diff --git a/apps/api/src/controllers/webhook.controller.ts b/apps/api/src/controllers/webhook.controller.ts
index 401e45aca..694003e51 100644
--- a/apps/api/src/controllers/webhook.controller.ts
+++ b/apps/api/src/controllers/webhook.controller.ts
@@ -148,6 +148,7 @@ const TRACKED_SUBSCRIPTION_FIELDS = [
   'subscriptionPeriodEventsLimit',
   'subscriptionPauseAtPeriodEnd',
   'subscriptionResumesAt',
+  'subscriptionFirstStartedAt',
 ] as const;
 
 const CANCELLATION_REASONS = [
@@ -302,6 +303,12 @@ async function syncSubscriptionToOrg(
     subscriptionCancelComment: data.customerCancellationComment ?? null,
     subscriptionPauseAtPeriodEnd: data.pauseAtPeriodEnd,
     subscriptionResumesAt: data.resumesAt,
+    // Stable tenure anchor: keep the stored value while the subscription id is
+    // unchanged; a new subscription (re-subscribe) restarts tenure.
+    subscriptionFirstStartedAt:
+      organization.subscriptionId === data.id
+        ? (organization.subscriptionFirstStartedAt ?? data.createdAt)
+        : data.createdAt,
     subscriptionPeriodEventsLimit,
     subscriptionPeriodEventsCountExceededAt:
       typeof subscriptionPeriodEventsLimit === 'number' &&
diff --git a/apps/public/src/app/(home)/_sections/pricing.tsx b/apps/public/src/app/(home)/_sections/pricing.tsx
index 10669f851..476e18467 100644
--- a/apps/public/src/app/(home)/_sections/pricing.tsx
+++ b/apps/public/src/app/(home)/_sections/pricing.tsx
@@ -79,6 +79,9 @@ export function Pricing() {
                     + VAT if applicable
                   </span>
                 </div>
+                <span className="mt-2 text-emerald-600 text-sm dark:text-emerald-500">
+                  Pay yearly and get 2 months free
+                </span>
               </>
             ) : (
               <div className="text-lg">
diff --git a/apps/public/src/components/pricing-slider.tsx b/apps/public/src/components/pricing-slider.tsx
index b557f8802..31a52c772 100644
--- a/apps/public/src/components/pricing-slider.tsx
+++ b/apps/public/src/components/pricing-slider.tsx
@@ -49,6 +49,9 @@ export function PricingSlider() {
           >
             + VAT if applicable
           </span>
+          <div className="mt-1 text-emerald-600 text-sm dark:text-emerald-500">
+            Pay yearly and get 2 months free
+          </div>
         </div>
       ) : (
         <div className="text-lg">
diff --git a/apps/start/src/components/organization/billing-plan-picker.tsx b/apps/start/src/components/organization/billing-plan-picker.tsx
index 9bdc4c61a..72f55e583 100644
--- a/apps/start/src/components/organization/billing-plan-picker.tsx
+++ b/apps/start/src/components/organization/billing-plan-picker.tsx
@@ -20,6 +20,7 @@ interface Props {
   organization: IServiceOrganization;
   currentProduct: IPolarProduct | null;
   onComplete?: () => void;
+  defaultInterval?: 'year' | 'month';
 }
 
 const getPrice = (product: IPolarProduct) => {
@@ -32,6 +33,7 @@ export default function BillingPlanPicker({
   organization,
   currentProduct,
   onComplete,
+  defaultInterval,
 }: Props) {
   const number = useNumber();
   const trpc = useTRPC();
@@ -41,16 +43,25 @@ export default function BillingPlanPicker({
       organizationId: organization.id,
     }),
   );
+  // Yearly is the default for new subscribers — it churns far less and saves
+  // them 2 months. Existing subscribers land on their current interval.
   const [recurringInterval, setRecurringInterval] = useState<'year' | 'month'>(
-    (organization.subscriptionInterval as 'year' | 'month') || 'month',
+    defaultInterval ??
+      ((organization.subscriptionInterval as 'year' | 'month') || 'year'),
   );
   const [selectedProductId, setSelectedProductId] = useState<string | null>(
     organization.subscriptionProductId || null,
   );
   const [pendingProductId, setPendingProductId] = useState<string | null>(null);
   const products = productsQuery.data || [];
+  // Only treat a product as selected while it belongs to the displayed
+  // interval. Opening the picker preset to yearly for a monthly subscriber
+  // (or toggling the interval) must not keep the monthly plan "selected" —
+  // that would render the cancel action under a list it isn't part of.
   const selectedProduct = products.find(
-    (product) => product.id === selectedProductId,
+    (product) =>
+      product.id === selectedProductId &&
+      product.recurringInterval === recurringInterval,
   );
 
   // No current plan to compare against → a plan row is the buy button (straight
@@ -243,7 +254,13 @@ export default function BillingPlanPicker({
         <div className="row items-center justify-between gap-2 -mb-2">
           <div className="font-medium">
             {recurringInterval === 'year' ? (
-              'Switch to monthly'
+              <>
+                Yearly billing —{' '}
+                <span className="text-emerald-500">2 months free</span>{' '}
+                <span className="text-muted-foreground font-normal">
+                  (pay for 10 months, get 12)
+                </span>
+              </>
             ) : (
               <>
                 Switch to yearly and get{' '}
@@ -310,7 +327,12 @@ export default function BillingPlanPicker({
               >
                 <span className={'font-medium'}>{product.name}</span>
                 <div className="row items-center gap-2">
-                  <span className="font-bold">{number.currency(price)}</span>
+                  <span className="font-bold">
+                    {number.currency(price)}
+                    <span className="font-normal text-muted-foreground">
+                      /{recurringInterval === 'year' ? 'yr' : 'mo'}
+                    </span>
+                  </span>
                   {renderRowIndicator(product)}
                 </div>
               </button>
diff --git a/apps/start/src/components/organization/yearly-switch-prompt.tsx b/apps/start/src/components/organization/yearly-switch-prompt.tsx
new file mode 100644
index 000000000..bab8973d9
--- /dev/null
+++ b/apps/start/src/components/organization/yearly-switch-prompt.tsx
@@ -0,0 +1,105 @@
+import type { IServiceOrganization } from '@openpanel/db';
+import { useQuery } from '@tanstack/react-query';
+import { differenceInMonths } from 'date-fns';
+import { useEffect, useState } from 'react';
+import { Button } from '@/components/ui/button';
+import { useTRPC } from '@/integrations/trpc/react';
+import { pushModal } from '@/modals';
+import { op } from '@/utils/op';
+
+// Yearly plans churn a fraction of monthly ones. Nudge monthly subscribers who
+// have stuck around for a while to switch — they get 2 months free, we keep
+// them longer. Dismissal is per-org and per-browser.
+const MIN_TENURE_MONTHS = 3;
+
+const dismissKey = (organizationId: string) =>
+  `op-yearly-prompt-dismissed:${organizationId}`;
+
+const readDismissed = (organizationId: string) => {
+  try {
+    return localStorage.getItem(dismissKey(organizationId)) === '1';
+  } catch {
+    return true;
+  }
+};
+
+export default function YearlySwitchPrompt({
+  organization,
+}: {
+  organization: IServiceOrganization;
+}) {
+  const trpc = useTRPC();
+  // Hidden until mounted so SSR and the first client render agree.
+  const [dismissed, setDismissed] = useState(true);
+  useEffect(() => {
+    setDismissed(readDismissed(organization.id));
+  }, [organization.id]);
+
+  const eligible =
+    organization.subscriptionState === 'active' &&
+    organization.subscriptionInterval === 'month' &&
+    !!organization.subscriptionFirstStartedAt &&
+    differenceInMonths(new Date(), organization.subscriptionFirstStartedAt) >=
+      MIN_TENURE_MONTHS;
+
+  const accessQuery = useQuery(
+    trpc.organization.myAccess.queryOptions(
+      { organizationId: organization.id },
+      { enabled: eligible && !dismissed }
+    )
+  );
+  const isAdmin = accessQuery.data?.role === 'org:admin';
+
+  const currentProductQuery = useQuery(
+    trpc.subscription.getCurrent.queryOptions(
+      { organizationId: organization.id },
+      { enabled: eligible && !dismissed && isAdmin }
+    )
+  );
+
+  if (!(eligible && isAdmin) || dismissed) {
+    return null;
+  }
+
+  const dismiss = () => {
+    op.track('yearly_prompt_dismissed', { organizationId: organization.id });
+    try {
+      localStorage.setItem(dismissKey(organization.id), '1');
+    } catch {
+      // Storage unavailable — the prompt just shows again next session.
+    }
+    setDismissed(true);
+  };
+
+  return (
+    <div className="col gap-1 border-b bg-card p-4 lg:p-8">
+      <div className="font-medium text-lg">
+        Switch to yearly — get 2 months free
+      </div>
+      <div className="mb-1">
+        You've been with us for a while. Pay for 10 months and get 12: same
+        plan, same limits, one invoice a year.
+      </div>
+      <div className="row gap-2">
+        <Button
+          loading={currentProductQuery.isLoading}
+          onClick={() => {
+            op.track('yearly_prompt_clicked', {
+              organizationId: organization.id,
+            });
+            pushModal('SelectBillingPlan', {
+              organization,
+              currentProduct: currentProductQuery.data ?? null,
+              defaultInterval: 'year',
+            });
+          }}
+        >
+          See my yearly price
+        </Button>
+        <Button onClick={dismiss} variant="outline">
+          Maybe later
+        </Button>
+      </div>
+    </div>
+  );
+}
diff --git a/apps/start/src/modals/select-billing-plan.tsx b/apps/start/src/modals/select-billing-plan.tsx
index 7ed8d93cd..ece9a5816 100644
--- a/apps/start/src/modals/select-billing-plan.tsx
+++ b/apps/start/src/modals/select-billing-plan.tsx
@@ -7,17 +7,20 @@ import BillingPlanPicker from '@/components/organization/billing-plan-picker';
 interface Props {
   organization: IServiceOrganization;
   currentProduct: IPolarProduct | null;
+  defaultInterval?: 'year' | 'month';
 }
 
 export default function SelectBillingPlan({
   organization,
   currentProduct,
+  defaultInterval,
 }: Props) {
   return (
     <ModalContent className="!flex !flex-col !overflow-hidden">
       <ModalHeader title="Select a billing plan" />
       <BillingPlanPicker
         currentProduct={currentProduct}
+        defaultInterval={defaultInterval}
         onComplete={popModal}
         organization={organization}
       />
diff --git a/apps/start/src/routes/_app.$organizationId.tsx b/apps/start/src/routes/_app.$organizationId.tsx
index 0a442a72f..25d85e19d 100644
--- a/apps/start/src/routes/_app.$organizationId.tsx
+++ b/apps/start/src/routes/_app.$organizationId.tsx
@@ -2,6 +2,7 @@ import { FullPageEmptyState } from '@/components/full-page-empty-state';
 import FullPageLoadingState from '@/components/full-page-loading-state';
 import FeedbackPrompt from '@/components/organization/feedback-prompt';
 import SupporterPrompt from '@/components/organization/supporter-prompt';
+import YearlySwitchPrompt from '@/components/organization/yearly-switch-prompt';
 import { LinkButton } from '@/components/ui/button';
 import { useTRPC } from '@/integrations/trpc/react';
 import { cn } from '@/utils/cn';
@@ -138,8 +139,14 @@ function Component() {
     isProjectRoute &&
     subscriptionBlocksDashboard(organization.subscriptionState);
 
+  const location = useLocation();
+  const isBillingPage = /\/.+\/billing/.test(location.pathname);
+
   return (
     <>
+      {!stateMeta.banner && !isBillingPage && (
+        <YearlySwitchPrompt organization={organization} />
+      )}
       {stateMeta.banner && !hideBannerForPrompt && (
         <Alert
           title={stateMeta.banner.title}
diff --git a/packages/db/prisma/migrations/20260822100000_subscription_first_started_at/migration.sql b/packages/db/prisma/migrations/20260822100000_subscription_first_started_at/migration.sql
new file mode 100644
index 000000000..67e08a2ca
--- /dev/null
+++ b/packages/db/prisma/migrations/20260822100000_subscription_first_started_at/migration.sql
@@ -0,0 +1,6 @@
+-- Stable subscription-creation timestamp for tenure. subscriptionStartsAt is
+-- overwritten with the current period start on every renewal, so it cannot
+-- answer "how long has this customer been subscribed" — this column can.
+-- Backfilled from Polar via packages/payments/scripts/sync-subscriptions.ts.
+ALTER TABLE "organizations"
+  ADD COLUMN "subscriptionFirstStartedAt" TIMESTAMP(3);
diff --git a/packages/db/prisma/schema.prisma b/packages/db/prisma/schema.prisma
index bd6f593cc..f310d2158 100644
--- a/packages/db/prisma/schema.prisma
+++ b/packages/db/prisma/schema.prisma
@@ -110,6 +110,10 @@ model Organization {
   // until the period ends, then flips to `paused`.
   subscriptionPauseAtPeriodEnd            Boolean   @default(false)
   subscriptionResumesAt                   DateTime?
+  // When the current Polar subscription was first created. Unlike
+  // subscriptionStartsAt (overwritten with each period start on renewal) this
+  // is stable, so it can measure tenure (e.g. the switch-to-yearly prompt).
+  subscriptionFirstStartedAt              DateTime?
 
   // When deleteAt > now(), the organization will be deleted
   deleteAt DateTime?
diff --git a/packages/payments/scripts/sync-subscriptions.ts b/packages/payments/scripts/sync-subscriptions.ts
index 28231a19d..9f881eb36 100644
--- a/packages/payments/scripts/sync-subscriptions.ts
+++ b/packages/payments/scripts/sync-subscriptions.ts
@@ -277,6 +277,10 @@ async function main() {
       subscriptionCreatedByUserId:
         metadataUserId ?? organization.subscriptionCreatedByUserId,
       subscriptionInterval: subscription.recurringInterval,
+      subscriptionFirstStartedAt:
+        organization.subscriptionId === subscription.id
+          ? (organization.subscriptionFirstStartedAt ?? subscription.createdAt)
+          : subscription.createdAt,
       subscriptionPeriodEventsLimit:
         subscriptionPeriodEventsLimit ?? organization.subscriptionPeriodEventsLimit,
       subscriptionPeriodEventsCountExceededAt:
@@ -299,6 +303,7 @@ async function main() {
       'subscriptionEndsAt',
       'subscriptionCreatedByUserId',
       'subscriptionInterval',
+      'subscriptionFirstStartedAt',
       'subscriptionPeriodEventsLimit',
     ] as const;