diff --git a/apps/web/modules/feature-opt-in/hooks/useFeatureOptInBanner.ts b/apps/web/modules/feature-opt-in/hooks/useFeatureOptInBanner.ts
index 39a6b8d913..efbf962c18 100644
--- a/apps/web/modules/feature-opt-in/hooks/useFeatureOptInBanner.ts
+++ b/apps/web/modules/feature-opt-in/hooks/useFeatureOptInBanner.ts
@@ -3,7 +3,8 @@
 import type { OptInFeatureConfig } from "@calcom/features/feature-opt-in/config";
 import { getOptInFeatureConfig, shouldDisplayFeatureAt } from "@calcom/features/feature-opt-in/config";
 import { trpc } from "@calcom/trpc/react";
-import { useCallback, useEffect, useMemo, useState } from "react";
+import posthog from "posthog-js";
+import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import {
   getFeatureOptInTimestamp,
   isFeatureDismissed,
@@ -28,6 +29,12 @@ type FeatureOptInMutations = {
   invalidateQueries: () => void;
 };
 
+type FeatureOptInTrackingData = {
+  enableFor: "user" | "organization" | "teams";
+  teamCount?: number;
+  autoOptIn: boolean;
+};
+
 type UseFeatureOptInBannerResult = {
   shouldShow: boolean;
   isLoading: boolean;
@@ -41,6 +48,7 @@ type UseFeatureOptInBannerResult = {
   dismiss: () => void;
   markOptedIn: () => void;
   mutations: FeatureOptInMutations;
+  trackFeatureEnabled: (data: FeatureOptInTrackingData) => void;
 };
 
 function isFeatureOptedIn(featureId: string): boolean {
@@ -108,7 +116,12 @@ function useFeatureOptInBanner(featureId: string): UseFeatureOptInBannerResult {
     ]
   );
 
+  const hasBannerShownBeenTracked = useRef(false);
+
   const dismiss = useCallback(() => {
+    posthog.capture("feature_opt_in_banner_dismissed", {
+      feature_slug: featureId,
+    });
     setFeatureDismissed(featureId);
     setIsDismissed(true);
   }, [featureId]);
@@ -119,13 +132,28 @@ function useFeatureOptInBanner(featureId: string): UseFeatureOptInBannerResult {
   }, [featureId]);
 
   const openDialog = useCallback(() => {
+    posthog.capture("feature_opt_in_banner_try_it_clicked", {
+      feature_slug: featureId,
+    });
     setIsDialogOpen(true);
-  }, []);
+  }, [featureId]);
 
   const closeDialog = useCallback(() => {
     setIsDialogOpen(false);
   }, []);
 
+  const trackFeatureEnabled = useCallback(
+    (data: FeatureOptInTrackingData) => {
+      posthog.capture("feature_opt_in_enabled", {
+        feature_slug: featureId,
+        enable_for: data.enableFor,
+        team_count: data.teamCount,
+        auto_opt_in: data.autoOptIn,
+      });
+    },
+    [featureId]
+  );
+
   const shouldShow = useMemo(() => {
     if (isDismissed) return false;
     if (isOptedIn) return false;
@@ -137,6 +165,15 @@ function useFeatureOptInBanner(featureId: string): UseFeatureOptInBannerResult {
     return eligibilityQuery.data.status === "can_opt_in";
   }, [isDismissed, isOptedIn, featureConfig, eligibilityQuery.isLoading, eligibilityQuery.data]);
 
+  useEffect(() => {
+    if (shouldShow && !hasBannerShownBeenTracked.current) {
+      hasBannerShownBeenTracked.current = true;
+      posthog.capture("feature_opt_in_banner_shown", {
+        feature_slug: featureId,
+      });
+    }
+  }, [shouldShow, featureId]);
+
   return {
     shouldShow,
     isLoading: eligibilityQuery.isLoading,
@@ -150,6 +187,7 @@ function useFeatureOptInBanner(featureId: string): UseFeatureOptInBannerResult {
     dismiss,
     markOptedIn,
     mutations,
+    trackFeatureEnabled,
   };
 }
 
diff --git a/packages/features/feature-opt-in/components/FeatureOptInBannerWrapper.tsx b/packages/features/feature-opt-in/components/FeatureOptInBannerWrapper.tsx
index 91b5aa55d2..63d501cd48 100644
--- a/packages/features/feature-opt-in/components/FeatureOptInBannerWrapper.tsx
+++ b/packages/features/feature-opt-in/components/FeatureOptInBannerWrapper.tsx
@@ -15,6 +15,12 @@ type UserRoleContext = {
   adminTeamNames: { id: number; name: string }[];
 };
 
+type FeatureOptInTrackingData = {
+  enableFor: "user" | "organization" | "teams";
+  teamCount?: number;
+  autoOptIn: boolean;
+};
+
 type FeatureOptInBannerState = {
   shouldShow: boolean;
   isLoading: boolean;
@@ -28,6 +34,7 @@ type FeatureOptInBannerState = {
   dismiss: () => void;
   markOptedIn: () => void;
   mutations: FeatureOptInMutations;
+  trackFeatureEnabled: (data: FeatureOptInTrackingData) => void;
 };
 
 interface FeatureOptInBannerWrapperProps {
@@ -60,6 +67,7 @@ function FeatureOptInBannerWrapper({ state }: FeatureOptInBannerWrapperProps): R
           featureConfig={state.featureConfig}
           userRoleContext={state.userRoleContext}
           mutations={state.mutations}
+          onTrackFeatureEnabled={state.trackFeatureEnabled}
         />
       )}
     </>
diff --git a/packages/features/feature-opt-in/components/FeatureOptInConfirmDialog.tsx b/packages/features/feature-opt-in/components/FeatureOptInConfirmDialog.tsx
index 2aa245e358..8ac01916ff 100644
--- a/packages/features/feature-opt-in/components/FeatureOptInConfirmDialog.tsx
+++ b/packages/features/feature-opt-in/components/FeatureOptInConfirmDialog.tsx
@@ -41,6 +41,12 @@ export type FeatureOptInMutations = {
   invalidateQueries: () => void;
 };
 
+type FeatureOptInTrackingData = {
+  enableFor: "user" | "organization" | "teams";
+  teamCount?: number;
+  autoOptIn: boolean;
+};
+
 interface FeatureOptInConfirmDialogProps {
   isOpen: boolean;
   onClose: () => void;
@@ -49,6 +55,7 @@ interface FeatureOptInConfirmDialogProps {
   featureConfig: OptInFeatureConfig;
   userRoleContext: UserRoleContext;
   mutations: FeatureOptInMutations;
+  onTrackFeatureEnabled?: (data: FeatureOptInTrackingData) => void;
 }
 
 export function FeatureOptInConfirmDialog({
@@ -59,6 +66,7 @@ export function FeatureOptInConfirmDialog({
   featureConfig,
   userRoleContext,
   mutations,
+  onTrackFeatureEnabled,
 }: FeatureOptInConfirmDialogProps): ReactElement {
   const { t } = useLocale();
   const router = useRouter();
@@ -159,6 +167,13 @@ export function FeatureOptInConfirmDialog({
 
       await Promise.all(promises);
 
+      const enableFor = enableForOrg ? "organization" : hasTeamsSelected ? "teams" : "user";
+      onTrackFeatureEnabled?.({
+        enableFor,
+        teamCount: hasTeamsSelected ? selectedTeamIds.length : undefined,
+        autoOptIn,
+      });
+
       setIsSuccess(true);
       setShouldInvalidate(true);
       onOptInSuccess?.();