From 4ee7ae7d329c25b16b283f3b9dd53a4e217c7315 Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 11:27:18 -0500
Subject: [PATCH 1/7] feat: include email attachments in agent.generate and
 tool calls

Fetch attachment download URLs from Resend, append them to email text
so sandbox/tools can download files, and inject image parts into agent
messages so the LLM can visually process images.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 lib/chat/validateChatRequest.ts               |   2 +
 .../__tests__/formatAttachmentsText.test.ts   |  49 ++++++
 .../__tests__/generateEmailResponse.test.ts   | 165 ++++++++++++++++++
 .../__tests__/getEmailAttachments.test.ts     | 108 ++++++++++++
 .../__tests__/validateNewEmailMemory.test.ts  | 101 ++++++++++-
 lib/emails/inbound/formatAttachmentsText.ts   |  18 ++
 lib/emails/inbound/generateEmailResponse.ts   |  30 +++-
 lib/emails/inbound/getEmailAttachments.ts     |  30 ++++
 lib/emails/inbound/validateNewEmailMemory.ts  |   7 +-
 9 files changed, 500 insertions(+), 10 deletions(-)
 create mode 100644 lib/emails/inbound/__tests__/formatAttachmentsText.test.ts
 create mode 100644 lib/emails/inbound/__tests__/generateEmailResponse.test.ts
 create mode 100644 lib/emails/inbound/__tests__/getEmailAttachments.test.ts
 create mode 100644 lib/emails/inbound/formatAttachmentsText.ts
 create mode 100644 lib/emails/inbound/getEmailAttachments.ts

diff --git a/lib/chat/validateChatRequest.ts b/lib/chat/validateChatRequest.ts
index 92219e6d5..c2c516be3 100644
--- a/lib/chat/validateChatRequest.ts
+++ b/lib/chat/validateChatRequest.ts
@@ -11,6 +11,7 @@ import { getApiKeyDetails } from "@/lib/keys/getApiKeyDetails";
 import { validateOrganizationAccess } from "@/lib/organizations/validateOrganizationAccess";
 import { setupConversation } from "@/lib/chat/setupConversation";
 import { validateMessages } from "@/lib/chat/validateMessages";
+import type { EmailAttachment } from "@/lib/emails/inbound/getEmailAttachments";
 
 export const chatRequestSchema = z
   .object({
@@ -50,6 +51,7 @@ export type ChatRequestBody = BaseChatRequestBody & {
   accountId: string;
   orgId: string | null;
   authToken?: string;
+  attachments?: EmailAttachment[];
 };
 
 /**
diff --git a/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts b/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts
new file mode 100644
index 000000000..820a3247c
--- /dev/null
+++ b/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts
@@ -0,0 +1,49 @@
+import { describe, it, expect } from "vitest";
+import { formatAttachmentsText } from "../formatAttachmentsText";
+import type { EmailAttachment } from "../getEmailAttachments";
+
+describe("formatAttachmentsText", () => {
+  it("returns empty string for empty array", () => {
+    expect(formatAttachmentsText([])).toBe("");
+  });
+
+  it("formats a single attachment", () => {
+    const attachments: EmailAttachment[] = [
+      {
+        id: "att-1",
+        filename: "logo.svg",
+        contentType: "image/svg+xml",
+        downloadUrl: "https://resend.com/dl/att-1",
+      },
+    ];
+
+    const result = formatAttachmentsText(attachments);
+
+    expect(result).toBe(
+      "\n\nAttached files:\n- logo.svg (image/svg+xml): https://resend.com/dl/att-1",
+    );
+  });
+
+  it("formats multiple attachments", () => {
+    const attachments: EmailAttachment[] = [
+      {
+        id: "att-1",
+        filename: "logo.svg",
+        contentType: "image/svg+xml",
+        downloadUrl: "https://resend.com/dl/att-1",
+      },
+      {
+        id: "att-2",
+        filename: "report.pdf",
+        contentType: "application/pdf",
+        downloadUrl: "https://resend.com/dl/att-2",
+      },
+    ];
+
+    const result = formatAttachmentsText(attachments);
+
+    expect(result).toContain("Attached files:");
+    expect(result).toContain("- logo.svg (image/svg+xml): https://resend.com/dl/att-1");
+    expect(result).toContain("- report.pdf (application/pdf): https://resend.com/dl/att-2");
+  });
+});
diff --git a/lib/emails/inbound/__tests__/generateEmailResponse.test.ts b/lib/emails/inbound/__tests__/generateEmailResponse.test.ts
new file mode 100644
index 000000000..ed5216ddd
--- /dev/null
+++ b/lib/emails/inbound/__tests__/generateEmailResponse.test.ts
@@ -0,0 +1,165 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { generateEmailResponse } from "../generateEmailResponse";
+import type { ChatRequestBody } from "@/lib/chat/validateChatRequest";
+
+import getGeneralAgent from "@/lib/agents/generalAgent/getGeneralAgent";
+import { getEmailRoomMessages } from "@/lib/emails/inbound/getEmailRoomMessages";
+
+vi.mock("@/lib/agents/generalAgent/getGeneralAgent", () => ({
+  default: vi.fn(),
+}));
+
+vi.mock("@/lib/emails/inbound/getEmailRoomMessages", () => ({
+  getEmailRoomMessages: vi.fn(),
+}));
+
+vi.mock("@/lib/emails/getEmailFooter", () => ({
+  getEmailFooter: vi.fn(() => "<footer>footer</footer>"),
+}));
+
+vi.mock("@/lib/supabase/rooms/selectRoomWithArtist", () => ({
+  selectRoomWithArtist: vi.fn(() => ({ artist_name: "Test Artist" })),
+}));
+
+const mockGenerate = vi.fn();
+
+describe("generateEmailResponse", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+
+    vi.mocked(getGeneralAgent).mockResolvedValue({
+      agent: { generate: mockGenerate },
+    } as unknown as Awaited<ReturnType<typeof getGeneralAgent>>);
+
+    mockGenerate.mockResolvedValue({ text: "Hello from assistant" });
+  });
+
+  it("throws when roomId is missing", async () => {
+    const body = { accountId: "acc-1", orgId: null, messages: [] } as ChatRequestBody;
+
+    await expect(generateEmailResponse(body)).rejects.toThrow(
+      "roomId is required to generate email response HTML",
+    );
+  });
+
+  it("generates response without attachments", async () => {
+    vi.mocked(getEmailRoomMessages).mockResolvedValue([{ role: "user", content: "Hi there" }]);
+
+    const body: ChatRequestBody = {
+      accountId: "acc-1",
+      orgId: null,
+      messages: [],
+      roomId: "room-1",
+    };
+
+    const result = await generateEmailResponse(body);
+
+    expect(mockGenerate).toHaveBeenCalledWith({
+      messages: [{ role: "user", content: "Hi there" }],
+    });
+    expect(result.text).toBe("Hello from assistant");
+    expect(result.html).toContain("Hello from assistant");
+    expect(result.html).toContain("<footer>footer</footer>");
+  });
+
+  it("appends image parts to last user message when image attachments exist", async () => {
+    vi.mocked(getEmailRoomMessages).mockResolvedValue([
+      { role: "user", content: "Check this image" },
+    ]);
+
+    const body: ChatRequestBody = {
+      accountId: "acc-1",
+      orgId: null,
+      messages: [],
+      roomId: "room-1",
+      attachments: [
+        {
+          id: "att-1",
+          filename: "logo.png",
+          contentType: "image/png",
+          downloadUrl: "https://resend.com/dl/att-1",
+        },
+      ],
+    };
+
+    await generateEmailResponse(body);
+
+    const callArgs = mockGenerate.mock.calls[0][0];
+    const lastUserMsg = callArgs.messages[0];
+
+    // Should have been converted to parts array with text + image
+    expect(Array.isArray(lastUserMsg.content)).toBe(true);
+    expect(lastUserMsg.content[0]).toEqual({ type: "text", text: "Check this image" });
+    expect(lastUserMsg.content[1]).toMatchObject({
+      type: "image",
+      mimeType: "image/png",
+    });
+    expect(lastUserMsg.content[1].image).toBeInstanceOf(URL);
+    expect(lastUserMsg.content[1].image.href).toBe("https://resend.com/dl/att-1");
+  });
+
+  it("does not modify messages when only non-image attachments exist", async () => {
+    vi.mocked(getEmailRoomMessages).mockResolvedValue([
+      { role: "user", content: "Check this file" },
+    ]);
+
+    const body: ChatRequestBody = {
+      accountId: "acc-1",
+      orgId: null,
+      messages: [],
+      roomId: "room-1",
+      attachments: [
+        {
+          id: "att-1",
+          filename: "report.pdf",
+          contentType: "application/pdf",
+          downloadUrl: "https://resend.com/dl/att-1",
+        },
+      ],
+    };
+
+    await generateEmailResponse(body);
+
+    const callArgs = mockGenerate.mock.calls[0][0];
+    const lastUserMsg = callArgs.messages[0];
+
+    // Should remain as plain string (no image parts to add)
+    expect(lastUserMsg.content).toBe("Check this file");
+  });
+
+  it("appends image parts to the last user message in multi-message conversations", async () => {
+    vi.mocked(getEmailRoomMessages).mockResolvedValue([
+      { role: "user", content: "First message" },
+      { role: "assistant", content: "Reply" },
+      { role: "user", content: "Here is the image" },
+    ]);
+
+    const body: ChatRequestBody = {
+      accountId: "acc-1",
+      orgId: null,
+      messages: [],
+      roomId: "room-1",
+      attachments: [
+        {
+          id: "att-1",
+          filename: "photo.jpg",
+          contentType: "image/jpeg",
+          downloadUrl: "https://resend.com/dl/att-1",
+        },
+      ],
+    };
+
+    await generateEmailResponse(body);
+
+    const callArgs = mockGenerate.mock.calls[0][0];
+    // First user message should be unchanged
+    expect(callArgs.messages[0].content).toBe("First message");
+    // Last user message should have image parts
+    expect(Array.isArray(callArgs.messages[2].content)).toBe(true);
+    expect(callArgs.messages[2].content[0]).toEqual({
+      type: "text",
+      text: "Here is the image",
+    });
+    expect(callArgs.messages[2].content[1].type).toBe("image");
+  });
+});
diff --git a/lib/emails/inbound/__tests__/getEmailAttachments.test.ts b/lib/emails/inbound/__tests__/getEmailAttachments.test.ts
new file mode 100644
index 000000000..537b4dfce
--- /dev/null
+++ b/lib/emails/inbound/__tests__/getEmailAttachments.test.ts
@@ -0,0 +1,108 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { getEmailAttachments } from "../getEmailAttachments";
+
+import { getResendClient } from "@/lib/emails/client";
+
+vi.mock("@/lib/emails/client", () => ({
+  getResendClient: vi.fn(),
+}));
+
+const mockList = vi.fn();
+
+describe("getEmailAttachments", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    vi.mocked(getResendClient).mockReturnValue({
+      emails: {
+        receiving: {
+          attachments: {
+            list: mockList,
+          },
+        },
+      },
+    } as ReturnType<typeof getResendClient>);
+  });
+
+  it("returns mapped attachments when Resend returns data", async () => {
+    mockList.mockResolvedValue({
+      data: {
+        data: [
+          {
+            id: "att-1",
+            filename: "logo.svg",
+            content_type: "image/svg+xml",
+            download_url: "https://resend.com/dl/att-1",
+            size: 1024,
+            content_disposition: "attachment",
+            expires_at: "2025-01-01T01:00:00Z",
+          },
+          {
+            id: "att-2",
+            filename: "report.pdf",
+            content_type: "application/pdf",
+            download_url: "https://resend.com/dl/att-2",
+            size: 2048,
+            content_disposition: "attachment",
+            expires_at: "2025-01-01T01:00:00Z",
+          },
+        ],
+      },
+    });
+
+    const result = await getEmailAttachments("email-123");
+
+    expect(mockList).toHaveBeenCalledWith({ emailId: "email-123" });
+    expect(result).toEqual([
+      {
+        id: "att-1",
+        filename: "logo.svg",
+        contentType: "image/svg+xml",
+        downloadUrl: "https://resend.com/dl/att-1",
+      },
+      {
+        id: "att-2",
+        filename: "report.pdf",
+        contentType: "application/pdf",
+        downloadUrl: "https://resend.com/dl/att-2",
+      },
+    ]);
+  });
+
+  it("returns empty array when no attachments exist", async () => {
+    mockList.mockResolvedValue({ data: { data: [] } });
+
+    const result = await getEmailAttachments("email-123");
+
+    expect(result).toEqual([]);
+  });
+
+  it("returns empty array when data is null", async () => {
+    mockList.mockResolvedValue({ data: null });
+
+    const result = await getEmailAttachments("email-123");
+
+    expect(result).toEqual([]);
+  });
+
+  it("defaults filename to 'attachment' when not provided", async () => {
+    mockList.mockResolvedValue({
+      data: {
+        data: [
+          {
+            id: "att-3",
+            filename: undefined,
+            content_type: "application/octet-stream",
+            download_url: "https://resend.com/dl/att-3",
+            size: 512,
+            content_disposition: "attachment",
+            expires_at: "2025-01-01T01:00:00Z",
+          },
+        ],
+      },
+    });
+
+    const result = await getEmailAttachments("email-123");
+
+    expect(result[0].filename).toBe("attachment");
+  });
+});
diff --git a/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts b/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
index 911e3221d..663ad8ecc 100644
--- a/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
+++ b/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
@@ -3,6 +3,13 @@ import { validateNewEmailMemory } from "../validateNewEmailMemory";
 import type { ResendEmailReceivedEvent } from "@/lib/emails/validateInboundEmailEvent";
 import { NextResponse } from "next/server";
 
+import selectAccountEmails from "@/lib/supabase/account_emails/selectAccountEmails";
+import { getEmailContent } from "@/lib/emails/inbound/getEmailContent";
+import { getEmailRoomId } from "@/lib/emails/inbound/getEmailRoomId";
+import { setupConversation } from "@/lib/chat/setupConversation";
+import { getEmailAttachments } from "@/lib/emails/inbound/getEmailAttachments";
+import { formatAttachmentsText } from "@/lib/emails/inbound/formatAttachmentsText";
+
 vi.mock("@/lib/supabase/account_emails/selectAccountEmails", () => ({
   default: vi.fn(),
 }));
@@ -35,17 +42,26 @@ vi.mock("@/lib/const", () => ({
   RECOUP_API_KEY: "test-recoup-api-key",
 }));
 
-import selectAccountEmails from "@/lib/supabase/account_emails/selectAccountEmails";
-import { getEmailContent } from "@/lib/emails/inbound/getEmailContent";
-import { getEmailRoomId } from "@/lib/emails/inbound/getEmailRoomId";
-import { setupConversation } from "@/lib/chat/setupConversation";
+vi.mock("@/lib/emails/inbound/getEmailAttachments", () => ({
+  getEmailAttachments: vi.fn(),
+}));
+
+vi.mock("@/lib/emails/inbound/formatAttachmentsText", () => ({
+  formatAttachmentsText: vi.fn(),
+}));
 
 const MOCK_ACCOUNT_ID = "aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee";
 const MOCK_ROOM_ID = "11111111-2222-3333-4444-555555555555";
 const MOCK_EMAIL_ID = "email-123";
 const MOCK_MESSAGE_ID = "msg-456";
 
-function createMockEvent(overrides?: Partial<ResendEmailReceivedEvent["data"]>): ResendEmailReceivedEvent {
+/**
+ *
+ * @param overrides
+ */
+function createMockEvent(
+  overrides?: Partial<ResendEmailReceivedEvent["data"]>,
+): ResendEmailReceivedEvent {
   return {
     type: "email.received",
     created_at: "2024-01-01T00:00:00.000Z",
@@ -77,6 +93,10 @@ describe("validateNewEmailMemory", () => {
     vi.mocked(getEmailRoomId).mockResolvedValue(undefined);
 
     vi.mocked(setupConversation).mockResolvedValue({ roomId: MOCK_ROOM_ID });
+
+    vi.mocked(getEmailAttachments).mockResolvedValue([]);
+
+    vi.mocked(formatAttachmentsText).mockReturnValue("");
   });
 
   it("includes authToken from RECOUP_API_KEY in chatRequestBody", async () => {
@@ -87,7 +107,10 @@ describe("validateNewEmailMemory", () => {
     // Should not be a response (duplicate)
     expect(result).not.toHaveProperty("response");
 
-    const { chatRequestBody } = result as { chatRequestBody: { authToken?: string }; emailText: string };
+    const { chatRequestBody } = result as {
+      chatRequestBody: { authToken?: string };
+      emailText: string;
+    };
     expect(chatRequestBody.authToken).toBe("test-recoup-api-key");
   });
 
@@ -95,7 +118,10 @@ describe("validateNewEmailMemory", () => {
     const event = createMockEvent();
 
     const result = await validateNewEmailMemory(event);
-    const { chatRequestBody } = result as { chatRequestBody: Record<string, unknown>; emailText: string };
+    const { chatRequestBody } = result as {
+      chatRequestBody: Record<string, unknown>;
+      emailText: string;
+    };
 
     expect(chatRequestBody.accountId).toBe(MOCK_ACCOUNT_ID);
     expect(chatRequestBody.orgId).toBeNull();
@@ -113,4 +139,65 @@ describe("validateNewEmailMemory", () => {
     const { response } = result as { response: NextResponse };
     expect(response.status).toBe(200);
   });
+
+  it("fetches attachments and includes them in chatRequestBody", async () => {
+    const mockAttachments = [
+      {
+        id: "att-1",
+        filename: "logo.svg",
+        contentType: "image/svg+xml",
+        downloadUrl: "https://resend.com/dl/att-1",
+      },
+    ];
+    vi.mocked(getEmailAttachments).mockResolvedValue(mockAttachments);
+    vi.mocked(formatAttachmentsText).mockReturnValue(
+      "\n\nAttached files:\n- logo.svg (image/svg+xml): https://resend.com/dl/att-1",
+    );
+
+    const event = createMockEvent();
+    const result = await validateNewEmailMemory(event);
+
+    expect(result).not.toHaveProperty("response");
+    const { chatRequestBody } = result as {
+      chatRequestBody: Record<string, unknown>;
+      emailText: string;
+    };
+    expect(chatRequestBody.attachments).toEqual(mockAttachments);
+    expect(getEmailAttachments).toHaveBeenCalledWith(MOCK_EMAIL_ID);
+  });
+
+  it("appends attachment URLs to emailText", async () => {
+    const attachmentText =
+      "\n\nAttached files:\n- logo.svg (image/svg+xml): https://resend.com/dl/att-1";
+    vi.mocked(getEmailAttachments).mockResolvedValue([
+      {
+        id: "att-1",
+        filename: "logo.svg",
+        contentType: "image/svg+xml",
+        downloadUrl: "https://resend.com/dl/att-1",
+      },
+    ]);
+    vi.mocked(formatAttachmentsText).mockReturnValue(attachmentText);
+
+    const event = createMockEvent();
+    const result = await validateNewEmailMemory(event);
+
+    const { emailText } = result as { chatRequestBody: Record<string, unknown>; emailText: string };
+    expect(emailText).toContain("Attached files:");
+    expect(emailText).toContain("https://resend.com/dl/att-1");
+  });
+
+  it("includes empty attachments array when no attachments exist", async () => {
+    vi.mocked(getEmailAttachments).mockResolvedValue([]);
+    vi.mocked(formatAttachmentsText).mockReturnValue("");
+
+    const event = createMockEvent();
+    const result = await validateNewEmailMemory(event);
+
+    const { chatRequestBody } = result as {
+      chatRequestBody: Record<string, unknown>;
+      emailText: string;
+    };
+    expect(chatRequestBody.attachments).toEqual([]);
+  });
 });
diff --git a/lib/emails/inbound/formatAttachmentsText.ts b/lib/emails/inbound/formatAttachmentsText.ts
new file mode 100644
index 000000000..9674fcb06
--- /dev/null
+++ b/lib/emails/inbound/formatAttachmentsText.ts
@@ -0,0 +1,18 @@
+import type { EmailAttachment } from "./getEmailAttachments";
+
+/**
+ * Formats attachment info as text to append to the email body.
+ * This makes download URLs available to the LLM and any tools
+ * (sandbox, legacy tools, etc.) via the prompt text.
+ *
+ * @param attachments - Array of email attachments with download URLs
+ * @returns Formatted text block listing attachments, or empty string if none
+ */
+export function formatAttachmentsText(attachments: EmailAttachment[]): string {
+  if (!attachments.length) return "";
+
+  const lines = attachments.map(
+    att => `- ${att.filename} (${att.contentType}): ${att.downloadUrl}`,
+  );
+  return `\n\nAttached files:\n${lines.join("\n")}`;
+}
diff --git a/lib/emails/inbound/generateEmailResponse.ts b/lib/emails/inbound/generateEmailResponse.ts
index 59edf811c..1c9c318f3 100644
--- a/lib/emails/inbound/generateEmailResponse.ts
+++ b/lib/emails/inbound/generateEmailResponse.ts
@@ -1,3 +1,4 @@
+import type { ModelMessage } from "ai";
 import { marked } from "marked";
 import { ChatRequestBody } from "@/lib/chat/validateChatRequest";
 import getGeneralAgent from "@/lib/agents/generalAgent/getGeneralAgent";
@@ -8,6 +9,7 @@ import { selectRoomWithArtist } from "@/lib/supabase/rooms/selectRoomWithArtist"
 /**
  * Generates the assistant response HTML for an email, including:
  * - Running the general agent to generate a reply for the given room
+ * - Appending image attachments as visual content parts to the last user message
  * - Fetching the room messages
  * - Appending a standardized footer with reply and link instructions
  *
@@ -17,7 +19,7 @@ import { selectRoomWithArtist } from "@/lib/supabase/rooms/selectRoomWithArtist"
 export async function generateEmailResponse(
   body: ChatRequestBody,
 ): Promise<{ text: string; html: string }> {
-  const { roomId } = body;
+  const { roomId, attachments } = body;
   if (!roomId) {
     throw new Error("roomId is required to generate email response HTML");
   }
@@ -25,7 +27,31 @@ export async function generateEmailResponse(
   const decision = await getGeneralAgent(body);
   const agent = decision.agent;
 
-  const messages = await getEmailRoomMessages(roomId);
+  const messages: ModelMessage[] = await getEmailRoomMessages(roomId);
+
+  // Append image attachments as visual content parts to the last user message
+  // so the LLM can visually process images (in addition to having download URLs in text)
+  if (attachments?.length) {
+    const imageAttachments = attachments.filter(a => a.contentType.startsWith("image/"));
+    if (imageAttachments.length) {
+      const lastUserIdx = messages.findLastIndex(m => m.role === "user");
+      if (lastUserIdx >= 0) {
+        const msg = messages[lastUserIdx];
+        const textContent = typeof msg.content === "string" ? msg.content : "";
+        const parts: Array<{ type: string; text?: string; image?: URL; mimeType?: string }> = [
+          { type: "text", text: textContent },
+        ];
+        for (const att of imageAttachments) {
+          parts.push({
+            type: "image",
+            image: new URL(att.downloadUrl),
+            mimeType: att.contentType,
+          });
+        }
+        messages[lastUserIdx] = { ...msg, content: parts as ModelMessage["content"] };
+      }
+    }
+  }
 
   const chatResponse = await agent.generate({ messages });
   const text = chatResponse.text;
diff --git a/lib/emails/inbound/getEmailAttachments.ts b/lib/emails/inbound/getEmailAttachments.ts
new file mode 100644
index 000000000..fac16d328
--- /dev/null
+++ b/lib/emails/inbound/getEmailAttachments.ts
@@ -0,0 +1,30 @@
+import { getResendClient } from "@/lib/emails/client";
+
+export interface EmailAttachment {
+  id: string;
+  filename: string;
+  contentType: string;
+  downloadUrl: string;
+}
+
+/**
+ * Fetches attachment download URLs for a received email from Resend.
+ * Webhooks only include attachment metadata (id, filename, content_type),
+ * so this calls the Attachments API to get download URLs.
+ *
+ * @param emailId - The email ID from the Resend webhook event
+ * @returns Array of attachments with download URLs (empty if none)
+ */
+export async function getEmailAttachments(emailId: string): Promise<EmailAttachment[]> {
+  const resend = getResendClient();
+  const { data } = await resend.emails.receiving.attachments.list({ emailId });
+
+  if (!data?.data?.length) return [];
+
+  return data.data.map(att => ({
+    id: att.id,
+    filename: att.filename || "attachment",
+    contentType: att.content_type,
+    downloadUrl: att.download_url,
+  }));
+}
diff --git a/lib/emails/inbound/validateNewEmailMemory.ts b/lib/emails/inbound/validateNewEmailMemory.ts
index b062d1b04..ffa91d9a3 100644
--- a/lib/emails/inbound/validateNewEmailMemory.ts
+++ b/lib/emails/inbound/validateNewEmailMemory.ts
@@ -9,6 +9,8 @@ import { RECOUP_API_KEY } from "@/lib/const";
 import { setupConversation } from "@/lib/chat/setupConversation";
 import insertMemoryEmail from "@/lib/supabase/memory_emails/insertMemoryEmail";
 import { trimRepliedContext } from "@/lib/emails/inbound/trimRepliedContext";
+import { getEmailAttachments } from "./getEmailAttachments";
+import { formatAttachmentsText } from "./formatAttachmentsText";
 
 /**
  * Validates and processes a new memory from an inbound email.
@@ -29,7 +31,9 @@ export async function validateNewEmailMemory(
   const accountId = accountEmails[0].account_id;
 
   const emailContent = await getEmailContent(emailId);
-  const emailText = trimRepliedContext(emailContent.html || "");
+  const attachments = await getEmailAttachments(emailId);
+  const emailText =
+    trimRepliedContext(emailContent.html || "") + formatAttachmentsText(attachments);
 
   const roomId = await getEmailRoomId(emailContent);
   const promptMessage = getMessages(emailText)[0];
@@ -72,6 +76,7 @@ export async function validateNewEmailMemory(
     messages: getMessages(emailText),
     roomId: finalRoomId,
     authToken: RECOUP_API_KEY,
+    attachments,
   };
 
   return { chatRequestBody, emailText };

From a9574966cc3f47a22fc0c65cb4fbc5f8fbe19356 Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 11:35:18 -0500
Subject: [PATCH 2/7] fix: resolve TypeScript type error in
 generateEmailResponse

Construct a proper UserModelMessage instead of spreading a generic
ModelMessage, fixing the discriminated union type incompatibility.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 lib/emails/inbound/generateEmailResponse.ts | 16 +++++++---------
 1 file changed, 7 insertions(+), 9 deletions(-)

diff --git a/lib/emails/inbound/generateEmailResponse.ts b/lib/emails/inbound/generateEmailResponse.ts
index 1c9c318f3..87c3fe63b 100644
--- a/lib/emails/inbound/generateEmailResponse.ts
+++ b/lib/emails/inbound/generateEmailResponse.ts
@@ -1,4 +1,4 @@
-import type { ModelMessage } from "ai";
+import type { ModelMessage, UserModelMessage } from "ai";
 import { marked } from "marked";
 import { ChatRequestBody } from "@/lib/chat/validateChatRequest";
 import getGeneralAgent from "@/lib/agents/generalAgent/getGeneralAgent";
@@ -38,17 +38,15 @@ export async function generateEmailResponse(
       if (lastUserIdx >= 0) {
         const msg = messages[lastUserIdx];
         const textContent = typeof msg.content === "string" ? msg.content : "";
-        const parts: Array<{ type: string; text?: string; image?: URL; mimeType?: string }> = [
+        const parts: UserModelMessage["content"] = [
           { type: "text", text: textContent },
-        ];
-        for (const att of imageAttachments) {
-          parts.push({
-            type: "image",
+          ...imageAttachments.map(att => ({
+            type: "image" as const,
             image: new URL(att.downloadUrl),
             mimeType: att.contentType,
-          });
-        }
-        messages[lastUserIdx] = { ...msg, content: parts as ModelMessage["content"] };
+          })),
+        ];
+        messages[lastUserIdx] = { role: "user" as const, content: parts };
       }
     }
   }

From 0a5fb33bc1beb778db2343bc231fb640dba81cc3 Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 11:59:18 -0500
Subject: [PATCH 3/7] refactor: remove image parts, rely on download URLs for
 all file types
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Remove image part injection into agent messages. Attachment download
URLs in the email text are sufficient — OpenClaw in the sandbox can
fetch any file type directly. This avoids signed URL access issues
and unsupported format errors (e.g. SVG) with LLM vision APIs.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 lib/chat/validateChatRequest.ts               |   2 -
 .../__tests__/generateEmailResponse.test.ts   | 103 +-----------------
 .../__tests__/validateNewEmailMemory.test.ts  |  40 ++-----
 lib/emails/inbound/generateEmailResponse.ts   |  28 +----
 lib/emails/inbound/validateNewEmailMemory.ts  |   1 -
 5 files changed, 10 insertions(+), 164 deletions(-)

diff --git a/lib/chat/validateChatRequest.ts b/lib/chat/validateChatRequest.ts
index c2c516be3..92219e6d5 100644
--- a/lib/chat/validateChatRequest.ts
+++ b/lib/chat/validateChatRequest.ts
@@ -11,7 +11,6 @@ import { getApiKeyDetails } from "@/lib/keys/getApiKeyDetails";
 import { validateOrganizationAccess } from "@/lib/organizations/validateOrganizationAccess";
 import { setupConversation } from "@/lib/chat/setupConversation";
 import { validateMessages } from "@/lib/chat/validateMessages";
-import type { EmailAttachment } from "@/lib/emails/inbound/getEmailAttachments";
 
 export const chatRequestSchema = z
   .object({
@@ -51,7 +50,6 @@ export type ChatRequestBody = BaseChatRequestBody & {
   accountId: string;
   orgId: string | null;
   authToken?: string;
-  attachments?: EmailAttachment[];
 };
 
 /**
diff --git a/lib/emails/inbound/__tests__/generateEmailResponse.test.ts b/lib/emails/inbound/__tests__/generateEmailResponse.test.ts
index ed5216ddd..faa3b8e96 100644
--- a/lib/emails/inbound/__tests__/generateEmailResponse.test.ts
+++ b/lib/emails/inbound/__tests__/generateEmailResponse.test.ts
@@ -42,7 +42,7 @@ describe("generateEmailResponse", () => {
     );
   });
 
-  it("generates response without attachments", async () => {
+  it("generates response with text and footer", async () => {
     vi.mocked(getEmailRoomMessages).mockResolvedValue([{ role: "user", content: "Hi there" }]);
 
     const body: ChatRequestBody = {
@@ -61,105 +61,4 @@ describe("generateEmailResponse", () => {
     expect(result.html).toContain("Hello from assistant");
     expect(result.html).toContain("<footer>footer</footer>");
   });
-
-  it("appends image parts to last user message when image attachments exist", async () => {
-    vi.mocked(getEmailRoomMessages).mockResolvedValue([
-      { role: "user", content: "Check this image" },
-    ]);
-
-    const body: ChatRequestBody = {
-      accountId: "acc-1",
-      orgId: null,
-      messages: [],
-      roomId: "room-1",
-      attachments: [
-        {
-          id: "att-1",
-          filename: "logo.png",
-          contentType: "image/png",
-          downloadUrl: "https://resend.com/dl/att-1",
-        },
-      ],
-    };
-
-    await generateEmailResponse(body);
-
-    const callArgs = mockGenerate.mock.calls[0][0];
-    const lastUserMsg = callArgs.messages[0];
-
-    // Should have been converted to parts array with text + image
-    expect(Array.isArray(lastUserMsg.content)).toBe(true);
-    expect(lastUserMsg.content[0]).toEqual({ type: "text", text: "Check this image" });
-    expect(lastUserMsg.content[1]).toMatchObject({
-      type: "image",
-      mimeType: "image/png",
-    });
-    expect(lastUserMsg.content[1].image).toBeInstanceOf(URL);
-    expect(lastUserMsg.content[1].image.href).toBe("https://resend.com/dl/att-1");
-  });
-
-  it("does not modify messages when only non-image attachments exist", async () => {
-    vi.mocked(getEmailRoomMessages).mockResolvedValue([
-      { role: "user", content: "Check this file" },
-    ]);
-
-    const body: ChatRequestBody = {
-      accountId: "acc-1",
-      orgId: null,
-      messages: [],
-      roomId: "room-1",
-      attachments: [
-        {
-          id: "att-1",
-          filename: "report.pdf",
-          contentType: "application/pdf",
-          downloadUrl: "https://resend.com/dl/att-1",
-        },
-      ],
-    };
-
-    await generateEmailResponse(body);
-
-    const callArgs = mockGenerate.mock.calls[0][0];
-    const lastUserMsg = callArgs.messages[0];
-
-    // Should remain as plain string (no image parts to add)
-    expect(lastUserMsg.content).toBe("Check this file");
-  });
-
-  it("appends image parts to the last user message in multi-message conversations", async () => {
-    vi.mocked(getEmailRoomMessages).mockResolvedValue([
-      { role: "user", content: "First message" },
-      { role: "assistant", content: "Reply" },
-      { role: "user", content: "Here is the image" },
-    ]);
-
-    const body: ChatRequestBody = {
-      accountId: "acc-1",
-      orgId: null,
-      messages: [],
-      roomId: "room-1",
-      attachments: [
-        {
-          id: "att-1",
-          filename: "photo.jpg",
-          contentType: "image/jpeg",
-          downloadUrl: "https://resend.com/dl/att-1",
-        },
-      ],
-    };
-
-    await generateEmailResponse(body);
-
-    const callArgs = mockGenerate.mock.calls[0][0];
-    // First user message should be unchanged
-    expect(callArgs.messages[0].content).toBe("First message");
-    // Last user message should have image parts
-    expect(Array.isArray(callArgs.messages[2].content)).toBe(true);
-    expect(callArgs.messages[2].content[0]).toEqual({
-      type: "text",
-      text: "Here is the image",
-    });
-    expect(callArgs.messages[2].content[1].type).toBe("image");
-  });
 });
diff --git a/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts b/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
index 663ad8ecc..3b0ebafd2 100644
--- a/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
+++ b/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
@@ -140,33 +140,7 @@ describe("validateNewEmailMemory", () => {
     expect(response.status).toBe(200);
   });
 
-  it("fetches attachments and includes them in chatRequestBody", async () => {
-    const mockAttachments = [
-      {
-        id: "att-1",
-        filename: "logo.svg",
-        contentType: "image/svg+xml",
-        downloadUrl: "https://resend.com/dl/att-1",
-      },
-    ];
-    vi.mocked(getEmailAttachments).mockResolvedValue(mockAttachments);
-    vi.mocked(formatAttachmentsText).mockReturnValue(
-      "\n\nAttached files:\n- logo.svg (image/svg+xml): https://resend.com/dl/att-1",
-    );
-
-    const event = createMockEvent();
-    const result = await validateNewEmailMemory(event);
-
-    expect(result).not.toHaveProperty("response");
-    const { chatRequestBody } = result as {
-      chatRequestBody: Record<string, unknown>;
-      emailText: string;
-    };
-    expect(chatRequestBody.attachments).toEqual(mockAttachments);
-    expect(getEmailAttachments).toHaveBeenCalledWith(MOCK_EMAIL_ID);
-  });
-
-  it("appends attachment URLs to emailText", async () => {
+  it("fetches attachments and appends download URLs to emailText", async () => {
     const attachmentText =
       "\n\nAttached files:\n- logo.svg (image/svg+xml): https://resend.com/dl/att-1";
     vi.mocked(getEmailAttachments).mockResolvedValue([
@@ -182,22 +156,22 @@ describe("validateNewEmailMemory", () => {
     const event = createMockEvent();
     const result = await validateNewEmailMemory(event);
 
+    expect(result).not.toHaveProperty("response");
+    expect(getEmailAttachments).toHaveBeenCalledWith(MOCK_EMAIL_ID);
+
     const { emailText } = result as { chatRequestBody: Record<string, unknown>; emailText: string };
     expect(emailText).toContain("Attached files:");
     expect(emailText).toContain("https://resend.com/dl/att-1");
   });
 
-  it("includes empty attachments array when no attachments exist", async () => {
+  it("does not append text when no attachments exist", async () => {
     vi.mocked(getEmailAttachments).mockResolvedValue([]);
     vi.mocked(formatAttachmentsText).mockReturnValue("");
 
     const event = createMockEvent();
     const result = await validateNewEmailMemory(event);
 
-    const { chatRequestBody } = result as {
-      chatRequestBody: Record<string, unknown>;
-      emailText: string;
-    };
-    expect(chatRequestBody.attachments).toEqual([]);
+    const { emailText } = result as { chatRequestBody: Record<string, unknown>; emailText: string };
+    expect(emailText).toBe("<p>Hello from email</p>");
   });
 });
diff --git a/lib/emails/inbound/generateEmailResponse.ts b/lib/emails/inbound/generateEmailResponse.ts
index 87c3fe63b..59edf811c 100644
--- a/lib/emails/inbound/generateEmailResponse.ts
+++ b/lib/emails/inbound/generateEmailResponse.ts
@@ -1,4 +1,3 @@
-import type { ModelMessage, UserModelMessage } from "ai";
 import { marked } from "marked";
 import { ChatRequestBody } from "@/lib/chat/validateChatRequest";
 import getGeneralAgent from "@/lib/agents/generalAgent/getGeneralAgent";
@@ -9,7 +8,6 @@ import { selectRoomWithArtist } from "@/lib/supabase/rooms/selectRoomWithArtist"
 /**
  * Generates the assistant response HTML for an email, including:
  * - Running the general agent to generate a reply for the given room
- * - Appending image attachments as visual content parts to the last user message
  * - Fetching the room messages
  * - Appending a standardized footer with reply and link instructions
  *
@@ -19,7 +17,7 @@ import { selectRoomWithArtist } from "@/lib/supabase/rooms/selectRoomWithArtist"
 export async function generateEmailResponse(
   body: ChatRequestBody,
 ): Promise<{ text: string; html: string }> {
-  const { roomId, attachments } = body;
+  const { roomId } = body;
   if (!roomId) {
     throw new Error("roomId is required to generate email response HTML");
   }
@@ -27,29 +25,7 @@ export async function generateEmailResponse(
   const decision = await getGeneralAgent(body);
   const agent = decision.agent;
 
-  const messages: ModelMessage[] = await getEmailRoomMessages(roomId);
-
-  // Append image attachments as visual content parts to the last user message
-  // so the LLM can visually process images (in addition to having download URLs in text)
-  if (attachments?.length) {
-    const imageAttachments = attachments.filter(a => a.contentType.startsWith("image/"));
-    if (imageAttachments.length) {
-      const lastUserIdx = messages.findLastIndex(m => m.role === "user");
-      if (lastUserIdx >= 0) {
-        const msg = messages[lastUserIdx];
-        const textContent = typeof msg.content === "string" ? msg.content : "";
-        const parts: UserModelMessage["content"] = [
-          { type: "text", text: textContent },
-          ...imageAttachments.map(att => ({
-            type: "image" as const,
-            image: new URL(att.downloadUrl),
-            mimeType: att.contentType,
-          })),
-        ];
-        messages[lastUserIdx] = { role: "user" as const, content: parts };
-      }
-    }
-  }
+  const messages = await getEmailRoomMessages(roomId);
 
   const chatResponse = await agent.generate({ messages });
   const text = chatResponse.text;
diff --git a/lib/emails/inbound/validateNewEmailMemory.ts b/lib/emails/inbound/validateNewEmailMemory.ts
index ffa91d9a3..ed0dea756 100644
--- a/lib/emails/inbound/validateNewEmailMemory.ts
+++ b/lib/emails/inbound/validateNewEmailMemory.ts
@@ -76,7 +76,6 @@ export async function validateNewEmailMemory(
     messages: getMessages(emailText),
     roomId: finalRoomId,
     authToken: RECOUP_API_KEY,
-    attachments,
   };
 
   return { chatRequestBody, emailText };

From 1241c869ded5f40b9867285b34d8e2139dceed74 Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 12:18:55 -0500
Subject: [PATCH 4/7] debug: add logging to respondToInboundEmail flow

Logs at each step to identify where the email response pipeline
stops: memory validation, CC check, response generation, and send.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 lib/emails/inbound/respondToInboundEmail.ts | 11 +++++++++++
 1 file changed, 11 insertions(+)

diff --git a/lib/emails/inbound/respondToInboundEmail.ts b/lib/emails/inbound/respondToInboundEmail.ts
index ea75fb3b3..454e973ed 100644
--- a/lib/emails/inbound/respondToInboundEmail.ts
+++ b/lib/emails/inbound/respondToInboundEmail.ts
@@ -19,6 +19,7 @@ export async function respondToInboundEmail(
 ): Promise<NextResponse> {
   try {
     const original = event.data;
+    const emailId = original.email_id;
     const subject = original.subject ? `Re: ${original.subject}` : "Re: Your email";
     const messageId = original.message_id;
     const to = original.from;
@@ -26,23 +27,30 @@ export async function respondToInboundEmail(
     const from = getFromWithName(original.to, original.cc);
     const cc = original.cc?.length ? original.cc : undefined;
 
+    console.log(`[respondToInboundEmail] Processing email ${emailId} from ${to}`);
+
     // Validate new memory and get chat request body (or early return if duplicate)
     const validationResult = await validateNewEmailMemory(event);
     if ("response" in validationResult) {
+      console.log(`[respondToInboundEmail] Email ${emailId} - early return from validateNewEmailMemory`);
       return validationResult.response;
     }
 
     const { chatRequestBody, emailText } = validationResult;
+    console.log(`[respondToInboundEmail] Email ${emailId} - memory validated, roomId=${chatRequestBody.roomId}, emailText length=${emailText.length}`);
 
     // Check if Recoup is only CC'd - use LLM to determine if reply is expected
     const ccValidation = await validateCcReplyExpected(original, emailText);
     if (ccValidation) {
+      console.log(`[respondToInboundEmail] Email ${emailId} - CC validation returned early (not a direct reply)`);
       return ccValidation.response;
     }
 
     const { roomId } = chatRequestBody;
 
+    console.log(`[respondToInboundEmail] Email ${emailId} - generating response...`);
     const { text, html } = await generateEmailResponse(chatRequestBody);
+    console.log(`[respondToInboundEmail] Email ${emailId} - response generated, text length=${text.length}`);
 
     const payload = {
       from,
@@ -55,15 +63,18 @@ export async function respondToInboundEmail(
       },
     };
 
+    console.log(`[respondToInboundEmail] Email ${emailId} - sending reply to ${to} from ${from}`);
     const result = await sendEmailWithResend(payload);
 
     // Save the assistant response message
     await saveChatCompletion({ text, roomId });
 
     if (result instanceof NextResponse) {
+      console.log(`[respondToInboundEmail] Email ${emailId} - sendEmailWithResend returned error response`);
       return result;
     }
 
+    console.log(`[respondToInboundEmail] Email ${emailId} - reply sent successfully`);
     return NextResponse.json(result);
   } catch (error) {
     console.error("[respondToInboundEmail] Failed to respond to inbound email", error);

From 8b958edd2b16bc44e0510a6d40c6b99b109703da Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 12:30:39 -0500
Subject: [PATCH 5/7] feat: instruct OpenClaw to download attachment URLs
 before storing

Attachment download URLs from email are temporary (expire in 1 hour).
Add sandbox prompt note telling OpenClaw to always download files
locally via curl instead of storing the raw URL in repo files.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 lib/chat/tools/createPromptSandboxStreamingTool.ts | 6 +++++-
 1 file changed, 5 insertions(+), 1 deletion(-)

diff --git a/lib/chat/tools/createPromptSandboxStreamingTool.ts b/lib/chat/tools/createPromptSandboxStreamingTool.ts
index f5a65eac6..03cd7b372 100644
--- a/lib/chat/tools/createPromptSandboxStreamingTool.ts
+++ b/lib/chat/tools/createPromptSandboxStreamingTool.ts
@@ -4,7 +4,11 @@ import { promptSandboxStreaming } from "@/lib/sandbox/promptSandboxStreaming";
 
 export const SANDBOX_PROMPT_NOTE =
   "IMPORTANT: When you make changes to any files inside the orgs/ directory, " +
-  "always commit and push those changes directly to main so they are preserved and shared across sessions.";
+  "always commit and push those changes directly to main so they are preserved and shared across sessions.\n\n" +
+  "IMPORTANT: When a prompt includes attached file URLs (e.g. from email attachments), " +
+  "always download the files first using curl and save them locally before referencing them. " +
+  "These URLs are temporary and expire after 1 hour. Never store the download URL directly in files — " +
+  "download the content, save it to the appropriate location in the repo, and reference the local path instead.";
 
 const promptSandboxSchema = z.object({
   prompt: z.string().min(1).describe("The prompt to send to OpenClaw running in the sandbox."),

From 35b480b3d279bb0b404c47fb2ff077e4dfa922da Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 12:46:41 -0500
Subject: [PATCH 6/7] refactor: use Resend SDK type for EmailAttachment instead
 of custom interface
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Replace the custom EmailAttachment interface with
ListAttachmentsResponseSuccess["data"][number] from the Resend SDK.
Remove the camelCase remapping layer — return SDK objects directly.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 .../__tests__/formatAttachmentsText.test.ts   | 50 +++++++++++++------
 .../__tests__/getEmailAttachments.test.ts     | 42 ++--------------
 .../__tests__/validateNewEmailMemory.test.ts  |  9 ++--
 lib/emails/inbound/formatAttachmentsText.ts   |  2 +-
 lib/emails/inbound/getEmailAttachments.ts     | 15 ++----
 5 files changed, 49 insertions(+), 69 deletions(-)

diff --git a/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts b/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts
index 820a3247c..c0bc2129f 100644
--- a/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts
+++ b/lib/emails/inbound/__tests__/formatAttachmentsText.test.ts
@@ -2,19 +2,30 @@ import { describe, it, expect } from "vitest";
 import { formatAttachmentsText } from "../formatAttachmentsText";
 import type { EmailAttachment } from "../getEmailAttachments";
 
+const makeAttachment = (overrides: Partial<EmailAttachment> = {}): EmailAttachment =>
+  ({
+    id: "att-1",
+    filename: "file.txt",
+    size: 1024,
+    content_type: "text/plain",
+    content_disposition: "attachment",
+    download_url: "https://resend.com/dl/att-1",
+    expires_at: "2025-01-01T01:00:00Z",
+    ...overrides,
+  }) as EmailAttachment;
+
 describe("formatAttachmentsText", () => {
   it("returns empty string for empty array", () => {
     expect(formatAttachmentsText([])).toBe("");
   });
 
   it("formats a single attachment", () => {
-    const attachments: EmailAttachment[] = [
-      {
-        id: "att-1",
+    const attachments = [
+      makeAttachment({
         filename: "logo.svg",
-        contentType: "image/svg+xml",
-        downloadUrl: "https://resend.com/dl/att-1",
-      },
+        content_type: "image/svg+xml",
+        download_url: "https://resend.com/dl/att-1",
+      }),
     ];
 
     const result = formatAttachmentsText(attachments);
@@ -25,19 +36,18 @@ describe("formatAttachmentsText", () => {
   });
 
   it("formats multiple attachments", () => {
-    const attachments: EmailAttachment[] = [
-      {
-        id: "att-1",
+    const attachments = [
+      makeAttachment({
         filename: "logo.svg",
-        contentType: "image/svg+xml",
-        downloadUrl: "https://resend.com/dl/att-1",
-      },
-      {
+        content_type: "image/svg+xml",
+        download_url: "https://resend.com/dl/att-1",
+      }),
+      makeAttachment({
         id: "att-2",
         filename: "report.pdf",
-        contentType: "application/pdf",
-        downloadUrl: "https://resend.com/dl/att-2",
-      },
+        content_type: "application/pdf",
+        download_url: "https://resend.com/dl/att-2",
+      }),
     ];
 
     const result = formatAttachmentsText(attachments);
@@ -46,4 +56,12 @@ describe("formatAttachmentsText", () => {
     expect(result).toContain("- logo.svg (image/svg+xml): https://resend.com/dl/att-1");
     expect(result).toContain("- report.pdf (application/pdf): https://resend.com/dl/att-2");
   });
+
+  it("defaults filename to 'attachment' when not provided", () => {
+    const attachments = [makeAttachment({ filename: undefined })];
+
+    const result = formatAttachmentsText(attachments);
+
+    expect(result).toContain("- attachment (text/plain):");
+  });
 });
diff --git a/lib/emails/inbound/__tests__/getEmailAttachments.test.ts b/lib/emails/inbound/__tests__/getEmailAttachments.test.ts
index 537b4dfce..042001dc5 100644
--- a/lib/emails/inbound/__tests__/getEmailAttachments.test.ts
+++ b/lib/emails/inbound/__tests__/getEmailAttachments.test.ts
@@ -23,7 +23,7 @@ describe("getEmailAttachments", () => {
     } as ReturnType<typeof getResendClient>);
   });
 
-  it("returns mapped attachments when Resend returns data", async () => {
+  it("returns attachments directly from Resend SDK", async () => {
     mockList.mockResolvedValue({
       data: {
         data: [
@@ -52,20 +52,10 @@ describe("getEmailAttachments", () => {
     const result = await getEmailAttachments("email-123");
 
     expect(mockList).toHaveBeenCalledWith({ emailId: "email-123" });
-    expect(result).toEqual([
-      {
-        id: "att-1",
-        filename: "logo.svg",
-        contentType: "image/svg+xml",
-        downloadUrl: "https://resend.com/dl/att-1",
-      },
-      {
-        id: "att-2",
-        filename: "report.pdf",
-        contentType: "application/pdf",
-        downloadUrl: "https://resend.com/dl/att-2",
-      },
-    ]);
+    expect(result).toHaveLength(2);
+    expect(result[0].id).toBe("att-1");
+    expect(result[0].download_url).toBe("https://resend.com/dl/att-1");
+    expect(result[1].content_type).toBe("application/pdf");
   });
 
   it("returns empty array when no attachments exist", async () => {
@@ -83,26 +73,4 @@ describe("getEmailAttachments", () => {
 
     expect(result).toEqual([]);
   });
-
-  it("defaults filename to 'attachment' when not provided", async () => {
-    mockList.mockResolvedValue({
-      data: {
-        data: [
-          {
-            id: "att-3",
-            filename: undefined,
-            content_type: "application/octet-stream",
-            download_url: "https://resend.com/dl/att-3",
-            size: 512,
-            content_disposition: "attachment",
-            expires_at: "2025-01-01T01:00:00Z",
-          },
-        ],
-      },
-    });
-
-    const result = await getEmailAttachments("email-123");
-
-    expect(result[0].filename).toBe("attachment");
-  });
 });
diff --git a/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts b/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
index 3b0ebafd2..17c164d41 100644
--- a/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
+++ b/lib/emails/inbound/__tests__/validateNewEmailMemory.test.ts
@@ -147,10 +147,13 @@ describe("validateNewEmailMemory", () => {
       {
         id: "att-1",
         filename: "logo.svg",
-        contentType: "image/svg+xml",
-        downloadUrl: "https://resend.com/dl/att-1",
+        size: 1024,
+        content_type: "image/svg+xml",
+        content_disposition: "attachment",
+        download_url: "https://resend.com/dl/att-1",
+        expires_at: "2025-01-01T01:00:00Z",
       },
-    ]);
+    ] as Awaited<ReturnType<typeof getEmailAttachments>>);
     vi.mocked(formatAttachmentsText).mockReturnValue(attachmentText);
 
     const event = createMockEvent();
diff --git a/lib/emails/inbound/formatAttachmentsText.ts b/lib/emails/inbound/formatAttachmentsText.ts
index 9674fcb06..341717be9 100644
--- a/lib/emails/inbound/formatAttachmentsText.ts
+++ b/lib/emails/inbound/formatAttachmentsText.ts
@@ -12,7 +12,7 @@ export function formatAttachmentsText(attachments: EmailAttachment[]): string {
   if (!attachments.length) return "";
 
   const lines = attachments.map(
-    att => `- ${att.filename} (${att.contentType}): ${att.downloadUrl}`,
+    att => `- ${att.filename || "attachment"} (${att.content_type}): ${att.download_url}`,
   );
   return `\n\nAttached files:\n${lines.join("\n")}`;
 }
diff --git a/lib/emails/inbound/getEmailAttachments.ts b/lib/emails/inbound/getEmailAttachments.ts
index fac16d328..c2546f9c8 100644
--- a/lib/emails/inbound/getEmailAttachments.ts
+++ b/lib/emails/inbound/getEmailAttachments.ts
@@ -1,11 +1,7 @@
 import { getResendClient } from "@/lib/emails/client";
+import type { ListAttachmentsResponseSuccess } from "resend";
 
-export interface EmailAttachment {
-  id: string;
-  filename: string;
-  contentType: string;
-  downloadUrl: string;
-}
+export type EmailAttachment = ListAttachmentsResponseSuccess["data"][number];
 
 /**
  * Fetches attachment download URLs for a received email from Resend.
@@ -21,10 +17,5 @@ export async function getEmailAttachments(emailId: string): Promise<EmailAttachm
 
   if (!data?.data?.length) return [];
 
-  return data.data.map(att => ({
-    id: att.id,
-    filename: att.filename || "attachment",
-    contentType: att.content_type,
-    downloadUrl: att.download_url,
-  }));
+  return data.data;
 }

From d5c0df6d42f7506e8feaa784fbb8ada1d0489f92 Mon Sep 17 00:00:00 2001
From: Sweets Sweetman <sweetmantech@gmail.com>
Date: Sat, 28 Feb 2026 12:47:01 -0500
Subject: [PATCH 7/7] chore: remove debug logging from respondToInboundEmail

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 lib/emails/inbound/respondToInboundEmail.ts | 11 -----------
 1 file changed, 11 deletions(-)

diff --git a/lib/emails/inbound/respondToInboundEmail.ts b/lib/emails/inbound/respondToInboundEmail.ts
index 454e973ed..ea75fb3b3 100644
--- a/lib/emails/inbound/respondToInboundEmail.ts
+++ b/lib/emails/inbound/respondToInboundEmail.ts
@@ -19,7 +19,6 @@ export async function respondToInboundEmail(
 ): Promise<NextResponse> {
   try {
     const original = event.data;
-    const emailId = original.email_id;
     const subject = original.subject ? `Re: ${original.subject}` : "Re: Your email";
     const messageId = original.message_id;
     const to = original.from;
@@ -27,30 +26,23 @@ export async function respondToInboundEmail(
     const from = getFromWithName(original.to, original.cc);
     const cc = original.cc?.length ? original.cc : undefined;
 
-    console.log(`[respondToInboundEmail] Processing email ${emailId} from ${to}`);
-
     // Validate new memory and get chat request body (or early return if duplicate)
     const validationResult = await validateNewEmailMemory(event);
     if ("response" in validationResult) {
-      console.log(`[respondToInboundEmail] Email ${emailId} - early return from validateNewEmailMemory`);
       return validationResult.response;
     }
 
     const { chatRequestBody, emailText } = validationResult;
-    console.log(`[respondToInboundEmail] Email ${emailId} - memory validated, roomId=${chatRequestBody.roomId}, emailText length=${emailText.length}`);
 
     // Check if Recoup is only CC'd - use LLM to determine if reply is expected
     const ccValidation = await validateCcReplyExpected(original, emailText);
     if (ccValidation) {
-      console.log(`[respondToInboundEmail] Email ${emailId} - CC validation returned early (not a direct reply)`);
       return ccValidation.response;
     }
 
     const { roomId } = chatRequestBody;
 
-    console.log(`[respondToInboundEmail] Email ${emailId} - generating response...`);
     const { text, html } = await generateEmailResponse(chatRequestBody);
-    console.log(`[respondToInboundEmail] Email ${emailId} - response generated, text length=${text.length}`);
 
     const payload = {
       from,
@@ -63,18 +55,15 @@ export async function respondToInboundEmail(
       },
     };
 
-    console.log(`[respondToInboundEmail] Email ${emailId} - sending reply to ${to} from ${from}`);
     const result = await sendEmailWithResend(payload);
 
     // Save the assistant response message
     await saveChatCompletion({ text, roomId });
 
     if (result instanceof NextResponse) {
-      console.log(`[respondToInboundEmail] Email ${emailId} - sendEmailWithResend returned error response`);
       return result;
     }
 
-    console.log(`[respondToInboundEmail] Email ${emailId} - reply sent successfully`);
     return NextResponse.json(result);
   } catch (error) {
     console.error("[respondToInboundEmail] Failed to respond to inbound email", error);