feat: Cross-Context Awareness - Meeting info in email drafts

apps/web/utils/ai/reply/draft-with-knowledge.ts

@@ -38,6 +38,7 @@ const getUserPrompt = ({
   calendarAvailability,
   writingStyle,
   mcpContext,
+  meetingContext,
 }: {
   messages: (EmailForLLM & { to: string })[];
   emailAccount: EmailAccountWithAI;
@@ -47,6 +48,7 @@ const getUserPrompt = ({
   calendarAvailability: CalendarAvailabilityContext | null;
   writingStyle: string | null;
   mcpContext: string | null;
+  meetingContext: string | null;
 }) => {
   const userAbout = emailAccount.about
     ? `Context about the user:
@@ -137,13 +139,15 @@ You can suggest this booking link if it helps with scheduling (e.g., "Feel free
 
   const mcpToolsContext = mcpContext
     ? `Additional context fetched from external tools (such as CRM systems, task managers, or other integrations) that may help draft a response:
-    
+
 <external_tools_context>
 ${mcpContext}
 </external_tools_context>
 `
     : "";
 
+  const upcomingMeetingsContext = meetingContext || "";
+
   return `${userAbout}
 ${relevantKnowledge}
 ${historicalContext}
@@ -152,6 +156,7 @@ ${writingStylePrompt}
 ${calendarContext}
 ${bookingLinkContext}
 ${mcpToolsContext}
+${upcomingMeetingsContext}
 
 Here is the context of the email thread (from oldest to newest):
 ${getEmailListPrompt({ messages, messageMaxLength: 3000 })}
@@ -178,6 +183,7 @@ export async function aiDraftWithKnowledge({
   calendarAvailability,
   writingStyle,
   mcpContext,
+  meetingContext,
 }: {
   messages: (EmailForLLM & { to: string })[];
   emailAccount: EmailAccountWithAI;
@@ -187,6 +193,7 @@ export async function aiDraftWithKnowledge({
   calendarAvailability: CalendarAvailabilityContext | null;
   writingStyle: string | null;
   mcpContext: string | null;
+  meetingContext: string | null;
 }) {
   try {
     logger.info("Drafting email with knowledge base", {
@@ -211,6 +218,7 @@ export async function aiDraftWithKnowledge({
       calendarAvailability,
       writingStyle,
       mcpContext,
+      meetingContext,
     });
 
     const modelOptions = getModel(emailAccount.user);

apps/web/utils/email.test.ts

@@ -2,6 +2,7 @@ import { describe, it, expect } from "vitest";
 import {
   extractNameFromEmail,
   extractEmailAddress,
+  extractEmailAddresses,
   extractDomainFromEmail,
   participant,
   normalizeEmailAddress,
@@ -33,6 +34,124 @@ describe("email utils", () => {
     });
   });
 
+  describe("extractEmailAddresses", () => {
+    it("returns empty array for empty string", () => {
+      expect(extractEmailAddresses("")).toEqual([]);
+    });
+
+    it("extracts single email address", () => {
+      expect(extractEmailAddresses("john@example.com")).toEqual([
+        "john@example.com",
+      ]);
+    });
+
+    it("extracts multiple email addresses separated by commas", () => {
+      expect(
+        extractEmailAddresses("john@example.com, jane@example.com"),
+      ).toEqual(["john@example.com", "jane@example.com"]);
+    });
+
+    it("extracts emails from format 'Name <email>'", () => {
+      expect(extractEmailAddresses("John Doe <john@example.com>")).toEqual([
+        "john@example.com",
+      ]);
+    });
+
+    it("extracts multiple emails with names", () => {
+      expect(
+        extractEmailAddresses(
+          "John Doe <john@example.com>, Jane Smith <jane@example.com>",
+        ),
+      ).toEqual(["john@example.com", "jane@example.com"]);
+    });
+
+    it("handles mixed formats (with and without names)", () => {
+      expect(
+        extractEmailAddresses("John Doe <john@example.com>, jane@example.com"),
+      ).toEqual(["john@example.com", "jane@example.com"]);
+    });
+
+    it("handles commas inside quoted names", () => {
+      expect(
+        extractEmailAddresses(
+          '"Doe, John" <john@example.com>, jane@example.com',
+        ),
+      ).toEqual(["john@example.com", "jane@example.com"]);
+    });
+
+    it("trims whitespace around email addresses", () => {
+      expect(
+        extractEmailAddresses("  john@example.com  ,  jane@example.com  "),
+      ).toEqual(["john@example.com", "jane@example.com"]);
+    });
+
+    it("filters out invalid email addresses", () => {
+      expect(extractEmailAddresses("invalid-email, valid@example.com")).toEqual(
+        ["valid@example.com"],
+      );
+    });
+
+    it("handles multiple commas and extra spaces", () => {
+      expect(
+        extractEmailAddresses(
+          "john@example.com , jane@example.com , bob@example.com",
+        ),
+      ).toEqual(["john@example.com", "jane@example.com", "bob@example.com"]);
+    });
+
+    it("handles empty parts between commas", () => {
+      expect(
+        extractEmailAddresses("john@example.com,,jane@example.com"),
+      ).toEqual(["john@example.com", "jane@example.com"]);
+    });
+
+    it("handles trailing comma", () => {
+      expect(extractEmailAddresses("john@example.com,")).toEqual([
+        "john@example.com",
+      ]);
+    });
+
+    it("handles leading comma", () => {
+      expect(extractEmailAddresses(",john@example.com")).toEqual([
+        "john@example.com",
+      ]);
+    });
+
+    it("handles complex real-world header format", () => {
+      expect(
+        extractEmailAddresses(
+          '"Smith, John" <john.smith@example.com>, "Doe, Jane" <jane.doe@example.com>, admin@example.com',
+        ),
+      ).toEqual([
+        "john.smith@example.com",
+        "jane.doe@example.com",
+        "admin@example.com",
+      ]);
+    });
+
+    it("handles emails with plus addressing", () => {
+      expect(
+        extractEmailAddresses("user+tag@example.com, user+other@example.com"),
+      ).toEqual(["user+tag@example.com", "user+other@example.com"]);
+    });
+
+    it("handles emails with hyphens", () => {
+      expect(
+        extractEmailAddresses("no-reply@example.com, support-team@example.com"),
+      ).toEqual(["no-reply@example.com", "support-team@example.com"]);
+    });
+
+    it("handles single email with angle brackets", () => {
+      expect(extractEmailAddresses("<john@example.com>")).toEqual([
+        "john@example.com",
+      ]);
+    });
+
+    it("handles all invalid emails", () => {
+      expect(extractEmailAddresses("invalid, also-invalid")).toEqual([]);
+    });
+  });
+
   describe("extractEmailAddress", () => {
     it("extracts email from format 'Name <email>'", () => {
       expect(extractEmailAddress("John Doe <john.doe@gmail.com>")).toBe(

apps/web/utils/email.ts

@@ -15,6 +15,19 @@ export function extractNameFromEmail(email: string) {
   return email;
 }
 
+// Extracts all email addresses from a comma-separated header string
+// e.g., "John <john@example.com>, Jane <jane@example.com>" -> ["john@example.com", "jane@example.com"]
+export function extractEmailAddresses(header: string): string[] {
+  if (!header) return [];
+
+  // split by comma, but be careful about commas inside quoted names
+  const parts = header.split(/,(?=(?:[^"]*"[^"]*")*[^"]*$)/);
+
+  return parts
+    .map((part) => extractEmailAddress(part.trim()))
+    .filter((email) => email.length > 0);
+}
+
 // Converts "John Doe <john.doe@gmail>" to "john.doe@gmail"
 export function extractEmailAddress(email: string): string {
   if (!email) return "";