If someone sends me an email containing a PDF attachment (or a JPG, or another image format...) I know that, on an iPad, I can markup the attachment and then send the marked-up document in a reply to the sender. But what if the email contains two PDFs? Is there a way to mark up the first, return to the original email, mark up the second, then send a reply containing both marked-up documents?

1 Answer 1


I do this all the time.

  1. Save both to Files
  2. Mark up with abandon
  3. Reply and attach

This works in Outlook, native mail, and the fastmail iOS/iPadOS app.

  • 1
    This obviously works, and solves my problem, but there's something very fluid about tapping an attachment, marking it up, and sending it back without ever having to leave Mail, and I was hoping for a similar workflow here.
    – mweiss
    Commented Jun 7, 2020 at 19:00

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