Whenever I send an e-mail from Mail.app to someone with Outlook, they can't read any text that is placed beneath an inline attachment.

When I send an e-mail to myself from Mail.app any text that is placed beneath an inline attachment is attached as text-files.

This is very annoying, does anyone know how to fix this problem?

  • This is a well know bug. "Always send Windows-friend attachments." will not do the tricks neither "Always Insert Attachments Beneath Message".
    – gagarine
    Commented Oct 4, 2022 at 15:13

2 Answers 2


Under Edit > Attachments, check Always send Windows-friend attachments.

That way, the text beneath the attachment won't be cut off.

Alternatively, you can do that on a per-message basis in the attachment file selector window, like so:

mail attachment window

  • 1
    That one is checked. Same result.
    – timkl
    Commented Dec 7, 2011 at 12:37
  • 2
    However, there's also an option to Always Insert Attachments Beneath Message. I'll just check that one for now.
    – timkl
    Commented Dec 7, 2011 at 12:40
  • I answer it myself. @timkl to bad you didn't answer in the bounty delay, I would have accepted your comment slightly expanded has an answer.
    – gagarine
    Commented Oct 11, 2022 at 22:11

Their is no solution. A workaround is to insert attachments at the end of the message.

You can set that as this as a default:

  • For the current message: Choose Edit > Attachments > Insert Attachments at End.
  • For all messages: From the Message viewer, choose Edit > Attachments > Always Insert Attachments at End of Message (a tick shows it’s on).

This is not a solution because you loose the benefit of inline attachment. It's also problematic if you have conversation where you recopies the past answer in the body of your email.

Note the "send Windows-Friendly Attachments" option do not fix the problem.

Please report this bug to https://www.apple.com/feedback/mail.html . All other major email client are capable of sending inline attachment to outlook without this issues. Apple Mail can only send attachment inline which make this issue terrible.

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