Mac Mail Won't Attach Anything

In the Mac Mail app, I'm trying to attach some PDFs and images to a draft and neither the paperclip icon nor File->Attach Files is working at all.


If my cursor is in the email's body, the image WILL attach inline, which is highly undesirable.


I just got settled in this app after being dissatisfied with all other Mac email clients. Now I can't even attach files???


Using app version 16.0 (3826.400.131.1.6), Sequoia 15.3.2 on a 2019 MBP. Any help is welcome.

MacBook Pro 16″, macOS 15.3

Posted on Apr 4, 2025 10:00 PM

Reply
Question marked as Top-ranking reply

Posted on Apr 7, 2025 5:54 PM

Re: Mac Mail Won't Attach Anything


Apple support's online article for MacOS 15 may help: Add attachments to emails in Mail on Mac - Apple Support

Eg: says:

"If the message size shown on the left side of the message header is red, the attachments are causing your message to exceed size limits set by your email account provider. Try reducing the number or size of

attachments, or use Mail Drop. See Send large attachments in Mail."

________________________________________________________________________________________________

Re: In the Mac Mail app, I'm trying to attach some PDFs and images to a draft and neither the paperclip icon nor File->Attach Files is working at all.


Above article says:"You can also drag files from the desktop, the Finder, or an app into your message".

Else:

If your Mac isn't working as expected:

(1)Try updating to the newest MacOS version: What's new in the updates for macOS Sequoia - Apple Support

MacOS 15.4 : "This release also includes other features, bug fixes, and security updates for your Mac."

(NB: please remember to back-up first if updating):

or

(2) Try restarting your Mac : ie: Apple menu > Restart (deletes temporary files, re-establishes connections, may update recent setting changes and often restores order.)

__________________________________________________________________________________

Re: "If my cursor is in the email's body, the image WILL attach inline, which is highly undesirable."


Apple Supports first linked article at the top of this discussion says:

"Send photos in emails

  1. Go to the Mail app on your Mac.
  2. Open the message you’re writing, then click in the toolbar.
  3. Drag a photo into your message.
  4. When you use Mail to send a Live Photo, the Live Photo is transferred as a still image only.

By default, Mail inserts images at their actual size. If different sizes are available, you can choose one from the pop-up menu located on the right side of the message header."


Also says:

_________________________________________

"Put email attachments at the end of messages

  1. Go to the Mail app on your Mac.
  2. Do one of the following:
    • 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 indicates it’s on)."

____________________________________________________________________________

Re: "I just got settled in this app after being dissatisfied with all other Mac email clients.

Now I can't even attach files???"


Understandable ... technology / software changes so rapidly and the learning-curve is not always easy to find or

climb. Else: if Apple Support's methods are still not working for you: You can send feedback to Apple. If others experience and make-known the same issue(s), we may see an update that addresses the problem-situation.

Web-form for : Feedback - Mail - Apple

________

Resource: Mail User Guide for Mac - Apple Support

__________________

Mail Support website: (info., support, contact options etc.) Mail - Official Apple Support

3 replies
Question marked as Top-ranking reply

Apr 7, 2025 5:54 PM in response to stevestate21

Re: Mac Mail Won't Attach Anything


Apple support's online article for MacOS 15 may help: Add attachments to emails in Mail on Mac - Apple Support

Eg: says:

"If the message size shown on the left side of the message header is red, the attachments are causing your message to exceed size limits set by your email account provider. Try reducing the number or size of

attachments, or use Mail Drop. See Send large attachments in Mail."

________________________________________________________________________________________________

Re: In the Mac Mail app, I'm trying to attach some PDFs and images to a draft and neither the paperclip icon nor File->Attach Files is working at all.


Above article says:"You can also drag files from the desktop, the Finder, or an app into your message".

Else:

If your Mac isn't working as expected:

(1)Try updating to the newest MacOS version: What's new in the updates for macOS Sequoia - Apple Support

MacOS 15.4 : "This release also includes other features, bug fixes, and security updates for your Mac."

(NB: please remember to back-up first if updating):

or

(2) Try restarting your Mac : ie: Apple menu > Restart (deletes temporary files, re-establishes connections, may update recent setting changes and often restores order.)

__________________________________________________________________________________

Re: "If my cursor is in the email's body, the image WILL attach inline, which is highly undesirable."


Apple Supports first linked article at the top of this discussion says:

"Send photos in emails

  1. Go to the Mail app on your Mac.
  2. Open the message you’re writing, then click in the toolbar.
  3. Drag a photo into your message.
  4. When you use Mail to send a Live Photo, the Live Photo is transferred as a still image only.

By default, Mail inserts images at their actual size. If different sizes are available, you can choose one from the pop-up menu located on the right side of the message header."


Also says:

_________________________________________

"Put email attachments at the end of messages

  1. Go to the Mail app on your Mac.
  2. Do one of the following:
    • 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 indicates it’s on)."

____________________________________________________________________________

Re: "I just got settled in this app after being dissatisfied with all other Mac email clients.

Now I can't even attach files???"


Understandable ... technology / software changes so rapidly and the learning-curve is not always easy to find or

climb. Else: if Apple Support's methods are still not working for you: You can send feedback to Apple. If others experience and make-known the same issue(s), we may see an update that addresses the problem-situation.

Web-form for : Feedback - Mail - Apple

________

Resource: Mail User Guide for Mac - Apple Support

__________________

Mail Support website: (info., support, contact options etc.) Mail - Official Apple Support

Apr 9, 2025 3:15 PM in response to stevestate21

Thank you for replying, and for letting us know you have tried adding attachments in the precise way the software is set up to work, yet without success.

_______________________________________________________________________

Re: I'm trying to attach some PDFs and images to a draft


A saved draft has to be active

(ie: not just open, but double click a saved draft in the list in a drafts folder for a copy to work on)

in order to attach anything (or edit / send).

More info: Save draft emails in Mail on Mac - Apple Support


The only other suggestion is to reach out to Apple's Mail Support Team (online chat / phone / email etc): There is a "Get support - start now" link at the bottom of their website (or you can download a support app.): Mail - Official Apple Support


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Mac Mail Won't Attach Anything

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