macOS Monterey: Remove Attachments is grayed out in Mail

Question

macOS Monterey: Remove Attachments is grayed out in Mail

My old Mac never had this problem, but my new Monterey MacBook Pro does: I can't Remove Attachments on any mail I receive.

FWIW: I use POP (deleting from server). I have tried Rebuilding mailboxes, as well as moving offending messages to different boxes. (Size of attachment makes no difference. Nor does whether I have saved the attachment or not.)

Two situations where I CAN still Remove Attachments:

• From outgoing messages I send, sitting in my Sent box. In fact, if I forward an offending message back to myself, the version in my Sent box gains the ability to Remove Attachments (leaving a weird small 100kb attachment I can live with). But the received copy still can't do it.

• Old messages imported (as mbox files) into my Inbox from my ancient Mac running an old version of Mail. Remove Attachments is fine for old messages—I just can do it for any NEW arrivals on this machine. (Same email account worked fine on the old Mac I just switched from.)

Sounds like this may be an issue going back years... since Mojave maybe? Has any solution emerged? TIA!

Posted on Mar 29, 2022 7:03 PM

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Answer 1

Mar 31, 2022 5:26 PM in response to DiZoE

Good question. It's specifically a UI bug in the Mail app: the menu command is grayed out when it should be available (one message selected, which has an attachment).

Mail DOES recognize the attachment is present: the email shows the "paperclip" icon in the list, and the hover menu at the top of the message works for saving the attachment. I just can't Remove Attachments. Except, as I say, in my Sent box, or for old messages moved from my pre-Monterey Mac.

I have another POP account too, so I just tested that: same problem.

And I have Yahoo (IMAP): IMAP does NOT have the problem. Only POP does.

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Answer 2

DiZoE

Level 4

3,033 points

Mar 30, 2022 9:56 PM in response to Morgan Adams1

Hey Morgan Adams1!

Just a few questions....Do you have multiple emails accounts? And if so, do you see the same behavior on other, or all accounts?

Likewise, do you see the same behavior (if available) in other apps, or webmail?

Likewise, is the Remove Attachments option just not available? Or does mail just not respond at all to the command?

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Answer 3

DiZoE

Level 4

3,033 points

Mar 31, 2022 8:57 PM in response to Morgan Adams1

Interesting.....so the Mail app appears to work as expected....at least for IMAP accounts, but not POP accounts? So the app is working as expected to some degree, wondering if it’s an issue with your accounts, or just a conflict with the email providers utilizing Apple Mail client and Vice versa.

Ate you able to re-create the problem on other Apple Macs? I know your old Mac worked fine, but do you still have it and is it in Monterey?

I know iOS and webmail probably don’t have a feature just like this, (Maybe they do), but if now, can you possibly test in Safe Mode, and/or a new User account on your Mac?

Sorry, wish I had a more direct solution, but have never come across this problem, and those steps may help to narrow down a cause, good luck!

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Answer 4

mikeg28806

Community Specialist

Mar 30, 2022 2:58 PM in response to Morgan Adams1

Hi Morgan Adams1

If you want to delete attachments for messages in the Mail app in macOS Monterey, complete the following steps:

In the Mail app on your Mac, select a message that includes one or more attachments.Choose Message > Remove Attachments.The message remains in the mailbox and is annotated to indicate that all attachments were manually removed.

The following page offers additional information that may be helpful: View, save, or delete email attachments in Mail on Mac

We hope this helps!

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Answer 5

Mar 30, 2022 9:28 PM in response to mikeg28806

I already know how to do it, I've done it for years—but it doesn't work on my new Monterey Mac.

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macOS Monterey: Remove Attachments is grayed out in Mail

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