diff --git a/apps/api/src/api-v1/webhooks/stripe-webhook.ts b/apps/api/src/api-v1/webhooks/stripe-webhook.ts
index 42efd43f..f6449853 100644
--- a/apps/api/src/api-v1/webhooks/stripe-webhook.ts
+++ b/apps/api/src/api-v1/webhooks/stripe-webhook.ts
@@ -2,24 +2,33 @@ import type Stripe from 'stripe'
 import { assert, HttpError } from '@agentic/platform-core'
 
 import type { HonoApp } from '@/lib/types'
-import { and, db, eq, schema } from '@/db'
+import { and, db, eq, type RawConsumer, schema } from '@/db'
 import { setConsumerStripeSubscriptionStatus } from '@/lib/consumers/utils'
 import { env } from '@/lib/env'
 import { stripe } from '@/lib/external/stripe'
 
 const relevantStripeEvents = new Set<Stripe.Event.Type>([
+  // Stripe Checkout Sessions
   'checkout.session.completed',
-  'checkout.session.expired',
-  'checkout.session.async_payment_failed',
-  'checkout.session.async_payment_succeeded',
+
+  // TODO: Handle these events
+  // 'checkout.session.expired',
+  // 'checkout.session.async_payment_failed',
+  // 'checkout.session.async_payment_succeeded',
+
+  // Stripe Subscriptions
   'customer.subscription.created',
+
+  // TODO: Test these events which should be able to all use the same code path
   'customer.subscription.updated',
   'customer.subscription.paused',
   'customer.subscription.resumed',
-  'customer.subscription.deleted',
-  'customer.subscription.pending_update_applied',
-  'customer.subscription.pending_update_expired',
-  'customer.subscription.trial_will_end'
+  'customer.subscription.deleted'
+
+  // TODO: Handle these events
+  // 'customer.subscription.pending_update_applied',
+  // 'customer.subscription.pending_update_expired',
+  // 'customer.subscription.trial_will_end'
 ])
 
 export function registerV1StripeWebhook(app: HonoApp) {
@@ -65,63 +74,199 @@ export function registerV1StripeWebhook(app: HonoApp) {
 
     try {
       switch (event.type) {
+        case 'checkout.session.completed': {
+          const checkoutSession = event.data.object
+          const { subscription: subscriptionOrId } = checkoutSession
+          assert(subscriptionOrId, 400, 'missing subscription')
+          const { consumerId, plan, userId, projectId, deploymentId } =
+            checkoutSession.metadata ?? {}
+          assert(consumerId, 400, 'missing metadata.consumerId')
+          assert(plan !== undefined, 400, 'missing metadata.plan')
+
+          const subscriptionId =
+            typeof subscriptionOrId === 'string'
+              ? subscriptionOrId
+              : subscriptionOrId.id
+
+          const [subscription, consumer] = await Promise.all([
+            // Make sure we have the full subscription instead of just the id
+            typeof subscriptionOrId === 'string'
+              ? stripe.subscriptions.retrieve(subscriptionId)
+              : subscriptionOrId,
+
+            db.query.consumers.findFirst({
+              where: and(eq(schema.consumers.id, consumerId))
+            })
+          ])
+          assert(
+            subscription,
+            404,
+            `stripe subscription "${subscriptionId}" not found`
+          )
+          assert(consumer, 404, `consumer "${consumerId}" not found`)
+
+          // TODO: Treat this as a transaction...
+          await Promise.all([
+            // Ensure the underlying Stripe Subscription has all the necessary
+            // metadata
+            stripe.subscriptions.update(subscription.id, {
+              metadata: {
+                ...subscription.metadata,
+                ...checkoutSession.metadata
+              }
+            }),
+
+            // Sync our Consumer's state with the Stripe Subscription's state
+            syncConsumerWithStripeSubscription({
+              consumer,
+              subscription,
+              plan,
+              userId,
+              projectId,
+              deploymentId
+            })
+          ])
+          break
+        }
+
+        case 'customer.subscription.created': {
+          // Stripe Checkout-created subscriptions won't have the metadata
+          // necessary to identify the consumer, so ignore this event for now.
+          const subscription = event.data.object
+          const { consumerId, userId, projectId, deploymentId, plan } =
+            subscription.metadata
+
+          // TODO: This should be coming from Stripe Checkout, and a very flow
+          // follow-up webhook event should record the subscription and
+          // initialize the consumer, but it feels wrong to me to just be
+          // logging and ignore this event. In the future, if we support both
+          // Stripe Checkout and non-Stripe Checkout-based subscription flows,
+          // then this codepath should act very similarly to
+          // `customer.subscription.updated`.
+          if (
+            !consumerId ||
+            !userId ||
+            !projectId ||
+            !deploymentId ||
+            plan === undefined
+          ) {
+            break
+          }
+
+          // Intentional fallthrough
+        }
+
+        case 'customer.subscription.paused':
+        case 'customer.subscription.resumed':
+        case 'customer.subscription.deleted':
         case 'customer.subscription.updated': {
           // https://docs.stripe.com/billing/subscriptions/overview#subscription-statuses
           const subscription = event.data.object
-          const { userId, projectId } = subscription.metadata
-          assert(userId, 400, 'missing metadata userId')
-          assert(projectId, 400, 'missing metadata projectId')
+          const { consumerId, userId, projectId, deploymentId, plan } =
+            subscription.metadata
+          assert(consumerId, 'missing metadata.consumerId')
+          assert(plan !== undefined, 400, 'missing metadata.plan')
 
           logger.info('stripe webhook', event.type, {
+            consumerId,
             userId,
             projectId,
+            deploymentId,
+            plan,
             status: subscription.status
           })
 
           const consumer = await db.query.consumers.findFirst({
-            where: and(
-              eq(schema.consumers.userId, userId),
-              eq(schema.consumers.projectId, projectId)
-            ),
-            with: {
-              user: true,
-              project: true
-            }
+            where: eq(schema.consumers.id, consumerId)
           })
-          assert(consumer, 404, 'consumer not found')
-
-          if (consumer.stripeStatus !== subscription.status) {
-            consumer.stripeStatus = subscription.status
-            setConsumerStripeSubscriptionStatus(consumer)
-
-            // TODO: update plan
-            await db
-              .update(schema.consumers)
-              .set({
-                stripeStatus: consumer.stripeStatus,
-                isStripeSubscriptionActive: consumer.isStripeSubscriptionActive
-              })
-              .where(eq(schema.consumers.id, consumer.id))
-
-            // TODO: invoke provider webhooks
-            // event.data.customer = consumer.getPublicDocument()
-            // await invokeWebhooks(consumer.project, event)
-          }
+          assert(consumer, 404, `consumer "${consumerId}" not found`)
 
+          // Sync our Consumer's state with the Stripe Subscription's state
+          await syncConsumerWithStripeSubscription({
+            consumer,
+            subscription,
+            plan,
+            userId,
+            projectId,
+            deploymentId
+          })
           break
         }
 
         default:
-          throw new Error(`unexpected unhandled event "${event.type}"`)
+          logger.warn(
+            `unexpected unhandled event "${event.id}" type "${event.type}"`,
+            event.data?.object
+          )
       }
-    } catch (err) {
+    } catch (err: any) {
       throw new HttpError({
-        message: `error processing stripe webhook type "${event.type}"`,
-        cause: err,
-        statusCode: 500
+        message: `error processing stripe webhook event "${event.id}" type "${event.type}": ${err.message}`,
+        cause: err.cause ?? err,
+        statusCode: err.statusCode ?? err
       })
     }
 
     return ctx.json({ status: 'ok' })
   })
 }
+
+/**
+ * Sync our database Consumer's state with the Stripe Subscription's state.
+ *
+ * For anything billing-related, Stripe's resources is always considered the
+ * single source of truth. Our database's `Consumer` state should always be
+ * derived from the corresponding Stripe subscription.
+ */
+export async function syncConsumerWithStripeSubscription({
+  consumer,
+  subscription,
+  plan,
+  userId,
+  projectId,
+  deploymentId
+}: {
+  consumer: RawConsumer
+  subscription: Stripe.Subscription
+  plan: string | null | undefined
+  userId?: string
+  projectId?: string
+  deploymentId?: string
+}) {
+  // These extra checks aren't really necessary, but they're nice sanity checks
+  // to ensure metadata consistency with our consumer
+  assert(
+    consumer.userId === userId,
+    400,
+    `consumer "${consumer.id}" user "${consumer.userId}" does not match stripe checkout metadata user "${userId}"`
+  )
+  assert(
+    consumer.projectId === projectId,
+    400,
+    `consumer "${consumer.id}" project "${consumer.projectId}" does not match stripe checkout metadata project "${projectId}"`
+  )
+
+  if (
+    consumer._stripeSubscriptionId !== subscription.id ||
+    consumer.stripeStatus !== subscription.status ||
+    consumer.plan !== plan ||
+    consumer.deploymentId !== deploymentId
+  ) {
+    consumer._stripeSubscriptionId = subscription.id
+    consumer.stripeStatus = subscription.status
+    setConsumerStripeSubscriptionStatus(consumer)
+
+    if (deploymentId) {
+      consumer.deploymentId = deploymentId
+    }
+
+    await db
+      .update(schema.consumers)
+      .set(consumer)
+      .where(eq(schema.consumers.id, consumer.id))
+
+    // TODO: invoke provider webhooks
+    // event.data.customer = consumer.getPublicDocument()
+    // await invokeWebhooks(consumer.project, event)
+  }
+}
diff --git a/apps/api/src/lib/billing/create-stripe-checkout-session.ts b/apps/api/src/lib/billing/create-stripe-checkout-session.ts
index be1f15cf..b058d961 100644
--- a/apps/api/src/lib/billing/create-stripe-checkout-session.ts
+++ b/apps/api/src/lib/billing/create-stripe-checkout-session.ts
@@ -90,8 +90,9 @@ export async function createStripeCheckoutSession(
     // const updateParams: Stripe.SubscriptionUpdateParams = {
     //   collection_method: 'charge_automatically',
     //   metadata: {
-    //     userId: consumer.userId,
+    //     plan: plan ?? null,
     //     consumerId: consumer.id,
+    //     userId: consumer.userId,
     //     projectId: project.id,
     //     deploymentId: deployment.id
     //   }
@@ -282,8 +283,9 @@ export async function createStripeCheckoutSession(
       // TODO: consider custom_text
       // TODO: consider optional_items
       metadata: {
-        userId: consumer.userId,
+        plan: plan ?? null,
         consumerId: consumer.id,
+        userId: consumer.userId,
         projectId: project.id,
         deploymentId: deployment.id
       }
diff --git a/apps/api/src/lib/billing/upsert-stripe-subscription.ts b/apps/api/src/lib/billing/upsert-stripe-subscription.ts
index 1049b196..a9907335 100644
--- a/apps/api/src/lib/billing/upsert-stripe-subscription.ts
+++ b/apps/api/src/lib/billing/upsert-stripe-subscription.ts
@@ -96,6 +96,7 @@ export async function upsertStripeSubscription(
     const updateParams: Stripe.SubscriptionUpdateParams = {
       collection_method: 'charge_automatically',
       metadata: {
+        plan: plan ?? null,
         userId: consumer.userId,
         consumerId: consumer.id,
         projectId: project.id,
@@ -268,8 +269,9 @@ export async function upsertStripeSubscription(
       items,
       // collection_method: 'charge_automatically',
       metadata: {
-        userId: consumer.userId,
+        plan: plan ?? null,
         consumerId: consumer.id,
+        userId: consumer.userId,
         projectId: project.id,
         deploymentId: deployment.id
       }
diff --git a/package.json b/package.json
index d1769f0a..d49c9a55 100644
--- a/package.json
+++ b/package.json
@@ -51,7 +51,7 @@
   },
   "prettier": "@fisch0920/config/prettier",
   "simple-git-hooks": {
-    "pre-commit": "pnpx lint-staged"
+    "pre-commit": "pnpm lint-staged"
   },
   "lint-staged": {
     "*.{ts,tsx}": [