diff --git a/src/components/AIRoadmap/AIRoadmapRegenerate.tsx b/src/components/AIRoadmap/AIRoadmapRegenerate.tsx
new file mode 100644
index 000000000..ac5d198ff
--- /dev/null
+++ b/src/components/AIRoadmap/AIRoadmapRegenerate.tsx
@@ -0,0 +1,158 @@
+import { PenSquare, RefreshCcw, SettingsIcon } from 'lucide-react';
+import { useRef, useState } from 'react';
+import { useOutsideClick } from '../../hooks/use-outside-click';
+import { cn } from '../../lib/classname';
+import { UpgradeAccountModal } from '../Billing/UpgradeAccountModal';
+import { ModifyCoursePrompt } from '../GenerateCourse/ModifyCoursePrompt';
+import type { QuestionAnswerChatMessage } from '../ContentGenerator/QuestionAnswerChat';
+import { useMutation, useQuery } from '@tanstack/react-query';
+import { queryClient } from '../../stores/query-client';
+import { httpPost } from '../../lib/query-http';
+import { aiRoadmapOptions } from '../../queries/ai-roadmap';
+import { UpdatePreferences } from '../GenerateGuide/UpdatePreferences';
+
+type AIRoadmapRegenerateProps = {
+  onRegenerate: (prompt?: string) => void;
+  roadmapSlug: string;
+};
+
+export function AIRoadmapRegenerate(props: AIRoadmapRegenerateProps) {
+  const { onRegenerate, roadmapSlug } = props;
+
+  const [isDropdownVisible, setIsDropdownVisible] = useState(false);
+  const [showUpgradeModal, setShowUpgradeModal] = useState(false);
+  const [showPromptModal, setShowPromptModal] = useState(false);
+  const [showUpdatePreferencesModal, setShowUpdatePreferencesModal] =
+    useState(false);
+
+  const ref = useRef<HTMLDivElement>(null);
+
+  useOutsideClick(ref, () => setIsDropdownVisible(false));
+
+  const { data: aiRoadmap } = useQuery(
+    aiRoadmapOptions(roadmapSlug),
+    queryClient,
+  );
+  const { mutate: updatePreferences, isPending: isUpdating } = useMutation(
+    {
+      mutationFn: (questionAndAnswers: QuestionAnswerChatMessage[]) => {
+        return httpPost(`/v1-update-ai-roadmap-preferences/${roadmapSlug}`, {
+          questionAndAnswers,
+        });
+      },
+      onSuccess: (_, vars) => {
+        queryClient.setQueryData(
+          aiRoadmapOptions(roadmapSlug).queryKey,
+          (old) => {
+            if (!old) {
+              return old;
+            }
+
+            return {
+              ...old,
+              questionAndAnswers: vars,
+            };
+          },
+        );
+
+        setShowUpdatePreferencesModal(false);
+        setIsDropdownVisible(false);
+        onRegenerate();
+      },
+    },
+    queryClient,
+  );
+
+  return (
+    <>
+      {showUpgradeModal && (
+        <UpgradeAccountModal
+          onClose={() => {
+            setShowUpgradeModal(false);
+          }}
+        />
+      )}
+
+      {showPromptModal && (
+        <ModifyCoursePrompt
+          description="Pass additional information to the AI to generate a roadmap."
+          onClose={() => setShowPromptModal(false)}
+          onSubmit={(prompt) => {
+            setShowPromptModal(false);
+            onRegenerate(prompt);
+          }}
+        />
+      )}
+
+      {showUpdatePreferencesModal && (
+        <UpdatePreferences
+          onClose={() => setShowUpdatePreferencesModal(false)}
+          questionAndAnswers={aiRoadmap?.questionAndAnswers}
+          term={aiRoadmap?.term || ''}
+          format="roadmap"
+          onUpdatePreferences={(questionAndAnswers) => {
+            updatePreferences(questionAndAnswers);
+          }}
+          isUpdating={isUpdating}
+        />
+      )}
+
+      <div ref={ref} className="relative flex items-stretch">
+        <button
+          className={cn('rounded-md px-2.5 text-gray-400 hover:text-black', {
+            'text-black': isDropdownVisible,
+          })}
+          onClick={() => setIsDropdownVisible(!isDropdownVisible)}
+        >
+          <PenSquare className="text-current" size={16} strokeWidth={2.5} />
+        </button>
+        {isDropdownVisible && (
+          <div className="absolute top-full right-0 min-w-[190px] translate-y-1 overflow-hidden rounded-md border border-gray-200 bg-white shadow-md">
+            <button
+              onClick={() => {
+                setIsDropdownVisible(false);
+                setShowUpdatePreferencesModal(true);
+              }}
+              className="flex w-full items-center gap-2.5 px-3 py-2 text-left text-sm text-gray-600 hover:bg-gray-100"
+            >
+              <SettingsIcon
+                size={16}
+                className="text-gray-400"
+                strokeWidth={2.5}
+              />
+              Update Preferences
+            </button>
+            <button
+              onClick={() => {
+                setIsDropdownVisible(false);
+                onRegenerate();
+              }}
+              className="flex w-full items-center gap-2.5 px-3 py-2 text-left text-sm text-gray-600 hover:bg-gray-100"
+            >
+              <RefreshCcw
+                size={16}
+                className="text-gray-400"
+                strokeWidth={2.5}
+              />
+              Regenerate
+            </button>
+            <button
+              onClick={() => {
+                setIsDropdownVisible(false);
+                setShowPromptModal(true);
+              }}
+              className="flex w-full items-center gap-2.5 px-3 py-2 text-left text-sm text-gray-600 hover:bg-gray-100"
+            >
+              <PenSquare
+                size={16}
+                className="text-gray-400"
+                strokeWidth={2.5}
+              />
+              Modify Prompt
+            </button>
+          </div>
+        )}
+      </div>
+    </>
+  );
+}
diff --git a/src/components/GenerateGuide/UpdatePreferences.tsx b/src/components/GenerateGuide/UpdatePreferences.tsx
index 8869edcd7..c3f485a46 100644
--- a/src/components/GenerateGuide/UpdatePreferences.tsx
+++ b/src/components/GenerateGuide/UpdatePreferences.tsx
@@ -55,7 +55,7 @@ export function UpdatePreferences(props: UpdatePreferencesProps) {
       <div className="flex flex-col gap-1">
         <h2 className="text-lg font-medium">Update Preferences</h2>
         <p className="text-sm text-gray-500">
-          Update the preferences for the AI to generate a guide.
+          Update the preferences for the AI to generate a {format}.
         </p>
       </div>
 
diff --git a/src/queries/ai-roadmap.ts b/src/queries/ai-roadmap.ts
index 7ecac3f6b..ce4f7725c 100644
--- a/src/queries/ai-roadmap.ts
+++ b/src/queries/ai-roadmap.ts
@@ -14,6 +14,9 @@ export interface AIRoadmapDocument {
   viewCount: number;
   lastVisitedAt: Date;
   keyType?: 'system' | 'user';
+
+  questionAndAnswers?: QuestionAnswerChatMessage[];
+
   createdAt: Date;
   updatedAt: Date;
 }