diff --git a/apps/dashboard/src/app/(dashboard)/settings/billing/client.tsx b/apps/dashboard/src/app/(dashboard)/settings/billing/client.tsx
index ea00748da..ff3f8b425 100644
--- a/apps/dashboard/src/app/(dashboard)/settings/billing/client.tsx
+++ b/apps/dashboard/src/app/(dashboard)/settings/billing/client.tsx
@@ -84,6 +84,7 @@ export function Client() {
   const { data: workspace } = useQuery(trpc.workspace.get.queryOptions());
   // Captured on mount: the toasts clear the params while the dialog is open.
   const [askIntent, setAskIntent] = useState(Boolean(success || trial));
+  const [startedTrial] = useState(Boolean(trial));
   const { data: hasIntent } = useQuery({
     ...trpc.feedback.hasSubmitted.queryOptions({ source: "upgrade-intent" }),
     enabled: askIntent,
@@ -167,7 +168,14 @@ export function Client() {
         }
         await new Promise((resolve) => setTimeout(resolve, 1_000));
       }
-      if (!cancelled) setSearchParams({ trial: null });
+      if (cancelled) return;
+      // Webhook still pending: confirm checkout without claiming the trial.
+      toast.success("Checkout complete", {
+        description: "Your trial starts as soon as Stripe confirms it.",
+        duration: 5_000,
+        onAutoClose: () => setSearchParams({ trial: null }),
+        onDismiss: () => setSearchParams({ trial: null }),
+      });
     })();
     return () => {
       cancelled = true;
@@ -212,6 +220,7 @@ export function Client() {
       <UpgradeIntentDialog
         open={askIntent && hasIntent === false}
         onOpenChange={setAskIntent}
+        trial={startedTrial}
       />
       <Section>
         <SectionHeader>
diff --git a/apps/dashboard/src/components/dialogs/upgrade-intent.tsx b/apps/dashboard/src/components/dialogs/upgrade-intent.tsx
index b2b424c7b..b4c866893 100644
--- a/apps/dashboard/src/components/dialogs/upgrade-intent.tsx
+++ b/apps/dashboard/src/components/dialogs/upgrade-intent.tsx
@@ -1,5 +1,6 @@
 "use client";
 
+import { TRIAL_DAYS } from "@openstatus/api/src/router/stripe/trial-config";
 import { Button } from "@openstatus/ui/components/ui/button";
 import {
   Dialog,
@@ -19,7 +20,10 @@ import { toast } from "sonner";
 import { useTRPC } from "@/lib/trpc/client";
 
 /** Asked after an upgrade or trial start; stored as `upgrade-intent` feedback. */
-export function UpgradeIntentDialog(props: DialogProps) {
+export function UpgradeIntentDialog({
+  trial,
+  ...props
+}: DialogProps & { trial?: boolean }) {
   const trpc = useTRPC();
   const queryClient = useQueryClient();
   const id = useId();
@@ -45,6 +49,9 @@ export function UpgradeIntentDialog(props: DialogProps) {
         <DialogHeader>
           <DialogTitle>What are you using openstatus for?</DialogTitle>
           <DialogDescription>
+            {trial
+              ? `Your ${TRIAL_DAYS}-day Starter trial has started.`
+              : "Your plan is active."}{" "}
             A sentence or two helps us tailor openstatus to you.
           </DialogDescription>
         </DialogHeader>