From ced8e38fe8088ef7317c0fe1f80b7c448efe8380 Mon Sep 17 00:00:00 2001
From: Evan Jacobson <evanjacobson3@gmail.com>
Date: Tue, 5 May 2026 13:11:31 -0600
Subject: [PATCH] Adds a Subsciription Started email for credit-based billing

---
 apps/web/src/lib/kiloclaw/credit-billing.ts | 19 +++++--
 apps/web/src/lib/purchase-emails.test.ts    | 56 +++++++++++++++++++++
 2 files changed, 71 insertions(+), 4 deletions(-)

diff --git a/apps/web/src/lib/kiloclaw/credit-billing.ts b/apps/web/src/lib/kiloclaw/credit-billing.ts
index 680ff7508..2515dbf84 100644
--- a/apps/web/src/lib/kiloclaw/credit-billing.ts
+++ b/apps/web/src/lib/kiloclaw/credit-billing.ts
@@ -1167,6 +1167,8 @@ export async function enrollWithCredits(params: {
   const now = new Date();
   const periodMonths = plan === 'commit' ? 6 : 1;
   const periodEnd = addMonths(now, periodMonths);
+  const periodStartIso = now.toISOString();
+  const periodEndIso = periodEnd.toISOString();
   const periodKey = format(now, 'yyyy-MM');
   const categoryPrefix =
     plan === 'commit'
@@ -1229,8 +1231,6 @@ export async function enrollWithCredits(params: {
       .limit(1);
 
     // 5c: Upsert subscription row as pure credit
-    const nowIso = now.toISOString();
-    const periodEndIso = periodEnd.toISOString();
     const commitEndsAt = plan === 'commit' ? periodEndIso : null;
     const [mutatedSubscription] = await tx
       .insert(kiloclaw_subscriptions)
@@ -1240,7 +1240,7 @@ export async function enrollWithCredits(params: {
         payment_source: 'credits',
         status: 'active',
         plan,
-        current_period_start: nowIso,
+        current_period_start: periodStartIso,
         current_period_end: periodEndIso,
         credit_renewal_at: periodEndIso,
         stripe_subscription_id: null,
@@ -1259,7 +1259,7 @@ export async function enrollWithCredits(params: {
           payment_source: 'credits',
           status: 'active',
           plan,
-          current_period_start: nowIso,
+          current_period_start: periodStartIso,
           current_period_end: periodEndIso,
           credit_renewal_at: periodEndIso,
           stripe_subscription_id: null,
@@ -1355,6 +1355,17 @@ export async function enrollWithCredits(params: {
     await autoResumeIfSuspended(userId, instanceId);
   }
 
+  if (shouldSendSubscriptionStartedEmailForActivation(existingSub?.status ?? null)) {
+    await maybeSendKiloClawSubscriptionStartedEmail({
+      userId,
+      instanceId,
+      plan,
+      amountCents: Math.round(costMicrodollars / 10_000),
+      periodStart: periodStartIso,
+      periodEnd: periodEndIso,
+    });
+  }
+
   logInfo('Credit enrollment completed', {
     user_id: userId,
     instanceId,
diff --git a/apps/web/src/lib/purchase-emails.test.ts b/apps/web/src/lib/purchase-emails.test.ts
index 1507ef751..56aa6f1ed 100644
--- a/apps/web/src/lib/purchase-emails.test.ts
+++ b/apps/web/src/lib/purchase-emails.test.ts
@@ -1,3 +1,5 @@
+process.env.STRIPE_KILOCLAW_STANDARD_INTRO_PRICE_ID ||= 'price_standard_intro';
+
 import { eq, and } from 'drizzle-orm';
 import {
   kiloclaw_email_log,
@@ -272,6 +274,25 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => {
     return rows.length;
   }
 
+  async function seedCreditEnrollmentAnchor(userId: string) {
+    const [instance] = await db
+      .insert(kiloclaw_instances)
+      .values({
+        user_id: userId,
+        sandbox_id: `test-sandbox-${crypto.randomUUID()}`,
+      })
+      .returning();
+    await db.insert(kiloclaw_subscriptions).values({
+      user_id: userId,
+      instance_id: instance.id,
+      plan: 'trial',
+      status: 'trialing',
+      trial_started_at: new Date().toISOString(),
+      trial_ends_at: new Date(Date.now() + 7 * 86_400_000).toISOString(),
+    });
+    return instance;
+  }
+
   test('trialing trial → Stripe settlement sends one subscription-started email and writes the log row', async () => {
     const user = await insertTestUser({});
     const stripeSubscriptionId = `sub_trialing_${crypto.randomUUID()}`;
@@ -298,6 +319,41 @@ describe('applyStripeFundedKiloClawPeriod subscription-started email', () => {
     expect(await countEmailLogRows(user.id, instance.id)).toBe(1);
   });
 
+  test('trialing trial → credit enrollment sends one subscription-started email and writes the log row', async () => {
+    const user = await insertTestUser({ total_microdollars_acquired: 50_000_000 });
+    const instance = await seedCreditEnrollmentAnchor(user.id);
+
+    const mod = await import('@/lib/kiloclaw/credit-billing');
+    await mod.enrollWithCredits({
+      userId: user.id,
+      instanceId: instance.id,
+      plan: 'standard',
+      hadPaidSubscription: false,
+    });
+
+    expect(countSubscriptionStartedSends()).toBe(1);
+    expect(await countEmailLogRows(user.id, instance.id)).toBe(1);
+
+    const [subscription] = await db
+      .select()
+      .from(kiloclaw_subscriptions)
+      .where(eq(kiloclaw_subscriptions.instance_id, instance.id))
+      .limit(1);
+    const [emailLog] = await db
+      .select()
+      .from(kiloclaw_email_log)
+      .where(
+        and(
+          eq(kiloclaw_email_log.user_id, user.id),
+          eq(kiloclaw_email_log.instance_id, instance.id),
+          eq(kiloclaw_email_log.email_type, KILOCLAW_SUBSCRIPTION_STARTED_EMAIL_TYPE)
+        )
+      )
+      .limit(1);
+
+    expect(emailLog?.period_start).toBe(subscription.current_period_start);
+  });
+
   test('canceled trial → Stripe settlement sends one subscription-started email', async () => {
     const user = await insertTestUser({});
     const stripeSubscriptionId = `sub_canceled_trial_${crypto.randomUUID()}`;