diff --git a/packages/backend/src/helpers/billing/webhooks.ee.ts b/packages/backend/src/helpers/billing/webhooks.ee.ts
index 056c754f..b9556d42 100644
--- a/packages/backend/src/helpers/billing/webhooks.ee.ts
+++ b/packages/backend/src/helpers/billing/webhooks.ee.ts
@@ -21,12 +21,11 @@ const handleSubscriptionCancelled = async (request: IRequest) => {
     .query()
     .findOne({
       paddle_subscription_id: request.body.subscription_id,
-    })
-    .patchAndFetch(formatSubscription(request));
+    });
 
-  if (request.body.status === 'deleted') {
-    await subscription.$query().delete();
-  }
+  await subscription.$query().patchAndFetch(formatSubscription(request));
+
+  await subscription.$query().delete();
 };
 
 const handleSubscriptionPaymentSucceeded = async (request: IRequest) => {
diff --git a/packages/web/src/components/CheckoutCompletedAlert/index.ee.tsx b/packages/web/src/components/CheckoutCompletedAlert/index.ee.tsx
new file mode 100644
index 00000000..c2f41f64
--- /dev/null
+++ b/packages/web/src/components/CheckoutCompletedAlert/index.ee.tsx
@@ -0,0 +1,30 @@
+import * as React from 'react';
+import { useLocation } from 'react-router-dom';
+import Alert from '@mui/material/Alert';
+import Typography from '@mui/material/Typography';
+
+import useFormatMessage from 'hooks/useFormatMessage';
+
+export default function CheckoutCompletedAlert() {
+  const formatMessage = useFormatMessage();
+  const location = useLocation();
+  const state = location.state as { checkoutCompleted: boolean };
+
+  const checkoutCompleted = state?.checkoutCompleted;
+
+  if (!checkoutCompleted) return <React.Fragment />;
+
+  return (
+    <Alert
+      severity="success"
+      sx={{
+        display: 'flex',
+        alignItems: 'center',
+      }}
+    >
+      <Typography variant="subtitle2" sx={{ lineHeight: 1.5 }}>
+        {formatMessage('checkoutCompletedAlert.text')}
+      </Typography>
+    </Alert>
+  );
+}
diff --git a/packages/web/src/components/UsageDataInformation/index.ee.tsx b/packages/web/src/components/UsageDataInformation/index.ee.tsx
index 7ff84a5d..275c8cc6 100644
--- a/packages/web/src/components/UsageDataInformation/index.ee.tsx
+++ b/packages/web/src/components/UsageDataInformation/index.ee.tsx
@@ -1,6 +1,5 @@
 import * as React from 'react';
 import { Link } from 'react-router-dom';
-import Alert from '@mui/material/Alert';
 import Stack from '@mui/material/Stack';
 import Box from '@mui/material/Box';
 import Button from '@mui/material/Button';
@@ -14,6 +13,7 @@ import Typography from '@mui/material/Typography';
 
 import { TBillingCardAction } from '@automatisch/types';
 import TrialOverAlert from 'components/TrialOverAlert/index.ee';
+import CheckoutCompletedAlert from 'components/CheckoutCompletedAlert/index.ee';
 import * as URLS from 'config/urls';
 import useBillingAndUsageData from 'hooks/useBillingAndUsageData.ee';
 import useFormatMessage from 'hooks/useFormatMessage';
@@ -98,6 +98,8 @@ export default function UsageDataInformation() {
     <React.Fragment>
       <Stack sx={{ width: '100%', mb: 2 }} spacing={2}>
         <TrialOverAlert />
+
+        <CheckoutCompletedAlert />
       </Stack>
       <Card sx={{ mb: 3, p: 2 }}>
         <CardContent sx={{ display: 'flex', flexDirection: 'column' }}>
diff --git a/packages/web/src/contexts/Paddle.ee.tsx b/packages/web/src/contexts/Paddle.ee.tsx
index 7eab8fc9..32deb155 100644
--- a/packages/web/src/contexts/Paddle.ee.tsx
+++ b/packages/web/src/contexts/Paddle.ee.tsx
@@ -1,7 +1,10 @@
 import * as React from 'react';
+import { useNavigate } from 'react-router-dom';
 
+import * as URLS from 'config/urls';
 import useCloud from 'hooks/useCloud';
 import usePaddleInfo from 'hooks/usePaddleInfo.ee';
+import apolloClient from 'graphql/client';
 
 declare global {
   interface Window {
@@ -27,9 +30,32 @@ export const PaddleProvider = (
 ): React.ReactElement => {
   const { children } = props;
   const isCloud = useCloud();
+  const navigate = useNavigate();
   const { sandbox, vendorId } = usePaddleInfo();
   const [loaded, setLoaded] = React.useState(false);
 
+  const paddleEventHandler = React.useCallback(async (payload) => {
+    const { event, eventData } = payload;
+    if (event === 'Checkout.Close') {
+      const completed = eventData.checkout?.completed;
+
+      if (completed) {
+        // Paddle has side effects in the background,
+        // so we need to refetch the relevant queries
+        await apolloClient.refetchQueries({
+          include: ['GetTrialStatus', 'GetBillingAndUsage'],
+        });
+
+        navigate(
+          URLS.SETTINGS_BILLING_AND_USAGE,
+          {
+            state: { checkoutCompleted: true }
+          }
+        );
+      }
+    }
+  }, [navigate]);
+
   const value = React.useMemo(() => {
     return {
       loaded,
@@ -69,8 +95,11 @@ export const PaddleProvider = (
       window.Paddle.Environment.set('sandbox');
     }
 
-    window.Paddle.Setup({ vendor: vendorId });
-  }, [loaded, sandbox, vendorId])
+    window.Paddle.Setup({
+      vendor: vendorId,
+      eventCallback: paddleEventHandler,
+    });
+  }, [loaded, sandbox, vendorId, paddleEventHandler])
 
   return (
     <PaddleContext.Provider value={value}>
diff --git a/packages/web/src/hooks/useBillingAndUsageData.ee.ts b/packages/web/src/hooks/useBillingAndUsageData.ee.ts
index 22dbb810..15ff6545 100644
--- a/packages/web/src/hooks/useBillingAndUsageData.ee.ts
+++ b/packages/web/src/hooks/useBillingAndUsageData.ee.ts
@@ -1,4 +1,6 @@
+import * as React from 'react';
 import { useQuery } from '@apollo/client';
+import { useLocation } from 'react-router-dom';
 import { DateTime } from 'luxon';
 import { TSubscription } from '@automatisch/types';
 
@@ -30,7 +32,23 @@ type UseBillingAndUsageDataReturn = {
 } | null;
 
 export default function useBillingAndUsageData(): UseBillingAndUsageDataReturn {
-  const { data, loading } = useQuery(GET_BILLING_AND_USAGE);
+  const location = useLocation();
+  const state = location.state as { checkoutCompleted: boolean };
+  const { data, loading, startPolling, stopPolling } = useQuery(GET_BILLING_AND_USAGE);
+  const checkoutCompleted = state?.checkoutCompleted;
+  const hasSubscription = !!data?.getBillingAndUsage?.subscription?.status;
+
+  React.useEffect(function pollDataUntilSubscriptionIsCreated() {
+    if (checkoutCompleted && !hasSubscription) {
+      startPolling(1000);
+    }
+  }, [checkoutCompleted, hasSubscription, startPolling]);
+
+  React.useEffect(function stopPollingWhenSubscriptionIsCreated() {
+    if (checkoutCompleted && hasSubscription) {
+      stopPolling();
+    }
+  }, [checkoutCompleted, hasSubscription, stopPolling]);
 
   if (loading) return null;
 
diff --git a/packages/web/src/hooks/useTrialStatus.ee.ts b/packages/web/src/hooks/useTrialStatus.ee.ts
index ece79ddd..edf67a96 100644
--- a/packages/web/src/hooks/useTrialStatus.ee.ts
+++ b/packages/web/src/hooks/useTrialStatus.ee.ts
@@ -1,4 +1,6 @@
+import * as React from 'react';
 import { useQuery } from '@apollo/client';
+import { useLocation } from 'react-router-dom';
 import { DateTime } from 'luxon';
 
 import { GET_TRIAL_STATUS } from 'graphql/queries/get-trial-status.ee';
@@ -48,7 +50,23 @@ function getFeedbackPayload(date: DateTime) {
 
 export default function useTrialStatus(): UseTrialStatusReturn {
   const formatMessage = useFormatMessage();
-  const { data, loading } = useQuery(GET_TRIAL_STATUS);
+  const location = useLocation();
+  const state = location.state as { checkoutCompleted: boolean };
+  const checkoutCompleted = state?.checkoutCompleted;
+  const { data, loading, startPolling, stopPolling } = useQuery(GET_TRIAL_STATUS);
+  const hasTrial = !!data?.getTrialStatus?.expireAt;
+
+  React.useEffect(function pollDataUntilTrialEnds() {
+    if (checkoutCompleted && hasTrial) {
+      startPolling(1000);
+    }
+  }, [checkoutCompleted, hasTrial, startPolling]);
+
+  React.useEffect(function stopPollingWhenTrialEnds() {
+    if (checkoutCompleted && !hasTrial) {
+      stopPolling();
+    }
+  }, [checkoutCompleted, hasTrial, stopPolling]);
 
   if (loading || !data.getTrialStatus) return null;
 
diff --git a/packages/web/src/locales/en.json b/packages/web/src/locales/en.json
index b4b7437e..22f19f9e 100644
--- a/packages/web/src/locales/en.json
+++ b/packages/web/src/locales/en.json
@@ -156,5 +156,6 @@
   "trialBadge.xDaysLeft": "{remainingDays} trial {remainingDays, plural, one {day} other {days}} left",
   "trialBadge.endsToday": "Trial ends today",
   "trialBadge.over": "Trial is over",
-  "trialOverAlert.text": "Your free trial is over. Please <link>upgrade</link> your plan to continue using Automatisch."
+  "trialOverAlert.text": "Your free trial is over. Please <link>upgrade</link> your plan to continue using Automatisch.",
+  "checkoutCompletedAlert.text": "Thank you for upgrading your subscription and supporting our self-funded business!"
 }