diff --git a/apps/docs/components/GuidesSidebar.tsx b/apps/docs/components/GuidesSidebar.tsx
index 24e68d7cc83..7945943892a 100644
--- a/apps/docs/components/GuidesSidebar.tsx
+++ b/apps/docs/components/GuidesSidebar.tsx
@@ -11,6 +11,7 @@ import { Feedback } from '~/components/Feedback'
 import { useTocAnchors } from '../features/docs/GuidesMdx.state'
 import { Chatgpt } from 'icons'
 import { Claude } from 'icons'
+import { useSendTelemetryEvent } from '~/lib/telemetry'
 
 interface TOCHeader {
   id?: string
@@ -22,6 +23,7 @@ interface TOCHeader {
 function AiTools({ className }: { className?: string }) {
   const [copied, setCopied] = useState(false)
   const path = usePathname()
+  const sendTelemetryEvent = useSendTelemetryEvent()
 
   async function copyMarkdown() {
     const mdUrl = `/docs/${path}.md`
@@ -35,6 +37,10 @@ function AiTools({ className }: { className?: string }) {
     } catch (error) {
       console.error('Failed to copy markdown', error)
     }
+
+    sendTelemetryEvent({
+      action: 'copy_as_markdown_clicked',
+    })
   }
 
   return (
@@ -60,6 +66,9 @@ function AiTools({ className }: { className?: string }) {
         <a
           href={`https://chatgpt.com/?hint=search&q=Read from https://supabase.com/docs${path} so I can ask questions about its contents`}
           target="_blank"
+          onClick={() =>
+            sendTelemetryEvent({ action: 'ask_ai_clicked', properties: { agent: 'chatgpt' } })
+          }
           rel="noreferrer noopener"
           className="flex items-center gap-1.5 text-xs text-foreground-lighter hover:text-foreground transition-colors"
         >
@@ -69,6 +78,9 @@ function AiTools({ className }: { className?: string }) {
         <a
           href={`https://claude.ai/new?q=Read from https://supabase.com/docs${path} so I can ask questions about its contents`}
           target="_blank"
+          onClick={() =>
+            sendTelemetryEvent({ action: 'ask_ai_clicked', properties: { agent: 'claude' } })
+          }
           rel="noreferrer noopener"
           className="flex items-center gap-1.5 text-xs text-foreground-lighter hover:text-foreground transition-colors"
         >
diff --git a/packages/common/telemetry-constants.ts b/packages/common/telemetry-constants.ts
index 9ff732856ea..f6f0f40c1e6 100644
--- a/packages/common/telemetry-constants.ts
+++ b/packages/common/telemetry-constants.ts
@@ -747,6 +747,29 @@ export interface DocsFeedbackClickedEvent {
   }
 }
 
+/**
+ * User clicked 'Copy as Markdown' option on a page.
+ *
+ * @group Events
+ * @source docs
+ */
+export interface CopyAsMarkdownEvent {
+  action: 'copy_as_markdown_clicked'
+}
+
+/**
+ * User clicked "Ask..." to open a new window to consult an agent about the current page.
+ *
+ * @group Events
+ * @source docs
+ */
+export interface AskAIEvent {
+  action: 'ask_ai_clicked'
+  properties: {
+    agent: 'chatgpt' | 'claude'
+  }
+}
+
 /**
  * User clicked the framework quickstart card on the homepage, leading to the specific framework documentation.
  *
@@ -2974,6 +2997,8 @@ export type TelemetryEvent =
   | AssistantEditInSqlEditorClickedEvent
   | AssistantMessageRatingSubmittedEvent
   | DocsFeedbackClickedEvent
+  | CopyAsMarkdownEvent
+  | AskAIEvent
   | HomepageFrameworkQuickstartClickedEvent
   | HomepageProductCardClickedEvent
   | WwwPricingPlanCtaClickedEvent