- After writing a new message, press Command–Shift–A to open the Attach dialog.
- You’ll be placed in the file browser. Press Shift–Tab once to move to the sidebar, where you’ll find a list of directories. Choose the directory that contains the file you want to attach (for example, Desktop).
- Press Tab once to return to the file browser. The keyboard focus will now be there. You can confirm this by pressing Control–Option–F4. The VoiceOver cursor will also be on the currently highlighted file, which you can verify by pressing Control–Option–F3.
- Use the arrow keys to highlight the file you want to attach.
- If you press Tab once more, you’ll reach a checkbox labeled Send Windows-friendly attachments. (If you’re sending to a Windows machine, checking this box may be helpful, though its exact function isn’t fully clear.)
- Tab to the Choose File button and press Control–Option–Spacebar.
- You’ll be placed back in your message. If your VoiceOver cursor is still on the first line, you’ll hear the name of the attachment when you read that line.
- Keep in mind: the attachment name will be read wherever the VoiceOver cursor is located.
- When you’re ready to send, press Command–Shift–D.
Sincerely,
JohnyTheHess & WillieTheWoof