      : 'other';
+
+  return {
+    id: rm.id,
+    title: rm.frontmatter.title || resourceTitleFromId(rm.id),
+    description:
+      rm.frontmatter.briefDescription || rm.frontmatter.description || '',
+    category,
+  };
+});
+
+const ogImage = 'https://roadmap.sh/og-images/ai-tutor.png';
+---
+
+<SkeletonLayout
+  title='Roadmap AI Chat'
+  noIndex={true}
+  ogImageUrl={ogImage}
+  description='Chat with AI Tutor on any roadmap. Pick a roadmap to start chatting.'
+>
+  <AITutorLayout activeTab='roadmap-chat' client:load>
+    <div class='mx-auto flex w-full max-w-3xl flex-grow flex-col p-4'>
+      <div class='mb-6 text-left'>
+        <h1 class='mb-2 text-4xl font-semibold max-md:text-xl'>
+          Chat with a Roadmap
+        </h1>
+        <p class='text-base text-gray-600 max-md:text-sm'>
+          Select a roadmap and start learning with AI as a guide.
+        </p>
+      </div>
+      <RoadmapChatListing client:load roadmaps={roadmaps} />
+    </div>
+  </AITutorLayout>
+</SkeletonLayout>
+