diff --git a/apps/desktop/src/components/onboarding/final.tsx b/apps/desktop/src/components/onboarding/final.tsx
index 4558e0b368..ab66919c66 100644
--- a/apps/desktop/src/components/onboarding/final.tsx
+++ b/apps/desktop/src/components/onboarding/final.tsx
@@ -14,6 +14,7 @@ import { Route } from "../../routes/app/onboarding/_layout.index";
 import * as settings from "../../store/tinybase/store/settings";
 import { commands } from "../../types/tauri.gen";
 import { configureProSettings } from "../../utils";
+import { pollForTrialActivation } from "../../utils/poll-trial-activation";
 import { getBack, type StepProps } from "./config";
 import { OnboardingContainer } from "./shared";
 
@@ -26,6 +27,10 @@ export function Final({ onNavigate }: StepProps) {
   const [isLoading, setIsLoading] = useState(true);
   const [trialStarted, setTrialStarted] = useState(false);
   const hasHandledRef = useRef(false);
+  const authRef = useRef(auth);
+  authRef.current = auth;
+  const storeRef = useRef(store);
+  storeRef.current = store;
 
   const backStep = getBack(search);
 
@@ -35,25 +40,33 @@ export function Final({ onNavigate }: StepProps) {
     }
     hasHandledRef.current = true;
 
+    const abortController = new AbortController();
+
     const handle = async () => {
-      if (!auth?.session) {
+      const currentAuth = authRef.current;
+      if (!currentAuth?.session) {
         setIsLoading(false);
         return;
       }
 
-      const headers = auth.getHeaders();
+      const headers = currentAuth.getHeaders();
       if (!headers) {
         setIsLoading(false);
         return;
       }
 
       try {
-        const started = await tryStartTrial(headers, store);
+        const started = await tryStartTrial(headers, storeRef.current);
         setTrialStarted(started);
         if (started) {
-          await new Promise((resolve) => setTimeout(resolve, 3000));
+          const result = await pollForTrialActivation({
+            refreshSession: () => authRef.current.refreshSession(),
+            signal: abortController.signal,
+          });
+          if (result.status === "aborted") return;
+        } else {
+          await authRef.current.refreshSession();
         }
-        await auth.refreshSession();
       } catch (e) {
         Sentry.captureException(e);
         console.error(e);
@@ -63,7 +76,12 @@ export function Final({ onNavigate }: StepProps) {
     };
 
     void handle();
-  }, [auth, store]);
+
+    return () => {
+      abortController.abort();
+    };
+    // eslint-disable-next-line react-hooks/exhaustive-deps
+  }, []);
 
   if (isLoading) {
     return (
diff --git a/apps/desktop/src/components/settings/general/account.tsx b/apps/desktop/src/components/settings/general/account.tsx
index f85865624d..230b76efca 100644
--- a/apps/desktop/src/components/settings/general/account.tsx
+++ b/apps/desktop/src/components/settings/general/account.tsx
@@ -1,4 +1,4 @@
-import { useMutation, useQuery } from "@tanstack/react-query";
+import { useQuery } from "@tanstack/react-query";
 import {
   Brain,
   Cloud,
@@ -9,7 +9,7 @@ import {
 } from "lucide-react";
 import { type ReactNode, useCallback, useEffect, useState } from "react";
 
-import { getRpcCanStartTrial, postBillingStartTrial } from "@hypr/api-client";
+import { getRpcCanStartTrial } from "@hypr/api-client";
 import { createClient } from "@hypr/api-client/client";
 import { commands as analyticsCommands } from "@hypr/plugin-analytics";
 import { type SubscriptionStatus } from "@hypr/plugin-auth";
@@ -22,6 +22,7 @@ import { cn } from "@hypr/utils";
 import { useAuth } from "../../../auth";
 import { useBillingAccess } from "../../../billing";
 import { env } from "../../../env";
+import { useTrialActivation } from "../../../hooks/useTrialActivation";
 
 const WEB_APP_BASE_URL = env.VITE_APP_URL ?? "http://localhost:3000";
 
@@ -333,41 +334,7 @@ function BillingButton() {
     },
   });
 
-  const startTrialMutation = useMutation({
-    mutationFn: async () => {
-      const headers = auth?.getHeaders();
-      if (!headers) {
-        throw new Error("Not authenticated");
-      }
-      const client = createClient({ baseUrl: env.VITE_API_URL, headers });
-      const { error } = await postBillingStartTrial({
-        client,
-        query: { interval: "monthly" },
-      });
-      if (error) {
-        throw error;
-      }
-
-      await new Promise((resolve) => setTimeout(resolve, 3000));
-    },
-    onSuccess: async () => {
-      void analyticsCommands.event({
-        event: "trial_started",
-        plan: "pro",
-      });
-      const trialEndDate = new Date();
-      trialEndDate.setDate(trialEndDate.getDate() + 14);
-      void analyticsCommands.setProperties({
-        email: auth?.session?.user.email,
-        user_id: auth?.session?.user.id,
-        set: {
-          plan: "pro",
-          trial_end_date: trialEndDate.toISOString(),
-        },
-      });
-      await auth?.refreshSession();
-    },
-  });
+  const { startTrial, isPending: isTrialPending } = useTrialActivation();
 
   const handleProUpgrade = useCallback(() => {
     void analyticsCommands.event({
@@ -401,8 +368,8 @@ function BillingButton() {
     return (
       <Button
         variant="outline"
-        onClick={() => startTrialMutation.mutate()}
-        disabled={startTrialMutation.isPending}
+        onClick={() => startTrial()}
+        disabled={isTrialPending}
       >
         <span> Start Pro Trial</span>
       </Button>
diff --git a/apps/desktop/src/hooks/useTrialActivation.ts b/apps/desktop/src/hooks/useTrialActivation.ts
new file mode 100644
index 0000000000..8a250b84bb
--- /dev/null
+++ b/apps/desktop/src/hooks/useTrialActivation.ts
@@ -0,0 +1,94 @@
+import { useMutation } from "@tanstack/react-query";
+import { useCallback, useEffect, useRef } from "react";
+
+import { postBillingStartTrial } from "@hypr/api-client";
+import { createClient } from "@hypr/api-client/client";
+import { commands as analyticsCommands } from "@hypr/plugin-analytics";
+
+import { useAuth } from "../auth";
+import { env } from "../env";
+import {
+  pollForTrialActivation,
+  type PollResult,
+} from "../utils/poll-trial-activation";
+
+type UseTrialActivationOptions = {
+  onActivated?: () => void;
+  onTimeout?: () => void;
+  onError?: (error: unknown) => void;
+};
+
+export function useTrialActivation(options: UseTrialActivationOptions = {}) {
+  const auth = useAuth();
+  const abortControllerRef = useRef<AbortController | null>(null);
+
+  useEffect(() => {
+    return () => {
+      abortControllerRef.current?.abort();
+    };
+  }, []);
+
+  const mutation = useMutation({
+    mutationFn: async (): Promise<PollResult> => {
+      const headers = auth?.getHeaders();
+      if (!headers) {
+        throw new Error("Not authenticated");
+      }
+
+      const client = createClient({ baseUrl: env.VITE_API_URL, headers });
+      const { error } = await postBillingStartTrial({
+        client,
+        query: { interval: "monthly" },
+      });
+      if (error) {
+        throw error;
+      }
+
+      abortControllerRef.current?.abort();
+      const abortController = new AbortController();
+      abortControllerRef.current = abortController;
+
+      return pollForTrialActivation({
+        refreshSession: () => auth.refreshSession(),
+        signal: abortController.signal,
+      });
+    },
+    onSuccess: (result) => {
+      if (result.status === "activated" || result.status === "timeout") {
+        void analyticsCommands.event({ event: "trial_started", plan: "pro" });
+        const trialEndDate = new Date();
+        trialEndDate.setDate(trialEndDate.getDate() + 14);
+        void analyticsCommands.setProperties({
+          email: auth?.session?.user.email,
+          user_id: auth?.session?.user.id,
+          set: {
+            plan: "pro",
+            trial_end_date: trialEndDate.toISOString(),
+          },
+        });
+        if (result.status === "activated") {
+          options.onActivated?.();
+        } else {
+          options.onTimeout?.();
+        }
+      }
+    },
+    onError: (error) => {
+      options.onError?.(error);
+    },
+  });
+
+  const cancel = useCallback(() => {
+    abortControllerRef.current?.abort();
+    abortControllerRef.current = null;
+  }, []);
+
+  return {
+    startTrial: mutation.mutate,
+    startTrialAsync: mutation.mutateAsync,
+    isPending: mutation.isPending,
+    isError: mutation.isError,
+    error: mutation.error,
+    cancel,
+  };
+}
diff --git a/apps/desktop/src/utils/poll-trial-activation.ts b/apps/desktop/src/utils/poll-trial-activation.ts
new file mode 100644
index 0000000000..d82c9d1289
--- /dev/null
+++ b/apps/desktop/src/utils/poll-trial-activation.ts
@@ -0,0 +1,74 @@
+import type { Session } from "@supabase/supabase-js";
+
+import { commands as authCommands } from "@hypr/plugin-auth";
+
+const INITIAL_DELAY_MS = 1000;
+const MAX_DELAY_MS = 5000;
+const BACKOFF_FACTOR = 1.5;
+const MAX_ATTEMPTS = 10;
+
+export type PollResult =
+  | { status: "activated"; session: Session }
+  | { status: "timeout" }
+  | { status: "aborted" };
+
+type PollOptions = {
+  refreshSession: () => Promise<Session | null>;
+  signal?: AbortSignal;
+};
+
+export async function pollForTrialActivation(
+  options: PollOptions,
+): Promise<PollResult> {
+  let delay = INITIAL_DELAY_MS;
+
+  for (let attempt = 0; attempt < MAX_ATTEMPTS; attempt++) {
+    if (options.signal?.aborted) {
+      return { status: "aborted" };
+    }
+
+    try {
+      await new Promise<void>((resolve, reject) => {
+        const timer = setTimeout(resolve, delay);
+        if (options.signal) {
+          const onAbort = () => {
+            clearTimeout(timer);
+            reject(new DOMException("Aborted", "AbortError"));
+          };
+          options.signal.addEventListener("abort", onAbort, { once: true });
+        }
+      });
+    } catch (e) {
+      if (e instanceof DOMException && e.name === "AbortError") {
+        return { status: "aborted" };
+      }
+      throw e;
+    }
+
+    if (options.signal?.aborted) {
+      return { status: "aborted" };
+    }
+
+    try {
+      const session = await options.refreshSession();
+      if (session) {
+        const result = await authCommands.decodeClaims(session.access_token);
+        if (result.status === "ok") {
+          const entitlements = result.data.entitlements ?? [];
+          if (entitlements.includes("hyprnote_pro")) {
+            return { status: "activated", session };
+          }
+        }
+      }
+    } catch (error) {
+      console.warn(
+        `Trial activation poll attempt ${attempt + 1} failed:`,
+        error,
+      );
+    }
+
+    delay = Math.min(delay * BACKOFF_FACTOR, MAX_DELAY_MS);
+  }
+
+  return { status: "timeout" };
+}