From 1f4b0669ca7466acfff0afdf51532824905e9cf3 Mon Sep 17 00:00:00 2001
From: Linus Rath <139418639+rathlinus@users.noreply.github.com>
Date: Wed, 4 Nov 2026 05:38:43 +0100
Subject: [PATCH] feat: ask between a new message and Files for a file opened
 with the desktop app

---
 lib/desktop/__tests__/os-commands.test.ts | 17 +++++++++++++++++
 lib/desktop/os-commands.ts                |  6 +++++-
 lib/desktop/types.ts                      |  3 ++-
 3 files changed, 24 insertions(+), 2 deletions(-)

diff --git a/lib/desktop/__tests__/os-commands.test.ts b/lib/desktop/__tests__/os-commands.test.ts
index 35338c572..0410e2ce6 100644
--- a/lib/desktop/__tests__/os-commands.test.ts
+++ b/lib/desktop/__tests__/os-commands.test.ts
@@ -114,6 +114,23 @@ describe('launches', () => {
     expect(draft?.files.map((file) => file.name)).toEqual(['report.pdf']);
   });
 
+  it('several files sent to the app go on one draft, without a question', async () => {
+    const { takeHandoff } = await import('@/lib/launch-handoff');
+    await run({ type: 'files', reason: 'attach', failed: [], files: [{ name: 'a.pdf', data: text('a') }, { name: 'b.png', data: text('b') }] });
+    expect(takeHandoff('compose')?.files.map((file) => file.name)).toEqual(['a.pdf', 'b.png']);
+  });
+
+  it('a file opened with the app asks: new message or Files, a new message first', async () => {
+    const { takeHandoff } = await import('@/lib/launch-handoff');
+    const { listenForFileChoices } = await import('@/lib/file-drop/choice');
+    const asked = vi.fn();
+    const stop = listenForFileChoices(asked);
+    await run({ type: 'files', reason: 'attach', ask: true, failed: [], files: [{ name: 'report.pdf', data: text('pdf') }] });
+    expect(asked).toHaveBeenCalledWith({ files: [expect.objectContaining({ name: 'report.pdf' })], preferred: 'new-message' });
+    expect(takeHandoff('compose')).toBeNull();
+    stop();
+  });
+
   it('says so when a file could not be read', async () => {
     await run({ type: 'files', reason: 'open', failed: ['gone.eml'], files: [] });
     expect(notifyFailed).toHaveBeenCalledWith(['gone.eml']);
diff --git a/lib/desktop/os-commands.ts b/lib/desktop/os-commands.ts
index c52c1baad..5209e07ea 100644
--- a/lib/desktop/os-commands.ts
+++ b/lib/desktop/os-commands.ts
@@ -9,6 +9,7 @@ import { isAppLocked } from '@/lib/desktop/app-lock-state';
 import { getDesktopBridge } from '@/lib/desktop/bridge';
 import type { DesktopOsCommand } from '@/lib/desktop/types';
 import { openMailLink } from '@/lib/desktop/mail-links';
+import { requestFileChoice } from '@/lib/file-drop/choice';
 import { handleReminderCommand } from '@/lib/desktop/reminder-notifications';
 import type { MailNotificationContext } from '@/lib/desktop/mail-notifications';
 import { handOffDraft, handOffFiles, handOffNewMessage, kindForFile } from '@/lib/launch-handoff';
@@ -131,7 +132,10 @@ async function handleNotification(action: string, rawContext: string, reply: str
 function handleFiles(command: Extract<DesktopOsCommand, { type: 'files' }>, env: OsCommandEnv): void {
   const made = command.files.map(({ name, data }) => new File([new Uint8Array(data)], name));
   const failed = [...command.failed];
-  if (command.reason === 'attach') {
+  if (command.reason === 'attach' && command.ask) {
+    // Opened with the app ("Open with"): the same choice as dropping it on the window.
+    requestFileChoice({ files: made, preferred: 'new-message' });
+  } else if (command.reason === 'attach') {
     if (made.length > 0) handOffDraft({ files: made });
   } else {
     for (const file of made) {
diff --git a/lib/desktop/types.ts b/lib/desktop/types.ts
index 69cbd18c0..9bbdfdbc8 100644
--- a/lib/desktop/types.ts
+++ b/lib/desktop/types.ts
@@ -550,7 +550,8 @@ export type DesktopOsCommand =
   | { type: 'open-mailbox'; mailboxId: string }
   | { type: 'mailto'; url: string }
   | { type: 'webcal'; url: string }
-  | { type: 'files'; reason: 'open' | 'attach'; files: DesktopOsFile[]; failed: string[] }
+  /** `ask`: opened with the app, so the user picks between a new message and Files. Without it, attach. */
+  | { type: 'files'; reason: 'open' | 'attach'; files: DesktopOsFile[]; failed: string[]; ask?: boolean }
   | { type: 'notification'; action: string; context: string; reply?: string };
 
 export interface DesktopOsNotification {