From a8f1bd6e74734cc5d6b07edcd1a62be9cfde0596 Mon Sep 17 00:00:00 2001
From: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>
Date: Thu, 22 Jan 2026 14:40:32 +0000
Subject: [PATCH 1/3] fix: harmonize account settings between browser and
 desktop app

- Add subscription_status and trial_end claims to JWT via auth hook
- Update desktop billing context to extract and expose subscription status
- Update account settings UI to show 'TRIAL' for trialing users instead of 'PRO'
- Add trial end date display when available
- Export SubscriptionStatus type from @hypr/supabase package

This fixes the discrepancy where browser showed 'Trial' but desktop showed 'PRO'
for users on trial subscriptions.

Co-Authored-By: john@hyprnote.com <john@hyprnote.com>
---
 apps/desktop/src/billing.tsx                  | 64 +++++++++++++++-
 .../components/settings/general/account.tsx   | 18 ++++-
 packages/supabase/src/index.ts                |  2 +-
 packages/supabase/src/jwt.ts                  | 12 +++
 ...2000001_add_subscription_claims_to_jwt.sql | 73 +++++++++++++++++++
 5 files changed, 162 insertions(+), 7 deletions(-)
 create mode 100644 supabase/migrations/20250122000001_add_subscription_claims_to_jwt.sql

diff --git a/apps/desktop/src/billing.tsx b/apps/desktop/src/billing.tsx
index bb01cd3a47..dc3c932ff0 100644
--- a/apps/desktop/src/billing.tsx
+++ b/apps/desktop/src/billing.tsx
@@ -11,23 +11,53 @@ import {
 import { getRpcCanStartTrial } from "@hypr/api-client";
 import { createClient } from "@hypr/api-client/client";
 import { commands as openerCommands } from "@hypr/plugin-opener2";
+import type { SubscriptionStatus } from "@hypr/supabase";
 
 import { useAuth } from "./auth";
 import { env } from "./env";
 import { getScheme } from "./utils";
 
+type JwtClaims = {
+  entitlements?: string[];
+  subscription_status?: SubscriptionStatus;
+  trial_end?: number;
+};
+
 export function getEntitlementsFromToken(accessToken: string): string[] {
   try {
-    const decoded = jwtDecode<{ entitlements?: string[] }>(accessToken);
+    const decoded = jwtDecode<JwtClaims>(accessToken);
     return decoded.entitlements ?? [];
   } catch {
     return [];
   }
 }
 
+export function getSubscriptionStatusFromToken(
+  accessToken: string,
+): SubscriptionStatus | undefined {
+  try {
+    const decoded = jwtDecode<JwtClaims>(accessToken);
+    return decoded.subscription_status;
+  } catch {
+    return undefined;
+  }
+}
+
+export function getTrialEndFromToken(accessToken: string): number | undefined {
+  try {
+    const decoded = jwtDecode<JwtClaims>(accessToken);
+    return decoded.trial_end;
+  } catch {
+    return undefined;
+  }
+}
+
 type BillingContextValue = {
   entitlements: string[];
   isPro: boolean;
+  subscriptionStatus: SubscriptionStatus;
+  isOnTrial: boolean;
+  trialEnd: number | undefined;
   canStartTrial: boolean;
   upgradeToPro: () => void;
 };
@@ -46,11 +76,30 @@ export function BillingProvider({ children }: { children: ReactNode }) {
     return getEntitlementsFromToken(auth.session.access_token);
   }, [auth?.session?.access_token]);
 
+  const subscriptionStatus = useMemo<SubscriptionStatus>(() => {
+    if (!auth?.session?.access_token) {
+      return "none";
+    }
+    return getSubscriptionStatusFromToken(auth.session.access_token) ?? "none";
+  }, [auth?.session?.access_token]);
+
+  const trialEnd = useMemo(() => {
+    if (!auth?.session?.access_token) {
+      return undefined;
+    }
+    return getTrialEndFromToken(auth.session.access_token);
+  }, [auth?.session?.access_token]);
+
   const isPro = useMemo(
     () => entitlements.includes("hyprnote_pro"),
     [entitlements],
   );
 
+  const isOnTrial = useMemo(
+    () => subscriptionStatus === "trialing",
+    [subscriptionStatus],
+  );
+
   const canTrialQuery = useQuery({
     enabled: !!auth?.session && !isPro,
     queryKey: [auth?.session?.user.id ?? "", "canStartTrial"],
@@ -82,10 +131,21 @@ export function BillingProvider({ children }: { children: ReactNode }) {
     () => ({
       entitlements,
       isPro,
+      subscriptionStatus,
+      isOnTrial,
+      trialEnd,
       canStartTrial,
       upgradeToPro,
     }),
-    [entitlements, isPro, canStartTrial, upgradeToPro],
+    [
+      entitlements,
+      isPro,
+      subscriptionStatus,
+      isOnTrial,
+      trialEnd,
+      canStartTrial,
+      upgradeToPro,
+    ],
   );
 
   return (
diff --git a/apps/desktop/src/components/settings/general/account.tsx b/apps/desktop/src/components/settings/general/account.tsx
index c66cde8e22..b7763ed4a4 100644
--- a/apps/desktop/src/components/settings/general/account.tsx
+++ b/apps/desktop/src/components/settings/general/account.tsx
@@ -19,7 +19,7 @@ const WEB_APP_BASE_URL = env.VITE_APP_URL ?? "http://localhost:3000";
 
 export function AccountSettings() {
   const auth = useAuth();
-  const { isPro } = useBillingAccess();
+  const { isPro, isOnTrial, trialEnd } = useBillingAccess();
   const store = settings.UI.useStore(settings.STORE_ID);
 
   const isAuthenticated = !!auth?.session;
@@ -171,7 +171,17 @@ export function AccountSettings() {
 
       <Container
         title="Plan & Billing"
-        description={`Your current plan is ${isPro ? "PRO" : "FREE"}. `}
+        description={`Your current plan is ${
+          isOnTrial
+            ? `TRIAL${
+                trialEnd
+                  ? ` (ends ${new Date(trialEnd * 1000).toLocaleDateString()})`
+                  : ""
+              }`
+            : isPro
+              ? "PRO"
+              : "FREE"
+        }. `}
         action={<BillingButton />}
       >
         <p className="text-sm text-neutral-600">
@@ -191,7 +201,7 @@ export function AccountSettings() {
 
 function BillingButton() {
   const auth = useAuth();
-  const { isPro } = useBillingAccess();
+  const { isPro, isOnTrial } = useBillingAccess();
   const { open: openTrialBeginModal } = useTrialBeginModal();
 
   const canTrialQuery = useQuery({
@@ -262,7 +272,7 @@ function BillingButton() {
     void openerCommands.openUrl(`${WEB_APP_BASE_URL}/app/account`, null);
   }, []);
 
-  if (isPro) {
+  if (isPro || isOnTrial) {
     return (
       <Button
         variant="outline"
diff --git a/packages/supabase/src/index.ts b/packages/supabase/src/index.ts
index 3d35e384b6..864dd8c39b 100644
--- a/packages/supabase/src/index.ts
+++ b/packages/supabase/src/index.ts
@@ -3,5 +3,5 @@ export type { SupabaseClient } from "@supabase/supabase-js";
 
 export { createRemoteJWKSet, jwtVerify } from "jose";
 
-export type { SupabaseJwtPayload } from "./jwt";
+export type { SubscriptionStatus, SupabaseJwtPayload } from "./jwt";
 export { createJwksVerifier } from "./jwt";
diff --git a/packages/supabase/src/jwt.ts b/packages/supabase/src/jwt.ts
index 48fb606cc1..2985be46a6 100644
--- a/packages/supabase/src/jwt.ts
+++ b/packages/supabase/src/jwt.ts
@@ -1,8 +1,20 @@
 import { createRemoteJWKSet, jwtVerify } from "jose";
 
+export type SubscriptionStatus =
+  | "none"
+  | "active"
+  | "trialing"
+  | "past_due"
+  | "canceled"
+  | "incomplete"
+  | "incomplete_expired"
+  | "unpaid";
+
 export type SupabaseJwtPayload = {
   sub?: string;
   entitlements?: string[];
+  subscription_status?: SubscriptionStatus;
+  trial_end?: number;
 };
 
 export type JwksVerifier = {
diff --git a/supabase/migrations/20250122000001_add_subscription_claims_to_jwt.sql b/supabase/migrations/20250122000001_add_subscription_claims_to_jwt.sql
new file mode 100644
index 0000000000..2a601f1f38
--- /dev/null
+++ b/supabase/migrations/20250122000001_add_subscription_claims_to_jwt.sql
@@ -0,0 +1,73 @@
+-- Add subscription status and trial information to JWT claims
+-- This allows the desktop app to distinguish between trial and paid pro users
+
+CREATE OR REPLACE FUNCTION public.custom_access_token_hook(event jsonb)
+RETURNS jsonb
+LANGUAGE plpgsql
+STABLE
+AS $$
+DECLARE
+  claims jsonb;
+  entitlements jsonb := '[]'::jsonb;
+  subscription_status text := 'none';
+  trial_end_ts bigint := NULL;
+  user_stripe_customer_id text;
+BEGIN
+  -- Get user's stripe customer ID
+  SELECT stripe_customer_id INTO user_stripe_customer_id
+  FROM public.profiles
+  WHERE id = (event->>'user_id')::uuid;
+
+  -- Get entitlements
+  SELECT
+    COALESCE(
+      jsonb_agg(ae.lookup_key ORDER BY ae.lookup_key)
+        FILTER (WHERE ae.lookup_key IS NOT NULL),
+      '[]'::jsonb
+    )
+  INTO entitlements
+  FROM stripe.active_entitlements ae
+  WHERE ae.customer = user_stripe_customer_id;
+
+  -- Get subscription status and trial end date if exists
+  IF user_stripe_customer_id IS NOT NULL THEN
+    SELECT
+      s.status,
+      (s.trial_end #>> '{}')::bigint
+    INTO subscription_status, trial_end_ts
+    FROM stripe.subscriptions s
+    WHERE s.customer = user_stripe_customer_id
+      AND s.status IN ('active', 'trialing', 'past_due')
+    ORDER BY s.created DESC
+    LIMIT 1;
+
+    -- If no active subscription found, set status to 'none'
+    IF subscription_status IS NULL THEN
+      subscription_status := 'none';
+    END IF;
+  END IF;
+
+  -- Build claims
+  claims := event->'claims';
+  claims := jsonb_set(claims, '{entitlements}', entitlements);
+  claims := jsonb_set(claims, '{subscription_status}', to_jsonb(subscription_status));
+
+  -- Only add trial_end if it exists
+  IF trial_end_ts IS NOT NULL THEN
+    claims := jsonb_set(claims, '{trial_end}', to_jsonb(trial_end_ts));
+  END IF;
+
+  event := jsonb_set(event, '{claims}', claims);
+
+  RETURN event;
+END;
+$$;
+
+-- Grant necessary permissions for the new subscription query
+GRANT SELECT ON TABLE stripe.subscriptions TO supabase_auth_admin;
+
+CREATE POLICY "Allow auth admin to read subscriptions"
+ON stripe.subscriptions
+AS PERMISSIVE FOR SELECT
+TO supabase_auth_admin
+USING (true);

From d63969d10fde9ddba02080197edbe1420eb47f92 Mon Sep 17 00:00:00 2001
From: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>
Date: Thu, 22 Jan 2026 14:45:50 +0000
Subject: [PATCH 2/3] fix: define SubscriptionStatus type locally instead of
 importing from @hypr/supabase

The desktop app doesn't have @hypr/supabase as a dependency, so we define
the SubscriptionStatus type locally to avoid the 'Cannot find module' error.

Co-Authored-By: john@hyprnote.com <john@hyprnote.com>
---
 apps/desktop/src/billing.tsx | 11 ++++++++++-
 1 file changed, 10 insertions(+), 1 deletion(-)

diff --git a/apps/desktop/src/billing.tsx b/apps/desktop/src/billing.tsx
index dc3c932ff0..dc29cacd3c 100644
--- a/apps/desktop/src/billing.tsx
+++ b/apps/desktop/src/billing.tsx
@@ -11,12 +11,21 @@ import {
 import { getRpcCanStartTrial } from "@hypr/api-client";
 import { createClient } from "@hypr/api-client/client";
 import { commands as openerCommands } from "@hypr/plugin-opener2";
-import type { SubscriptionStatus } from "@hypr/supabase";
 
 import { useAuth } from "./auth";
 import { env } from "./env";
 import { getScheme } from "./utils";
 
+type SubscriptionStatus =
+  | "none"
+  | "active"
+  | "trialing"
+  | "past_due"
+  | "canceled"
+  | "incomplete"
+  | "incomplete_expired"
+  | "unpaid";
+
 type JwtClaims = {
   entitlements?: string[];
   subscription_status?: SubscriptionStatus;

From 072432c59ef35e84c87fb145a2ed93166c56733a Mon Sep 17 00:00:00 2001
From: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>
Date: Thu, 22 Jan 2026 15:09:05 +0000
Subject: [PATCH 3/3] fix: prioritize active subscription over trialing in web
 billing sync

The syncAfterSuccess function was returning the first subscription found
(sorted by creation date) regardless of status. This could return a
canceled or old trialing subscription instead of the active one.

Now it explicitly searches for 'active' subscriptions first, then falls
back to 'trialing' if no active subscription exists. This ensures paid
Pro users see 'Pro' instead of 'Trial' in their web account settings.

Co-Authored-By: john@hyprnote.com <john@hyprnote.com>
---
 apps/web/src/functions/billing.ts | 18 ++++++++++--------
 1 file changed, 10 insertions(+), 8 deletions(-)

diff --git a/apps/web/src/functions/billing.ts b/apps/web/src/functions/billing.ts
index aa99544af8..193c26b2ce 100644
--- a/apps/web/src/functions/billing.ts
+++ b/apps/web/src/functions/billing.ts
@@ -196,21 +196,23 @@ export const syncAfterSuccess = createServerFn({ method: "POST" }).handler(
 
     const subscriptions = await stripe.subscriptions.list({
       customer: stripeCustomerId,
-      limit: 1,
       status: "all",
     });
 
-    if (subscriptions.data.length === 0) {
+    // Find the first active or trialing subscription (prioritize active over trialing)
+    const activeSubscription =
+      subscriptions.data.find((sub) => sub.status === "active") ||
+      subscriptions.data.find((sub) => sub.status === "trialing");
+
+    if (!activeSubscription) {
       return { status: "none" };
     }
 
-    const subscription = subscriptions.data[0];
-
     return {
-      subscriptionId: subscription.id,
-      status: subscription.status,
-      priceId: subscription.items.data[0].price.id,
-      cancelAtPeriodEnd: subscription.cancel_at_period_end,
+      subscriptionId: activeSubscription.id,
+      status: activeSubscription.status,
+      priceId: activeSubscription.items.data[0].price.id,
+      cancelAtPeriodEnd: activeSubscription.cancel_at_period_end,
     };
   },
 );