diff --git a/apps/web/src/app/api/stripe/webhook/route.ts b/apps/web/src/app/api/stripe/webhook/route.ts
index 07afbbeab..d5caef535 100644
--- a/apps/web/src/app/api/stripe/webhook/route.ts
+++ b/apps/web/src/app/api/stripe/webhook/route.ts
@@ -49,240 +49,270 @@ export async function POST(request: NextRequest) {
     );
   }
 
-  switch (event.type) {
-    case "checkout.session.completed": {
-      const checkoutSession = event.data.object as Stripe.Checkout.Session;
+  try {
+    switch (event.type) {
+      case "checkout.session.completed": {
+        const checkoutSession = event.data.object as Stripe.Checkout.Session;
 
-      if (checkoutSession.subscription === null) {
-        // This is a one-time payment (probably for Rallly Self-Hosted)
-        break;
-      }
+        if (checkoutSession.subscription === null) {
+          // This is a one-time payment (probably for Rallly Self-Hosted)
+          break;
+        }
 
-      const { userId } = checkoutMetadataSchema.parse(checkoutSession.metadata);
-
-      if (!userId) {
-        return NextResponse.json(
-          { error: "Missing client reference ID" },
-          { status: 400 },
+        const { userId } = checkoutMetadataSchema.parse(
+          checkoutSession.metadata,
         );
-      }
 
-      await prisma.user.update({
-        where: {
-          id: userId,
-        },
-        data: {
-          customerId: checkoutSession.customer as string,
-        },
-      });
+        if (!userId) {
+          return NextResponse.json(
+            { error: "Missing client reference ID" },
+            { status: 400 },
+          );
+        }
 
-      const subscription = await stripe.subscriptions.retrieve(
-        checkoutSession.subscription as string,
-      );
-
-      posthog?.capture({
-        distinctId: userId,
-        event: "upgrade",
-        properties: {
-          interval: subscription.items.data[0].plan.interval,
-          $set: {
-            tier: "pro",
+        await prisma.user.update({
+          where: {
+            id: userId,
           },
-        },
-      });
+          data: {
+            customerId: checkoutSession.customer as string,
+          },
+        });
 
-      break;
-    }
-    case "customer.subscription.deleted": {
-      const { id } = event.data.object as Stripe.Subscription;
-      const subscription = await stripe.subscriptions.retrieve(id);
-
-      // void any unpaid invoices
-      const invoices = await stripe.invoices.list({
-        subscription: subscription.id,
-        status: "open",
-      });
-
-      for (const invoice of invoices.data) {
-        await stripe.invoices.voidInvoice(invoice.id);
-      }
-
-      // delete the subscription from the database
-      await prisma.subscription.delete({
-        where: {
-          id: subscription.id,
-        },
-      });
-
-      try {
-        const { userId } = subscriptionMetadataSchema.parse(
-          subscription.metadata,
+        const subscription = await stripe.subscriptions.retrieve(
+          checkoutSession.subscription as string,
         );
 
         posthog?.capture({
           distinctId: userId,
-          event: "subscription cancel",
+          event: "upgrade",
           properties: {
+            interval: subscription.items.data[0].price.recurring?.interval,
             $set: {
-              tier: "hobby",
+              tier: "pro",
             },
           },
         });
-      } catch (e) {
-        Sentry.captureException(e);
+
+        break;
       }
+      case "customer.subscription.deleted": {
+        const { id } = event.data.object as Stripe.Subscription;
+        const subscription = await stripe.subscriptions.retrieve(id);
 
-      break;
-    }
-    case "customer.subscription.updated":
-    case "customer.subscription.created": {
-      const { id } = event.data.object as Stripe.Subscription;
+        // void any unpaid invoices
+        const invoices = await stripe.invoices.list({
+          subscription: subscription.id,
+          status: "open",
+        });
 
-      const subscription = await stripe.subscriptions.retrieve(id);
+        for (const invoice of invoices.data) {
+          await stripe.invoices.voidInvoice(invoice.id);
+        }
 
-      // check if the subscription is active
-      const isActive =
-        subscription.status === "active" ||
-        subscription.status === "trialing" ||
-        subscription.status === "past_due";
+        // delete the subscription from the database
+        await prisma.subscription.delete({
+          where: {
+            id: subscription.id,
+          },
+        });
 
-      // get the subscription price details
-      const lineItem = subscription.items.data[0];
+        try {
+          const { userId } = subscriptionMetadataSchema.parse(
+            subscription.metadata,
+          );
 
-      // update/create the subscription in the database
-      const { price } = lineItem;
+          posthog?.capture({
+            distinctId: userId,
+            event: "subscription cancel",
+            properties: {
+              $set: {
+                tier: "hobby",
+              },
+            },
+          });
+        } catch (e) {
+          Sentry.captureException(e);
+        }
 
-      const res = subscriptionMetadataSchema.safeParse(subscription.metadata);
-
-      if (!res.success) {
-        return NextResponse.json({ error: "Missing user ID" }, { status: 400 });
+        break;
       }
+      case "customer.subscription.updated":
+      case "customer.subscription.created": {
+        const { id } = event.data.object as Stripe.Subscription;
 
-      // create or update the subscription in the database
-      await prisma.subscription.upsert({
-        where: {
-          id: subscription.id,
-        },
-        create: {
-          id: subscription.id,
-          active: isActive,
-          priceId: price.id,
-          currency: subscription.currency ?? null,
-          createdAt: toDate(subscription.created),
-          periodStart: toDate(subscription.current_period_start),
-          periodEnd: toDate(subscription.current_period_end),
-        },
-        update: {
-          active: isActive,
-          priceId: price.id,
-          currency: subscription.currency ?? null,
-          createdAt: toDate(subscription.created),
-          periodStart: toDate(subscription.current_period_start),
-          periodEnd: toDate(subscription.current_period_end),
-        },
-      });
+        const subscription = await stripe.subscriptions.retrieve(id);
 
-      // update the user with the subscription id
-      await prisma.user.update({
-        where: {
-          id: res.data.userId,
-        },
-        data: {
-          subscriptionId: subscription.id,
-        },
-      });
+        // check if the subscription is active
+        const isActive =
+          subscription.status === "active" ||
+          subscription.status === "trialing" ||
+          subscription.status === "past_due";
 
-      try {
-        posthog?.capture({
-          distinctId: res.data.userId,
-          event: "subscription change",
-          properties: {
-            type: event.type,
-            $set: {
-              tier: isActive ? "pro" : "hobby",
+        // get the subscription price details
+        const lineItem = subscription.items.data[0];
+
+        // update/create the subscription in the database
+        const { price } = lineItem;
+
+        const res = subscriptionMetadataSchema.safeParse(subscription.metadata);
+
+        if (!res.success) {
+          return NextResponse.json(
+            { error: "Missing user ID" },
+            { status: 400 },
+          );
+        }
+
+        const subscriptionItem = subscription.items.data[0];
+        const interval = subscriptionItem.price.recurring?.interval;
+
+        if (!interval) {
+          throw new Error(
+            `Missing interval in subscription ${subscription.id}`,
+          );
+        }
+        // create or update the subscription in the database
+        await prisma.subscription.upsert({
+          where: {
+            id: subscription.id,
+          },
+          create: {
+            id: subscription.id,
+            active: isActive,
+            priceId: price.id,
+            currency: subscriptionItem.price.currency,
+            interval,
+            amount: subscriptionItem.price.unit_amount,
+            status: subscription.status,
+            createdAt: toDate(subscription.created),
+            periodStart: toDate(subscription.current_period_start),
+            periodEnd: toDate(subscription.current_period_end),
+          },
+          update: {
+            active: isActive,
+            priceId: price.id,
+            currency: subscriptionItem.price.currency,
+            interval,
+            amount: subscriptionItem.price.unit_amount,
+            status: subscription.status,
+            createdAt: toDate(subscription.created),
+            periodStart: toDate(subscription.current_period_start),
+            periodEnd: toDate(subscription.current_period_end),
+          },
+        });
+
+        // update the user with the subscription id
+        await prisma.user.update({
+          where: {
+            id: res.data.userId,
+          },
+          data: {
+            subscriptionId: subscription.id,
+          },
+        });
+
+        try {
+          posthog?.capture({
+            distinctId: res.data.userId,
+            event: "subscription change",
+            properties: {
+              type: event.type,
+              $set: {
+                tier: isActive ? "pro" : "hobby",
+              },
+            },
+          });
+        } catch (e) {
+          Sentry.captureException(e);
+        }
+
+        break;
+      }
+      case "checkout.session.expired": {
+        console.info("Checkout session expired");
+        const session = event.data.object as Stripe.Checkout.Session;
+        // When a Checkout Session expires, the customer's email isn't returned in
+        // the webhook payload unless they give consent for promotional content
+        const email = session.customer_details?.email;
+        const recoveryUrl = session.after_expiration?.recovery?.url;
+        const userId = session.metadata?.userId;
+        if (!userId) {
+          console.info("No user ID found in Checkout Session metadata");
+          Sentry.captureMessage(
+            "No user ID found in Checkout Session metadata",
+          );
+          break;
+        }
+        // Do nothing if the Checkout Session has no email or recovery URL
+        if (!email || !recoveryUrl) {
+          console.info("No email or recovery URL found in Checkout Session");
+          Sentry.captureMessage(
+            "No email or recovery URL found in Checkout Session",
+          );
+          break;
+        }
+        const promoEmailKey = `promo_email_sent:${email}`;
+        // Track that a promotional email opportunity has been shown to this user
+        const hasReceivedPromo = await kv.get(promoEmailKey);
+        console.info("Has received promo", hasReceivedPromo);
+
+        const user = await prisma.user.findUnique({
+          where: {
+            id: userId,
+          },
+          select: {
+            locale: true,
+            subscription: {
+              select: {
+                active: true,
+              },
             },
           },
         });
-      } catch (e) {
-        Sentry.captureException(e);
-      }
 
-      break;
-    }
-    case "checkout.session.expired": {
-      console.info("Checkout session expired");
-      const session = event.data.object as Stripe.Checkout.Session;
-      // When a Checkout Session expires, the customer's email isn't returned in
-      // the webhook payload unless they give consent for promotional content
-      const email = session.customer_details?.email;
-      const recoveryUrl = session.after_expiration?.recovery?.url;
-      const userId = session.metadata?.userId;
-      if (!userId) {
-        console.info("No user ID found in Checkout Session metadata");
-        Sentry.captureMessage("No user ID found in Checkout Session metadata");
+        const isPro = !!user?.subscription?.active;
+
+        // Avoid spamming people who abandon Checkout multiple times
+        if (user && !hasReceivedPromo && !isPro) {
+          console.info("Sending abandoned checkout email");
+          // Set the flag with a 30-day expiration (in seconds)
+          await kv.set(promoEmailKey, 1, { ex: 30 * 24 * 60 * 60, nx: true });
+          getEmailClient(user.locale ?? undefined).sendTemplate(
+            "AbandonedCheckoutEmail",
+            {
+              to: email,
+              from: {
+                name: "Luke from Rallly",
+                address: "luke@rallly.co",
+              },
+              props: {
+                name: session.customer_details?.name ?? undefined,
+                discount: 20,
+                couponCode: "GETPRO1Y20",
+                recoveryUrl,
+              },
+            },
+          );
+        }
+
         break;
       }
-      // Do nothing if the Checkout Session has no email or recovery URL
-      if (!email || !recoveryUrl) {
-        console.info("No email or recovery URL found in Checkout Session");
-        Sentry.captureMessage(
-          "No email or recovery URL found in Checkout Session",
+      default:
+        Sentry.captureException(
+          new Error(`Unhandled event type: ${event.type}`),
         );
-        break;
-      }
-      const promoEmailKey = `promo_email_sent:${email}`;
-      // Track that a promotional email opportunity has been shown to this user
-      const hasReceivedPromo = await kv.get(promoEmailKey);
-      console.info("Has received promo", hasReceivedPromo);
-
-      const user = await prisma.user.findUnique({
-        where: {
-          id: userId,
-        },
-        select: {
-          locale: true,
-          subscription: {
-            select: {
-              active: true,
-            },
-          },
-        },
-      });
-
-      const isPro = !!user?.subscription?.active;
-
-      // Avoid spamming people who abandon Checkout multiple times
-      if (user && !hasReceivedPromo && !isPro) {
-        console.info("Sending abandoned checkout email");
-        // Set the flag with a 30-day expiration (in seconds)
-        await kv.set(promoEmailKey, 1, { ex: 30 * 24 * 60 * 60, nx: true });
-        getEmailClient(user.locale ?? undefined).sendTemplate(
-          "AbandonedCheckoutEmail",
-          {
-            to: email,
-            from: {
-              name: "Luke from Rallly",
-              address: "luke@rallly.co",
-            },
-            props: {
-              name: session.customer_details?.name ?? undefined,
-              discount: 20,
-              couponCode: "GETPRO1Y20",
-              recoveryUrl,
-            },
-          },
+        // Unexpected event type
+        return NextResponse.json(
+          { error: "Unhandled event type" },
+          { status: 400 },
         );
-      }
-
-      break;
     }
-    default:
-      Sentry.captureException(new Error(`Unhandled event type: ${event.type}`));
-      // Unexpected event type
-      return NextResponse.json(
-        { error: "Unhandled event type" },
-        { status: 400 },
-      );
+  } catch (err) {
+    const error =
+      err instanceof Error ? err.message : "An unexpected error occurred";
+    Sentry.captureException(err);
+    return NextResponse.json({ error }, { status: 500 });
   }
 
   waitUntil(Promise.all([posthog?.shutdown()]));
diff --git a/packages/billing/package.json b/packages/billing/package.json
index 850f7b9d3..b53f62504 100644
--- a/packages/billing/package.json
+++ b/packages/billing/package.json
@@ -9,6 +9,7 @@
   "scripts": {
     "normalize-subscription-metadata": "dotenv -e ../../.env -- tsx ./src/scripts/normalize-metadata.ts",
     "checkout-expiry": "dotenv -e ../../.env -- tsx ./src/scripts/checkout-expiry.ts",
+    "subscription-data-sync": "dotenv -e ../../.env -- tsx ./src/scripts/subscription-data-sync.ts",
     "type-check": "tsc --pretty --noEmit",
     "lint": "eslint ./src"
   },
diff --git a/packages/billing/src/scripts/subscription-data-sync.ts b/packages/billing/src/scripts/subscription-data-sync.ts
new file mode 100644
index 000000000..521b70438
--- /dev/null
+++ b/packages/billing/src/scripts/subscription-data-sync.ts
@@ -0,0 +1,55 @@
+import { prisma } from "@rallly/database";
+
+import { stripe } from "../lib/stripe";
+
+(async function syncSubscriptionData() {
+  const BATCH_SIZE = 10;
+  let processed = 0;
+  let failed = 0;
+
+  const userSubscriptions = await prisma.subscription.findMany({
+    select: {
+      id: true,
+    },
+    take: BATCH_SIZE,
+  });
+
+  console.info(`🚀 Syncing ${userSubscriptions.length} subscriptions...`)
+
+  for (const userSubscription of userSubscriptions) {
+    try {
+      const subscription = await stripe.subscriptions.retrieve(
+        userSubscription.id,
+      );
+
+      const subscriptionItem = subscription.items.data[0];
+      const interval = subscriptionItem.price.recurring?.interval;
+
+      if (!interval) {
+        console.info(`🚨 Missing interval in subscription ${subscription.id}`);
+        +        failed++;
+        continue;
+      }
+
+      await prisma.subscription.update({
+        where: {
+          id: subscription.id,
+        },
+        data: {
+          amount: subscriptionItem.price.unit_amount,
+          currency: subscriptionItem.price.currency,
+          interval: subscriptionItem.price.recurring?.interval,
+          status: subscription.status,
+        },
+      });
+
+      console.info(`✅ Subscription ${subscription.id} synced`);
+      processed++;
+    } catch (error) {
+      console.error(`❌ Failed to sync subscription ${userSubscription.id}:`, error);
+      failed++;
+    }
+  }
+
+  console.info(`📊 Sync complete: ${processed} processed, ${failed} failed`);
+})();
\ No newline at end of file
diff --git a/packages/database/prisma/migrations/20250217082042_add_subscription_fields/migration.sql b/packages/database/prisma/migrations/20250217082042_add_subscription_fields/migration.sql
new file mode 100644
index 000000000..5be24cb7e
--- /dev/null
+++ b/packages/database/prisma/migrations/20250217082042_add_subscription_fields/migration.sql
@@ -0,0 +1,3 @@
+-- AlterTable
+ALTER TABLE "subscriptions" ADD COLUMN     "amount" INTEGER,
+ADD COLUMN     "status" TEXT;
diff --git a/packages/database/prisma/schema.prisma b/packages/database/prisma/schema.prisma
index 9595ac44d..6d112dc94 100644
--- a/packages/database/prisma/schema.prisma
+++ b/packages/database/prisma/schema.prisma
@@ -88,6 +88,8 @@ model UserPaymentData {
 model Subscription {
   id            String   @id
   priceId       String   @map("price_id")
+  amount        Int?
+  status        String?
   active        Boolean
   currency      String?
   interval      String?