Apple Mail not including attachments in replies

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Level 1

10 points

Apple Mail not including attachments in replies

Hey apple, this is a BIG problem. It has inpacted my job. I have it selected under edit to always send attachment with replies, but it doesn't. My boss kept fussing at me because all messages and attachments were suppose to show everytime I sent them a response. I tried all day to figure out what why it was doing it to no avail. Research shows others have had this problem as well. PLEASE fix this. Thank you

[Re-Titled by Moderator]

Original Title: Attachments when replying

MacBook Pro 16″, macOS 15.5

Posted on Jul 7, 2025 03:39 PM

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Answer 1

andysims

Level 2

227 points

Jul 7, 2025 11:17 PM in response to doelfr

Try this:

Go to Settings > Apps > Mails > Include Attachments with Replies (under Composing) > select Always

If this doesn’t work, there might be a couple of things going on:

Make sure the setting you’re referring to is definitely activated. Even though it seems set, sometimes a simple restart of Mail (or even your computer) can help reset any weird glitches.
If the issue persists, it might be worth checking if your email server or any security software is interfering with attachments. Some mail systems might block attachments in replies automatically.
If nothing works, try removing the account from Mail and adding it back, this can sometimes clear up issues like this.
If that still doesn’t do the trick, reaching out to Apple Support would be the next step to troubleshoot any deeper issues with Mail.

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