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feat: add quoting support to gmail.createDraft #360

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795343e
feat: add quoting support to gmail.createDraft tool
mickey-mikey May 5, 2026
d3186ad
fix: use base64url and tolerate CRLF in createDraft quoting
claude May 5, 2026
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305 changes: 305 additions & 0 deletions workspace-server/src/__tests__/services/GmailService.test.ts
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Original file line number Diff line number Diff line change
Expand Up @@ -822,6 +822,9 @@ describe('GmailService', () => {
(MimeHelper.createMimeMessage as jest.Mock) = jest
.fn()
.mockReturnValue('base64encodedmessage');
(MimeHelper.buildQuotedBlock as jest.Mock) = jest
.fn()
.mockReturnValue('\r\n\r\nQUOTED_BLOCK');
});

it('should create a draft email', async () => {
Expand Down Expand Up @@ -994,6 +997,308 @@ describe('GmailService', () => {
const response = JSON.parse(result.content[0].text);
expect(response.status).toBe('draft_created');
});

it('should fetch quoted message and append quote block to body', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });

mockGmailAPI.users.threads.get.mockResolvedValue({
data: {
messages: [
{
id: 'msg1',
payload: {
headers: [
{ name: 'Message-ID', value: '<msg1@example.com>' },
{ name: 'From', value: 'original@example.com' },
{ name: 'Date', value: 'Mon, 5 May 2026 10:00:00 +0000' },
{ name: 'References', value: '<ref1@example.com>' },
],
parts: [
{
mimeType: 'text/plain',
body: {
data: Buffer.from('Original message body').toString('base64'),
},
},
],
},
},
],
},
});

const result = await gmailService.createDraft({
to: 'recipient@example.com',
subject: 'Re: Test',
body: 'My reply',
threadId: 'thread1',
quoteOriginal: true,
});

expect(mockGmailAPI.users.threads.get).toHaveBeenCalledWith(
expect.objectContaining({
format: 'full',
}),
);

expect(MimeHelper.buildQuotedBlock).toHaveBeenCalledWith(
expect.objectContaining({
originalBody: 'Original message body',
from: 'original@example.com',
date: 'Mon, 5 May 2026 10:00:00 +0000',
isHtml: false,
}),
);

expect(MimeHelper.createMimeMessage).toHaveBeenCalledWith(
expect.objectContaining({
body: 'My reply\r\n\r\nQUOTED_BLOCK',
}),
);

const response = JSON.parse(result.content[0].text);
expect(response.status).toBe('draft_created');
});

it('should prefer text/plain body for plain-text drafts when both exist', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });

mockGmailAPI.users.threads.get.mockResolvedValue({
data: {
messages: [
{
id: 'msg1',
payload: {
headers: [
{ name: 'From', value: 'sender@example.com' },
{ name: 'Date', value: 'Date' },
],
parts: [
{
mimeType: 'text/plain',
body: { data: Buffer.from('Plain text').toString('base64') },
},
{
mimeType: 'text/html',
body: { data: Buffer.from('<p>HTML</p>').toString('base64') },
},
],
},
},
],
},
});

await gmailService.createDraft({
to: 'test@example.com',
subject: 'Test',
body: 'Reply',
threadId: 'thread1',
quoteOriginal: true,
});

expect(MimeHelper.buildQuotedBlock).toHaveBeenCalledWith(
expect.objectContaining({
originalBody: 'Plain text',
}),
);
});

it('should fall back to stripped HTML when only HTML body available for plain-text draft', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });
mockGmailAPI.users.threads.get.mockResolvedValue({
data: {
messages: [
{
id: 'msg1',
payload: {
headers: [
{ name: 'From', value: 'sender@example.com' },
{ name: 'Date', value: 'Test Date' },
{ name: 'Message-ID', value: '<msg1@example.com>' },
],
parts: [
{
mimeType: 'text/html',
body: {
data: Buffer.from('<p>HTML content</p>').toString('base64'),
},
},
],
},
},
],
},
});

await gmailService.createDraft({
to: 'test@example.com',
subject: 'Test',
body: 'Reply',
threadId: 'thread1',
quoteOriginal: true,
isHtml: false,
});

expect(MimeHelper.createMimeMessage).toHaveBeenCalledWith(
expect.objectContaining({
body: expect.stringContaining('Reply'),
}),
);
});

it('should prefer text/html body for HTML drafts', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });

mockGmailAPI.users.threads.get.mockResolvedValue({
data: {
messages: [
{
id: 'msg1',
payload: {
headers: [
{ name: 'From', value: 'sender@example.com' },
{ name: 'Date', value: 'Date' },
],
parts: [
{
mimeType: 'text/plain',
body: { data: Buffer.from('Plain').toString('base64') },
},
{
mimeType: 'text/html',
body: { data: Buffer.from('<p>HTML</p>').toString('base64') },
},
],
},
},
],
},
});

await gmailService.createDraft({
to: 'test@example.com',
subject: 'Test',
body: 'Reply',
threadId: 'thread1',
quoteOriginal: true,
isHtml: true,
});

expect(MimeHelper.buildQuotedBlock).toHaveBeenCalledWith(
expect.objectContaining({
originalBody: '<p>HTML</p>',
isHtml: true,
}),
);
});

it('should gracefully degrade if quoted message fetch fails', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });

mockGmailAPI.users.threads.get.mockRejectedValue(new Error('Failed to fetch'));

const result = await gmailService.createDraft({
to: 'test@example.com',
subject: 'Test',
body: 'Reply body',
threadId: 'thread1',
quoteOriginal: true,
});

expect(MimeHelper.createMimeMessage).toHaveBeenCalledWith(
expect.objectContaining({
body: 'Reply body',
}),
);

const response = JSON.parse(result.content[0].text);
expect(response.status).toBe('draft_created');
});

it('should work with both threadId and quoteOriginal simultaneously', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });

mockGmailAPI.users.threads.get.mockResolvedValue({
data: {
messages: [
{
id: 'msg1',
payload: {
headers: [
{ name: 'Message-ID', value: '<msg1@example.com>' },
{ name: 'From', value: 'sender@example.com' },
{ name: 'Date', value: 'Date' },
{ name: 'References', value: '<ref@example.com>' },
],
parts: [
{
mimeType: 'text/plain',
body: { data: Buffer.from('Original').toString('base64') },
},
],
},
},
],
},
});

await gmailService.createDraft({
to: 'test@example.com',
subject: 'Re: Test',
body: 'Reply',
threadId: 'thread1',
quoteOriginal: true,
});

expect(MimeHelper.createMimeMessage).toHaveBeenCalledWith(
expect.objectContaining({
inReplyTo: '<msg1@example.com>',
references: '<ref@example.com> <msg1@example.com>',
body: 'Reply\r\n\r\nQUOTED_BLOCK',
}),
);
});

it('should not fetch full thread when quoteOriginal is false or absent', async () => {
const mockDraft = { id: 'draft1', message: { id: 'msg1', threadId: 'thread1' } };
mockGmailAPI.users.drafts.create.mockResolvedValue({ data: mockDraft });

mockGmailAPI.users.threads.get.mockResolvedValue({
data: {
messages: [
{
id: 'msg1',
payload: {
headers: [
{ name: 'Message-ID', value: '<msg1@example.com>' },
],
},
},
],
},
});

await gmailService.createDraft({
to: 'test@example.com',
subject: 'Test',
body: 'Body',
threadId: 'thread1',
});

expect(mockGmailAPI.users.threads.get).toHaveBeenCalledWith(
expect.objectContaining({
format: 'metadata',
metadataHeaders: ['Message-ID', 'References'],
}),
);
});
});

describe('sendDraft', () => {
Expand Down
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