fix(webapp): remove deleted accounts from Loops marketing list (#3010)

When a user deletes their last organization, remove their contact from Loops
to prevent future marketing emails.

- Idempotent: safe to call multiple times
- Non-blocking: Loops failures do not block org deletion
- Conditional: only runs when user has no remaining organizations

Author: JosephDoUrden

apps/webapp/app/services/deleteOrganization.server.ts

@@ -3,6 +3,7 @@ import { PrismaClient } from "@trigger.dev/database";
 import { prisma } from "~/db.server";
 import { featuresForRequest } from "~/features.server";
 import { DeleteProjectService } from "./deleteProject.server";
+import { loopsClient } from "./loops.server";
 import { getCurrentPlan } from "./platform.v3.server";
 
 export class DeleteOrganizationService {
@@ -82,5 +83,27 @@ export class DeleteOrganizationService {
         deletedAt: new Date(),
       },
     });
+
+    // Unsubscribe user from Loops if this was their last organization
+    const otherOrgs = await this.#prismaClient.organization.count({
+      where: {
+        members: { some: { userId } },
+        deletedAt: null,
+        id: { not: organization.id },
+      },
+    });
+
+    if (otherOrgs === 0) {
+      // This was user's last org - delete from Loops
+      const user = await this.#prismaClient.user.findUnique({
+        where: { id: userId },
+        select: { email: true },
+      });
+
+      if (user) {
+        // Fire and forget - don't block deletion on Loops API
+        loopsClient?.deleteContact({ email: user.email });
+      }
+    }
   }
 }

apps/webapp/app/services/loops.server.ts

@@ -22,6 +22,35 @@ class LoopsClient {
     });
   }
 
+  async deleteContact({ email }: { email: string }): Promise<boolean> {
+    logger.info(`Loops deleting contact`, { email });
+
+    try {
+      const response = await fetch(
+        `https://app.loops.so/api/v1/contacts/${encodeURIComponent(email)}`,
+        {
+          method: "DELETE",
+          headers: { Authorization: `Bearer ${this.apiKey}` },
+        }
+      );
+
+      if (!response.ok) {
+        // 404 is okay - contact already deleted
+        if (response.status === 404) {
+          logger.info(`Loops contact already deleted`, { email });
+          return true;
+        }
+        logger.error(`Loops deleteContact bad status`, { status: response.status, email });
+        return false;
+      }
+
+      return true;
+    } catch (error) {
+      logger.error(`Loops deleteContact failed`, { error, email });
+      return false;
+    }
+  }
+
   async #sendEvent({
     email,
     userId,

apps/webapp/test/loopsClient.test.ts

@@ -0,0 +1,127 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
+
+// We need to test the LoopsClient class directly, so we'll create a test instance
+// rather than importing the singleton (which depends on env vars)
+
+class LoopsClient {
+  constructor(private readonly apiKey: string) {}
+
+  async deleteContact({ email }: { email: string }): Promise<boolean> {
+    try {
+      const response = await fetch(
+        `https://app.loops.so/api/v1/contacts/${encodeURIComponent(email)}`,
+        {
+          method: "DELETE",
+          headers: { Authorization: `Bearer ${this.apiKey}` },
+        }
+      );
+
+      if (!response.ok) {
+        // 404 is okay - contact already deleted
+        if (response.status === 404) {
+          return true;
+        }
+        return false;
+      }
+
+      return true;
+    } catch (error) {
+      return false;
+    }
+  }
+}
+
+describe("LoopsClient", () => {
+  const originalFetch = global.fetch;
+  let mockFetch: ReturnType<typeof vi.fn>;
+
+  beforeEach(() => {
+    mockFetch = vi.fn();
+    global.fetch = mockFetch;
+  });
+
+  afterEach(() => {
+    global.fetch = originalFetch;
+  });
+
+  describe("deleteContact", () => {
+    it("should return true on successful deletion (200)", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: true,
+        status: 200,
+      });
+
+      const client = new LoopsClient("test-api-key");
+      const result = await client.deleteContact({ email: "test@example.com" });
+
+      expect(result).toBe(true);
+      expect(mockFetch).toHaveBeenCalledWith(
+        "https://app.loops.so/api/v1/contacts/test%40example.com",
+        {
+          method: "DELETE",
+          headers: { Authorization: "Bearer test-api-key" },
+        }
+      );
+    });
+
+    it("should return true when contact already deleted (404)", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: false,
+        status: 404,
+      });
+
+      const client = new LoopsClient("test-api-key");
+      const result = await client.deleteContact({ email: "test@example.com" });
+
+      expect(result).toBe(true);
+    });
+
+    it("should return false on API error (500)", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: false,
+        status: 500,
+      });
+
+      const client = new LoopsClient("test-api-key");
+      const result = await client.deleteContact({ email: "test@example.com" });
+
+      expect(result).toBe(false);
+    });
+
+    it("should return false on unauthorized (401)", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: false,
+        status: 401,
+      });
+
+      const client = new LoopsClient("test-api-key");
+      const result = await client.deleteContact({ email: "test@example.com" });
+
+      expect(result).toBe(false);
+    });
+
+    it("should return false on network error", async () => {
+      mockFetch.mockRejectedValueOnce(new Error("Network error"));
+
+      const client = new LoopsClient("test-api-key");
+      const result = await client.deleteContact({ email: "test@example.com" });
+
+      expect(result).toBe(false);
+    });
+
+    it("should properly encode email addresses with special characters", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: true,
+        status: 200,
+      });
+
+      const client = new LoopsClient("test-api-key");
+      await client.deleteContact({ email: "test+alias@example.com" });
+
+      expect(mockFetch).toHaveBeenCalledWith(
+        "https://app.loops.so/api/v1/contacts/test%2Balias%40example.com",
+        expect.any(Object)
+      );
+    });
+  });
+});