assistant: fix CC/BCC recipients not being added to draft replies

.cursor/commands/address-pr-comments.md

@@ -1,5 +1,7 @@
 Resolve all active PR comments (conversation + code review). Use `gh` CLI.
 
+Important: don't use sandbox mode as the commands won't work in sandbox.
+
 ## Critical Rules
 
 1. **ALWAYS reply to the specific comment** - use replies API, not new PR comment

.cursor/commands/create-pr.md

@@ -1,5 +1,7 @@
 # Open a PR
 
+Important: don't use sandbox mode as the commands won't work in sandbox.
+
 ## Step 1: Check state (ONE command)
 
 ```bash

.cursor/commands/next-step.md

@@ -0,0 +1,2 @@
+Continue to the next step.
+

.cursor/commands/step-by-step.md

@@ -0,0 +1,7 @@
+# Step-by-Step Execution
+
+Execute **one step at a time**. After each step, stop and wait for my approval before continuing.
+
+After each step, show:
+- ✅ What was completed
+- ➡️ What's next

.cursor/rules/testing.mdc

@@ -7,6 +7,7 @@ alwaysApply: false
 
 ## Testing Framework
 - `vitest` is used for testing
+- Run tests using `pnpm test` (not `npx vitest`)
 - Tests are colocated next to the tested file
   - Example: `dir/format.ts` and `dir/format.test.ts`
 - AI tests are placed in the `__tests__` directory and are not run by default (they use a real LLM)

apps/web/utils/ai/actions.ts

@@ -159,6 +159,8 @@ const draft: ActionFunction<{
     to: args.to ?? undefined,
     subject: args.subject ?? undefined,
     content: args.content ?? "",
+    cc: args.cc ?? undefined,
+    bcc: args.bcc ?? undefined,
   };
 
   const result = await client.draftEmail(

apps/web/utils/email/google.ts

@@ -628,7 +628,13 @@ export class GmailProvider implements EmailProvider {
 
   async draftEmail(
     email: ParsedMessage,
-    args: { to?: string; subject?: string; content: string },
+    args: {
+      to?: string;
+      subject?: string;
+      content: string;
+      cc?: string;
+      bcc?: string;
+    },
     userEmail: string,
     executedRule?: { id: string; threadId: string; emailAccountId: string },
   ): Promise<{ draftId: string }> {

apps/web/utils/email/microsoft.ts

@@ -485,7 +485,13 @@ export class OutlookProvider implements EmailProvider {
 
   async draftEmail(
     email: ParsedMessage,
-    args: { to?: string; subject?: string; content: string },
+    args: {
+      to?: string;
+      subject?: string;
+      content: string;
+      cc?: string;
+      bcc?: string;
+    },
     userEmail: string,
     executedRule?: { id: string; threadId: string; emailAccountId: string },
   ): Promise<{ draftId: string }> {

apps/web/utils/email/reply-all.test.ts

@@ -1,5 +1,5 @@
 import { describe, it, expect } from "vitest";
-import { buildReplyAllRecipients, formatCcList } from "./reply-all";
+import { buildReplyAllRecipients, formatCcList, mergeAndDedupeRecipients } from "./reply-all";
 import type { ParsedMessageHeaders } from "@/utils/types";
 
 describe("buildReplyAllRecipients", () => {
@@ -408,3 +408,26 @@ describe("formatCcList", () => {
     expect(result).toBe("user@example.com");
   });
 });
+
+describe("mergeAndDedupeRecipients", () => {
+  it("should handle display names correctly", () => {
+    const existing = ["john@example.com"];
+    const manual = "John Doe <john@example.com>, jane@example.com";
+    const result = mergeAndDedupeRecipients(existing, manual);
+    expect(result).toEqual(["john@example.com", "jane@example.com"]);
+  });
+
+  it("should be case-insensitive", () => {
+    const existing = ["john@example.com"];
+    const manual = "JOHN@example.com";
+    const result = mergeAndDedupeRecipients(existing, manual);
+    expect(result).toEqual(["john@example.com"]);
+  });
+
+  it("should sanitize empty and invalid entries", () => {
+    const existing = ["john@example.com"];
+    const manual = " , , invalid-email, jane@example.com";
+    const result = mergeAndDedupeRecipients(existing, manual);
+    expect(result).toEqual(["john@example.com", "jane@example.com"]);
+  });
+});

apps/web/utils/email/reply-all.ts

@@ -29,28 +29,47 @@ export function buildReplyAllRecipients(
 
   // Build CC list for reply-all behavior
   const ccSet = new Set<string>();
+  const seenEmails = new Set<string>();
 
   // Add original CC recipients if they exist
   if (headers.cc) {
     const originalCcAddresses = headers.cc
       .split(",")
-      .map((addr) => extractEmailAddress(addr.trim()))
-      .filter((addr) => addr && addr !== replyTo && addr !== currentUser);
+      .map((addr) => ({
+        raw: addr.trim(),
+        email: extractEmailAddress(addr.trim()),
+      }))
+      .filter(
+        ({ email }) => email && email !== replyTo && email !== currentUser,
+      );
 
-    for (const addr of originalCcAddresses) {
-      ccSet.add(addr);
+    for (const { raw, email } of originalCcAddresses) {
+      const key = email.toLowerCase();
+      if (!seenEmails.has(key)) {
+        seenEmails.add(key);
+        ccSet.add(email);
+      }
     }
   }
 
   // Add original TO recipients to CC (excluding the reply-to address and current user)
   if (headers.to) {
     const originalToAddresses = headers.to
       .split(",")
-      .map((addr) => extractEmailAddress(addr.trim()))
-      .filter((addr) => addr && addr !== replyTo && addr !== currentUser);
+      .map((addr) => ({
+        raw: addr.trim(),
+        email: extractEmailAddress(addr.trim()),
+      }))
+      .filter(
+        ({ email }) => email && email !== replyTo && email !== currentUser,
+      );
 
-    for (const addr of originalToAddresses) {
-      ccSet.add(addr);
+    for (const { raw, email } of originalToAddresses) {
+      const key = email.toLowerCase();
+      if (!seenEmails.has(key)) {
+        seenEmails.add(key);
+        ccSet.add(email);
+      }
     }
   }
 
@@ -67,3 +86,35 @@ export function buildReplyAllRecipients(
 export function formatCcList(ccList: string[]): string | undefined {
   return ccList.length > 0 ? ccList.join(", ") : undefined;
 }
+
+/**
+ * Merges manual CC/BCC recipients with existing recipients,
+ * ensuring deduplication and sanitization.
+ */
+export function mergeAndDedupeRecipients(
+  existing: string[],
+  manual: string | undefined,
+): string[] {
+  const result = [...existing];
+  const seen = new Set(existing.map((e) => extractEmailAddress(e).toLowerCase()));
+
+  if (manual) {
+    const manualEntries = manual
+      .split(",")
+      .map((s) => s.trim())
+      .filter(Boolean);
+
+    for (const entry of manualEntries) {
+      const email = extractEmailAddress(entry);
+      if (email) {
+        const key = email.toLowerCase();
+        if (!seen.has(key)) {
+          seen.add(key);
+          result.push(entry);
+        }
+      }
+    }
+  }
+
+  return result;
+}

apps/web/utils/email/types.ts

@@ -104,7 +104,13 @@ export interface EmailProvider {
   removeThreadLabels(threadId: string, labelIds: string[]): Promise<void>;
   draftEmail(
     email: ParsedMessage,
-    args: { to?: string; subject?: string; content: string },
+    args: {
+      to?: string;
+      subject?: string;
+      content: string;
+      cc?: string;
+      bcc?: string;
+    },
     userEmail: string,
     executedRule?: { id: string; threadId: string; emailAccountId: string },
   ): Promise<{ draftId: string }>;

apps/web/utils/gmail/mail.ts

@@ -15,7 +15,11 @@ import { createReplyContent } from "@/utils/gmail/reply";
 import type { EmailForAction } from "@/utils/ai/types";
 import { createScopedLogger } from "@/utils/logger";
 import { withGmailRetry } from "@/utils/gmail/retry";
-import { buildReplyAllRecipients, formatCcList } from "@/utils/email/reply-all";
+import {
+  buildReplyAllRecipients,
+  formatCcList,
+  mergeAndDedupeRecipients,
+} from "@/utils/email/reply-all";
 import { formatReplySubject } from "@/utils/email/subject";
 import { ensureEmailSendingEnabled } from "@/utils/mail";
 
@@ -252,6 +256,8 @@ export async function draftEmail(
     to?: string;
     subject?: string;
     content: string;
+    cc?: string;
+    bcc?: string;
     attachments?: Attachment[];
   },
   userEmail: string,
@@ -267,9 +273,16 @@ export async function draftEmail(
     userEmail,
   );
 
+  // Merge CC from reply-all with CC from args
+  const ccList = mergeAndDedupeRecipients(recipients.cc, args.cc);
+
+  // Sanitize BCC
+  const bccList = mergeAndDedupeRecipients([], args.bcc);
+
   const raw = await createRawMailMessage({
     to: recipients.to,
-    cc: formatCcList(recipients.cc),
+    cc: formatCcList(ccList),
+    bcc: formatCcList(bccList),
     subject: args.subject || originalEmail.headers.subject,
     messageHtml: html,
     messageText: text,

apps/web/utils/outlook/mail.ts

@@ -6,7 +6,10 @@ import type { ParsedMessage } from "@/utils/types";
 import type { EmailForAction } from "@/utils/ai/types";
 import { createOutlookReplyContent } from "@/utils/outlook/reply";
 import { forwardEmailHtml, forwardEmailSubject } from "@/utils/gmail/forward";
-import { buildReplyAllRecipients } from "@/utils/email/reply-all";
+import {
+  buildReplyAllRecipients,
+  mergeAndDedupeRecipients,
+} from "@/utils/email/reply-all";
 import { formatReplySubject } from "@/utils/email/subject";
 import { withOutlookRetry } from "@/utils/outlook/retry";
 import { extractEmailAddress, extractNameFromEmail } from "@/utils/email";
@@ -189,6 +192,8 @@ export async function draftEmail(
     to?: string;
     subject?: string;
     content: string;
+    cc?: string;
+    bcc?: string;
     attachments?: Attachment[];
   },
   userEmail: string,
@@ -213,8 +218,20 @@ export async function draftEmail(
     },
   };
 
+  // Build CC list from reply-all and args
+  const ccAddresses = mergeAndDedupeRecipients(recipients.cc, args.cc);
+
   // Convert CC addresses to Outlook format
-  const ccRecipients = recipients.cc.map((addr) => ({
+  const ccRecipients = ccAddresses.map((addr) => ({
+    emailAddress: {
+      address: extractEmailAddress(addr),
+      name: extractNameFromEmail(addr),
+    },
+  }));
+
+  // Handle BCC if provided
+  const bccAddresses = mergeAndDedupeRecipients([], args.bcc);
+  const bccRecipients = bccAddresses.map((addr) => ({
     emailAddress: {
       address: extractEmailAddress(addr),
       name: extractNameFromEmail(addr),
@@ -264,6 +281,7 @@ export async function draftEmail(
         },
         toRecipients: [toRecipient],
         ...(ccRecipients.length > 0 ? { ccRecipients } : {}),
+        ...(bccRecipients.length > 0 ? { bccRecipients } : {}),
       }),
     logger,
   );