Sync Autumn billing status to Loops and add billing backfill (#269)

drizzle/0023_sad_cobalt_man.sql

@@ -0,0 +1,14 @@
+ALTER TABLE `billing_customer_status` ADD `paid_plan_status` text;--> statement-breakpoint
+UPDATE `billing_customer_status`
+SET `paid_plan_status` = (
+  SELECT json_extract(subscription.value, '$.status')
+  FROM json_each(`billing_customer_status`.`customer_json`, '$.subscriptions') AS subscription
+  WHERE json_extract(subscription.value, '$.planId') = 'base-plan'
+  ORDER BY CASE
+    WHEN json_extract(subscription.value, '$.status') = 'active' THEN 0
+    ELSE 1
+  END
+  LIMIT 1
+)
+WHERE `paid_plan_status` IS NULL
+  AND json_valid(`customer_json`);

drizzle/meta/_journal.json

@@ -162,6 +162,13 @@
       "when": 1781107930529,
       "tag": "0022_purple_hitman",
       "breakpoints": true
+    },
+    {
+      "idx": 23,
+      "version": "6",
+      "when": 1781467831570,
+      "tag": "0023_sad_cobalt_man",
+      "breakpoints": true
     }
   ]
 }

src/db/billing.schema.ts

@@ -8,6 +8,7 @@ export const billingCustomerStatus = sqliteTable("billing_customer_status", {
     .references(() => organization.id, { onDelete: "cascade" }),
   isPaying: integer("is_paying", { mode: "boolean" }).notNull().default(false),
   paidPlanId: text("paid_plan_id"),
+  paidPlanStatus: text("paid_plan_status"),
   // Full Autumn customer payload — escape hatch for any field we don't flatten,
   // queryable via json_extract so we never have to widen this table.
   customerJson: text("customer_json").notNull(),

src/server/billing/customer-status-model.test.ts

@@ -13,6 +13,7 @@ describe("deriveBillingCustomerStatusSnapshot", () => {
       organizationId: "org_123",
       isPaying: true,
       paidPlanId: AUTUMN_PAID_PLAN_ID,
+      paidPlanStatus: "active",
     });
   });
 
@@ -39,6 +40,7 @@ describe("deriveBillingCustomerStatusSnapshot", () => {
 
     expect(snapshot.isPaying).toBe(false);
     expect(snapshot.paidPlanId).toBeNull();
+    expect(snapshot.paidPlanStatus).toBeNull();
   });
 
   it("records a scheduled (not-yet-active) paid plan as not paying", () => {
@@ -51,6 +53,7 @@ describe("deriveBillingCustomerStatusSnapshot", () => {
       organizationId: "org_456",
       isPaying: false,
       paidPlanId: AUTUMN_PAID_PLAN_ID,
+      paidPlanStatus: "scheduled",
     });
   });
 
@@ -65,5 +68,6 @@ describe("deriveBillingCustomerStatusSnapshot", () => {
 
     expect(snapshot.isPaying).toBe(true);
     expect(snapshot.paidPlanId).toBe(AUTUMN_PAID_PLAN_ID);
+    expect(snapshot.paidPlanStatus).toBe("active");
   });
 });

src/server/billing/customer-status-model.ts

@@ -18,6 +18,7 @@ export type BillingCustomerStatusSnapshot = {
   organizationId: string;
   isPaying: boolean;
   paidPlanId: string | null;
+  paidPlanStatus: string | null;
   customerJson: string;
   syncedAt: string;
 };
@@ -36,6 +37,7 @@ export function deriveBillingCustomerStatusSnapshot(
     organizationId,
     isPaying: subscription?.status === "active",
     paidPlanId: subscription?.planId ?? null,
+    paidPlanStatus: subscription?.status ?? null,
     // Full payload kept verbatim — query rarely-used fields via json_extract.
     customerJson: JSON.stringify(customer),
     syncedAt: new Date().toISOString(),

src/server/billing/customer-status-sync.ts

@@ -6,6 +6,7 @@ import {
   deriveBillingCustomerStatusSnapshot,
   type BillingCustomerStatusSnapshot,
 } from "./customer-status-model";
+import { syncBillingStatusToLoops } from "./loops-sync";
 
 export async function syncAutumnCustomerStatus(customerId: string) {
   // getOrCreate is effectively a "get" here — a billing.updated webhook always
@@ -13,6 +14,7 @@ export async function syncAutumnCustomerStatus(customerId: string) {
   const customer = await autumn.customers.getOrCreate({ customerId });
   const snapshot = deriveBillingCustomerStatusSnapshot(customer);
   await upsertBillingCustomerStatus(snapshot);
+  await syncBillingStatusToLoops(snapshot);
   return snapshot;
 }
 
@@ -27,6 +29,7 @@ async function upsertBillingCustomerStatus(
       set: {
         isPaying: snapshot.isPaying,
         paidPlanId: snapshot.paidPlanId,
+        paidPlanStatus: snapshot.paidPlanStatus,
         customerJson: snapshot.customerJson,
         syncedAt: snapshot.syncedAt,
         updatedAt: sql`(current_timestamp)`,

src/server/billing/loops-contact-properties.test.ts

@@ -0,0 +1,31 @@
+import { describe, expect, it } from "vitest";
+import {
+  getBillingLoopsContactProperties,
+  LOOPS_BILLING_PLAN_NONE,
+} from "./loops-contact-properties";
+
+describe("getBillingLoopsContactProperties", () => {
+  it("maps Autumn billing fields to Loops custom properties", () => {
+    expect(
+      getBillingLoopsContactProperties({
+        paidPlanId: "base-plan",
+        paidPlanStatus: "active",
+      }),
+    ).toEqual({
+      billingPlanId: "base-plan",
+      billingPlanStatus: "active",
+    });
+  });
+
+  it("uses explicit none values when the customer has no paid plan", () => {
+    expect(
+      getBillingLoopsContactProperties({
+        paidPlanId: null,
+        paidPlanStatus: null,
+      }),
+    ).toEqual({
+      billingPlanId: LOOPS_BILLING_PLAN_NONE,
+      billingPlanStatus: LOOPS_BILLING_PLAN_NONE,
+    });
+  });
+});

src/server/billing/loops-contact-properties.ts

@@ -0,0 +1,15 @@
+import type { BillingCustomerStatusSnapshot } from "./customer-status-model";
+
+export const LOOPS_BILLING_PLAN_NONE = "none";
+
+export function getBillingLoopsContactProperties(
+  snapshot: Pick<
+    BillingCustomerStatusSnapshot,
+    "paidPlanId" | "paidPlanStatus"
+  >,
+) {
+  return {
+    billingPlanId: snapshot.paidPlanId ?? LOOPS_BILLING_PLAN_NONE,
+    billingPlanStatus: snapshot.paidPlanStatus ?? LOOPS_BILLING_PLAN_NONE,
+  };
+}

src/server/billing/loops-sync.ts

@@ -0,0 +1,55 @@
+import { eq } from "drizzle-orm";
+import { db } from "@/db";
+import { member, user } from "@/db/schema";
+import {
+  getContactNameParts,
+  updateLoopsContact,
+} from "@/server/email/loops-client";
+import { getOptionalEnvValue } from "@/server/lib/runtime-env";
+import type { BillingCustomerStatusSnapshot } from "./customer-status-model";
+import { getBillingLoopsContactProperties } from "./loops-contact-properties";
+
+export async function syncBillingStatusToLoops(
+  snapshot: BillingCustomerStatusSnapshot,
+) {
+  const apiKey = await getOptionalEnvValue("LOOPS_API_KEY");
+
+  if (!apiKey) {
+    console.warn(
+      "Skipping Loops billing contact sync: LOOPS_API_KEY is not set",
+    );
+    return;
+  }
+
+  const contacts = await getOrganizationContacts(snapshot.organizationId);
+  const billingProperties = getBillingLoopsContactProperties(snapshot);
+
+  for (const contact of contacts) {
+    await updateLoopsContact({
+      apiKey,
+      payload: {
+        email: contact.email,
+        userId: contact.userId,
+        userGroup: "app-user",
+        ...getContactNameParts(contact.name),
+        ...billingProperties,
+      },
+      logContext: {
+        action: "billing-contact-sync",
+        organizationId: snapshot.organizationId,
+      },
+    });
+  }
+}
+
+async function getOrganizationContacts(organizationId: string) {
+  return db
+    .select({
+      userId: user.id,
+      email: user.email,
+      name: user.name,
+    })
+    .from(member)
+    .innerJoin(user, eq(member.userId, user.id))
+    .where(eq(member.organizationId, organizationId));
+}

src/server/email/loops-client.ts

@@ -0,0 +1,70 @@
+const LOOPS_CONTACT_UPDATE_URL = "https://app.loops.so/api/v1/contacts/update";
+
+type LoopsContactProperty =
+  | string
+  | number
+  | boolean
+  | null
+  | undefined
+  | Record<string, boolean>;
+
+type LoopsContactUpdatePayload = {
+  email?: string;
+  userId?: string;
+  firstName?: string;
+  lastName?: string;
+  source?: string;
+  subscribed?: boolean;
+  userGroup?: string;
+  mailingLists?: Record<string, boolean>;
+} & Record<string, LoopsContactProperty>;
+
+export async function updateLoopsContact({
+  apiKey,
+  payload,
+  logContext,
+}: {
+  apiKey: string;
+  payload: LoopsContactUpdatePayload;
+  logContext?: Record<string, unknown>;
+}) {
+  const response = await fetch(LOOPS_CONTACT_UPDATE_URL, {
+    method: "PUT",
+    headers: {
+      "Content-Type": "application/json",
+      Authorization: `Bearer ${apiKey}`,
+    },
+    body: JSON.stringify(payload),
+  });
+
+  if (response.ok) {
+    return;
+  }
+
+  const errorPayload = await response.json().catch(() => null);
+  console.error("Loops contact update error:", {
+    status: response.status,
+    email: payload.email,
+    userId: payload.userId,
+    ...logContext,
+    errorPayload,
+  });
+
+  throw new Error(`Failed to update Loops contact (${response.status})`);
+}
+
+export function getContactNameParts(name: string | null | undefined) {
+  const trimmedName = name?.trim();
+
+  if (!trimmedName) {
+    return {};
+  }
+
+  const [firstName, ...lastNameParts] = trimmedName.split(/\s+/);
+  const lastName = lastNameParts.join(" ");
+
+  return {
+    firstName,
+    ...(lastName ? { lastName } : {}),
+  };
+}

src/server/email/loops.ts

@@ -1,7 +1,10 @@
 import { env } from "cloudflare:workers";
+import {
+  getContactNameParts,
+  updateLoopsContact,
+} from "@/server/email/loops-client";
 
 const LOOPS_TRANSACTIONAL_URL = "https://app.loops.so/api/v1/transactional";
-const LOOPS_CONTACT_UPDATE_URL = "https://app.loops.so/api/v1/contacts/update";
 
 function getOptionalEnv(name: string) {
   const value: unknown = Reflect.get(env, name);
@@ -74,22 +77,6 @@ async function sendLoopsTransactionalEmail({
   );
 }
 
-function getContactNameParts(name: string | null | undefined) {
-  const trimmedName = name?.trim();
-
-  if (!trimmedName) {
-    return {};
-  }
-
-  const [firstName, ...lastNameParts] = trimmedName.split(/\s+/);
-  const lastName = lastNameParts.join(" ");
-
-  return {
-    firstName,
-    ...(lastName ? { lastName } : {}),
-  };
-}
-
 export async function upsertHostedSignupContact({
   userId,
   email,
@@ -108,34 +95,17 @@ export async function upsertHostedSignupContact({
     return;
   }
 
-  const response = await fetch(LOOPS_CONTACT_UPDATE_URL, {
-    method: "PUT",
-    headers: {
-      "Content-Type": "application/json",
-      Authorization: `Bearer ${apiKey}`,
-    },
-    body: JSON.stringify({
+  await updateLoopsContact({
+    apiKey,
+    payload: {
       email,
       userId,
       source: "openseo-signup",
       userGroup: "app-user",
       ...getContactNameParts(name),
-    }),
+    },
+    logContext: { action: "signup-contact-sync" },
   });
-
-  if (response.ok) {
-    return;
-  }
-
-  const errorPayload = await response.json().catch(() => null);
-  console.error("Loops signup contact sync error:", {
-    status: response.status,
-    email,
-    userId,
-    errorPayload,
-  });
-
-  throw new Error(`Failed to sync Loops signup contact (${response.status})`);
 }
 
 export async function sendHostedVerificationEmail({