diff --git a/.cursor/settings.json b/.cursor/settings.json
new file mode 100644
index 000000000..b459ee22e
--- /dev/null
+++ b/.cursor/settings.json
@@ -0,0 +1,7 @@
+{
+  "plugins": {
+    "posthog": {
+      "enabled": true
+    }
+  }
+}
diff --git a/apps/cli/src/components/screens/cookie-sync-confirm-screen.tsx b/apps/cli/src/components/screens/cookie-sync-confirm-screen.tsx
index ed26ead75..6a77f29e0 100644
--- a/apps/cli/src/components/screens/cookie-sync-confirm-screen.tsx
+++ b/apps/cli/src/components/screens/cookie-sync-confirm-screen.tsx
@@ -61,10 +61,16 @@ export const CookieSyncConfirmScreen = ({
   const confirm = () => {
     const keys = [...selectedKeys];
     setCookieBrowserKeys(keys);
-    trackEvent("cookies:browser_selection", {
-      selected_count: keys.length,
-      browsers: keys.join(","),
+    trackEvent("cookies:sync_choice", {
+      choice: keys.length > 0 ? "use_cookies" : "skip_cookies",
     });
+    if (keys.length > 0) {
+      trackEvent("cookies:browser_selection", {
+        selected_count: keys.length,
+        browsers: keys.join(","),
+      });
+      trackEvent("cookies:toggled", { enabled: true });
+    }
     if (changesFor && instruction) {
       setScreen(
         screenForTestingOrPortPicker({
diff --git a/apps/cli/src/components/screens/main-menu-screen.tsx b/apps/cli/src/components/screens/main-menu-screen.tsx
index afe77137b..a748a0683 100644
--- a/apps/cli/src/components/screens/main-menu-screen.tsx
+++ b/apps/cli/src/components/screens/main-menu-screen.tsx
@@ -234,6 +234,7 @@ export const MainMenu = ({ gitState }: MainMenuProps) => {
         if (cookieBrowserKeys.length > 0) {
           clearCookieBrowserKeys();
           trackEvent("cookies:cleared");
+          trackEvent("cookies:toggled", { enabled: false });
         } else {
           setScreen(Screen.CookieSyncConfirm({}));
         }
diff --git a/apps/cli/src/data/execution-atom.ts b/apps/cli/src/data/execution-atom.ts
index 13bd79384..0a8d323bf 100644
--- a/apps/cli/src/data/execution-atom.ts
+++ b/apps/cli/src/data/execution-atom.ts
@@ -189,7 +189,16 @@ export const executeFn = cliAtomRuntime.fn<ExecuteInput>()((input) =>
     Effect.tapError((error) =>
       Effect.gen(function* () {
         const analytics = yield* Analytics;
-        const errorTag = error instanceof Error ? error.constructor.name : "UnknownError";
+        const errorTag =
+          typeof error === "object" &&
+          error !== null &&
+          "_tag" in error &&
+          typeof error._tag === "string"
+            ? error._tag
+            : // ignore for now
+              (error as any) instanceof Error
+              ? (error as any).constructor.name
+              : "UnknownError";
         yield* analytics.capture("run:failed", {
           plan_id: "direct",
           error_tag: errorTag,