Digest improvements

apps/web/app/api/ai/digest/route.ts

@@ -167,7 +167,9 @@ export const POST = withError(
 
       logger.with({ emailAccountId, messageId: message.id });
 
-      const emailAccount = await getEmailAccountWithAi({ emailAccountId });
+      const emailAccount = await getEmailAccountWithAi({
+        emailAccountId,
+      });
       if (!emailAccount) {
         throw new Error("Email account not found");
       }
@@ -182,7 +184,7 @@ export const POST = withError(
         },
       });
 
-      if (!summary) {
+      if (!summary?.content) {
         logger.info("Skipping digest item because it is not worth summarizing");
         return new NextResponse("OK", { status: 200 });
       }

apps/web/app/api/resend/digest/route.ts

@@ -212,6 +212,17 @@ async function sendEmail({
       return acc;
     }, {} as Digest);
 
+    if (Object.keys(executedRulesByRule).length === 0) {
+      logger.info(
+        "No executed rules found, skipping digest email",
+        loggerOptions,
+      );
+      return {
+        success: true,
+        message: "No executed rules found, skipping digest email",
+      };
+    }
+
     const token = await createUnsubscribeToken({ emailAccountId });
 
     logger.info("Sending digest email", loggerOptions);
@@ -226,6 +237,7 @@ async function sendEmail({
         date: new Date(),
         ruleNames: Object.fromEntries(ruleNameMap),
         ...executedRulesByRule,
+        emailAccountId,
       },
     });
 

apps/web/utils/ai/digest/summarize-email-for-digest.test.ts

@@ -4,38 +4,61 @@ import { schema as DigestEmailSummarySchema } from "@/utils/ai/digest/summarize-
 import type { EmailAccountWithAI } from "@/utils/llms/types";
 import type { EmailForLLM } from "@/utils/types";
 
+// Type for the email account with name property as expected by the function
+type EmailAccountForDigest = EmailAccountWithAI & {
+  name: string | null;
+};
+
 // Run with: pnpm test-ai TEST
 
 vi.mock("server-only", () => ({}));
 
 const isAiTest = process.env.RUN_AI_TESTS === "true";
 
+// Helper functions for common test data
+function getEmailAccount(overrides = {}): EmailAccountForDigest {
+  return {
+    id: "email-account-id",
+    userId: "user1",
+    email: "user@test.com",
+    about: "Software engineer working on email automation",
+    name: "Test User",
+    account: {
+      provider: "gmail",
+    },
+    user: {
+      aiModel: "gpt-4",
+      aiProvider: "openai",
+      aiApiKey: process.env.OPENAI_API_KEY || null,
+    },
+    ...overrides,
+  };
+}
+
+function getTestEmail(overrides = {}): EmailForLLM {
+  return {
+    id: "email-id",
+    from: "sender@example.com",
+    to: "user@test.com",
+    subject: "Test Email",
+    content: "This is a test email content",
+    ...overrides,
+  };
+}
+
 describe.runIf(isAiTest)("aiSummarizeEmailForDigest", () => {
   beforeEach(() => {
     vi.clearAllMocks();
   });
 
-  test("summarizes email with structured data", async () => {
-    const emailAccount: EmailAccountWithAI = {
-      id: "email-account-id",
-      userId: "user1",
-      email: "user@test.com",
-      about: null,
-      user: {
-        aiModel: "gpt-4",
-        aiProvider: "openai",
-        aiApiKey: process.env.OPENAI_API_KEY || null,
-      },
-    };
-
-    const messageToSummarize: EmailForLLM = {
-      id: "email-id",
+  test("successfully summarizes email with order details", async () => {
+    const emailAccount = getEmailAccount();
+    const messageToSummarize = getTestEmail({
       from: "orders@example.com",
-      to: "user@test.com",
       subject: "Order Confirmation #12345",
       content:
         "Thank you for your order! Order #12345 has been confirmed. Date: 2024-03-20. Items: 3. Total: $99.99",
-    };
+    });
 
     const result = await aiSummarizeEmailForDigest({
       ruleName: "order",
@@ -46,37 +69,22 @@ describe.runIf(isAiTest)("aiSummarizeEmailForDigest", () => {
     console.debug("Generated content:\n", result);
 
     expect(result).toMatchObject({
-      type: "structured",
-      content: expect.arrayContaining([
-        expect.objectContaining({
-          label: expect.any(String),
-          value: expect.any(String),
-        }),
-      ]),
+      content: expect.any(String),
     });
+
+    // Verify the result matches the schema
+    const validationResult = DigestEmailSummarySchema.safeParse(result);
+    expect(validationResult.success).toBe(true);
   }, 15_000);
 
-  test("summarizes email with unstructured content", async () => {
-    const emailAccount: EmailAccountWithAI = {
-      id: "email-account-id",
-      userId: "user1",
-      email: "user@test.com",
-      about: null,
-      user: {
-        aiModel: "gpt-4",
-        aiProvider: "openai",
-        aiApiKey: process.env.OPENAI_API_KEY || null,
-      },
-    };
-
-    const messageToSummarize: EmailForLLM = {
-      id: "email-id",
+  test("successfully summarizes email with meeting notes", async () => {
+    const emailAccount = getEmailAccount();
+    const messageToSummarize = getTestEmail({
       from: "team@example.com",
-      to: "user@test.com",
       subject: "Weekly Team Meeting Notes",
       content:
         "Hi team, Here are the notes from our weekly meeting: 1. Project timeline updated - Phase 1 completion delayed by 1 week 2. New team member joining next week 3. Client presentation scheduled for Friday",
-    };
+    });
 
     const result = await aiSummarizeEmailForDigest({
       ruleName: "meeting",
@@ -87,31 +95,20 @@ describe.runIf(isAiTest)("aiSummarizeEmailForDigest", () => {
     console.debug("Generated content:\n", result);
 
     expect(result).toMatchObject({
-      type: "unstructured",
       content: expect.any(String),
     });
+
+    const validationResult = DigestEmailSummarySchema.safeParse(result);
+    expect(validationResult.success).toBe(true);
   }, 15_000);
 
-  test("handles empty email content", async () => {
-    const emailAccount: EmailAccountWithAI = {
-      id: "email-account-id",
-      userId: "user1",
-      email: "user@test.com",
-      about: null,
-      user: {
-        aiModel: "gpt-4",
-        aiProvider: "openai",
-        aiApiKey: process.env.OPENAI_API_KEY || null,
-      },
-    };
-
-    const messageToSummarize: EmailForLLM = {
-      id: "email-id",
+  test("handles empty email content gracefully", async () => {
+    const emailAccount = getEmailAccount();
+    const messageToSummarize = getTestEmail({
       from: "empty@example.com",
-      to: "user@test.com",
       subject: "Empty Email",
       content: "",
-    };
+    });
 
     const result = await aiSummarizeEmailForDigest({
       ruleName: "other",
@@ -121,25 +118,13 @@ describe.runIf(isAiTest)("aiSummarizeEmailForDigest", () => {
 
     console.debug("Generated content:\n", result);
 
-    // Empty emails should return unstructured content
     expect(result).toMatchObject({
-      type: "unstructured",
       content: expect.any(String),
     });
   }, 15_000);
 
-  test("handles null message", async () => {
-    const emailAccount: EmailAccountWithAI = {
-      id: "email-account-id",
-      userId: "user1",
-      email: "user@test.com",
-      about: null,
-      user: {
-        aiModel: "gpt-4",
-        aiProvider: "openai",
-        aiApiKey: process.env.OPENAI_API_KEY || null,
-      },
-    };
+  test("handles null message gracefully", async () => {
+    const emailAccount = getEmailAccount();
 
     const result = await aiSummarizeEmailForDigest({
       ruleName: "other",
@@ -150,38 +135,121 @@ describe.runIf(isAiTest)("aiSummarizeEmailForDigest", () => {
     expect(result).toBeNull();
   }, 15_000);
 
-  test("ensures consistent output format", async () => {
-    const emailAccount: EmailAccountWithAI = {
-      id: "email-account-id",
-      userId: "user1",
-      email: "user@test.com",
-      about: null,
-      user: {
-        aiModel: "gpt-4",
-        aiProvider: "openai",
-        aiApiKey: process.env.OPENAI_API_KEY || null,
-      },
-    };
-
-    const messageToSummarize: EmailForLLM = {
-      id: "email-id",
-      from: "invoice@example.com",
-      to: "user@test.com",
-      subject: "Invoice #INV-2024-001",
+  test("handles different user configurations", async () => {
+    const emailAccount = getEmailAccount({
+      about: "Marketing manager focused on customer engagement",
+      name: "Marketing User",
+    });
+
+    const messageToSummarize = getTestEmail({
+      from: "newsletter@company.com",
+      subject: "Weekly Marketing Update",
       content:
-        "Invoice #INV-2024-001\nAmount: $150.00\nDue Date: 2024-04-01\nStatus: Pending",
-    };
+        "This week's marketing metrics: Email open rate: 25%, Click-through rate: 3.2%, Conversion rate: 1.8%",
+    });
 
     const result = await aiSummarizeEmailForDigest({
-      ruleName: "invoice",
+      ruleName: "newsletter",
       emailAccount,
       messageToSummarize,
     });
 
     console.debug("Generated content:\n", result);
 
-    // Verify the result matches the schema
-    const validationResult = DigestEmailSummarySchema.safeParse(result);
-    expect(validationResult.success).toBe(true);
+    expect(result).toMatchObject({
+      content: expect.any(String),
+    });
+  }, 15_000);
+
+  test("handles various email categories correctly", async () => {
+    const emailAccount = getEmailAccount();
+    const categories = ["invoice", "receipt", "travel", "notification"];
+
+    for (const category of categories) {
+      const messageToSummarize = getTestEmail({
+        from: `${category}@example.com`,
+        subject: `Test ${category} email`,
+        content: `This is a test ${category} email with sample content`,
+      });
+
+      const result = await aiSummarizeEmailForDigest({
+        ruleName: category,
+        emailAccount,
+        messageToSummarize,
+      });
+
+      console.debug(`Generated content for ${category}:\n`, result);
+
+      expect(result).toMatchObject({
+        content: expect.any(String),
+      });
+    }
+  }, 30_000);
+
+  test("handles promotional emails appropriately", async () => {
+    const emailAccount = getEmailAccount();
+    const messageToSummarize = getTestEmail({
+      from: "promotions@store.com",
+      subject: "50% OFF Everything! Limited Time Only!",
+      content:
+        "Don't miss our biggest sale of the year! Everything is 50% off for the next 24 hours only!",
+    });
+
+    const result = await aiSummarizeEmailForDigest({
+      ruleName: "marketing",
+      emailAccount,
+      messageToSummarize,
+    });
+
+    console.debug("Generated content:\n", result);
+
+    expect(result).toMatchObject({
+      content: expect.any(String),
+    });
+  }, 15_000);
+
+  test("handles direct messages to user in second person", async () => {
+    const emailAccount = getEmailAccount();
+    const messageToSummarize = getTestEmail({
+      from: "hr@company.com",
+      subject: "Your Annual Review is Due",
+      content:
+        "Hi Test User, Your annual performance review is due by Friday. Please complete the self-assessment form and schedule a meeting with your manager.",
+    });
+
+    const result = await aiSummarizeEmailForDigest({
+      ruleName: "hr",
+      emailAccount,
+      messageToSummarize,
+    });
+
+    console.debug("Generated content:\n", result);
+
+    expect(result).toMatchObject({
+      content: expect.any(String),
+    });
+  }, 15_000);
+
+  test("handles edge case with very long email content", async () => {
+    const emailAccount = getEmailAccount();
+    const longContent = `${"This is a very long email content. ".repeat(100)}End of long content.`;
+
+    const messageToSummarize = getTestEmail({
+      from: "long@example.com",
+      subject: "Very Long Email",
+      content: longContent,
+    });
+
+    const result = await aiSummarizeEmailForDigest({
+      ruleName: "other",
+      emailAccount,
+      messageToSummarize,
+    });
+
+    console.debug("Generated content:\n", result);
+
+    expect(result).toMatchObject({
+      content: expect.any(String),
+    });
   }, 15_000);
 });