Screenshots not sending from Mac via Messages

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Level 1

12 points

Screenshots not sending from Mac via Messages

I am having a new issue sending screenshots, captured as png images, via Messages from my Mac. The messages are marked "Not Delivered." Through testing, I have determined that the issue is not dependent on the recipient, the type of screenshot (i.e. a portion of the screen, a specific window, or the entire screen), or the name of the screenshot. If I Airdrop the image to my iPhone, I can send it normally from my iPhone, but if I then download that same file from Messages to my Mac, it still will not send from my Mac. The file will send from my Mac if I first import the image to Photos. If I convert the file to a jpg or other file type, it also will send.

Posted on Dec 31, 2025 10:03 AM

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Answer 1

brbo

Level 8

38,713 points

Jan 6, 2026 9:46 PM in response to JHZJ

Re: Screenshots not sending from Mac via Messages

We do not know which Mac model (year) you use for Messages, and which MacOS version is installed.

or

whether you are using wi-fi (iMessages: blue bubbles) or cellular data (texts: green bubbles)

when sending screenshots leaves them undelivered.

You might want to try making the screenshot without saving it as a png,

Either click the "share" button at the top of the screenshot, choose Messages recipient:

Or

You can "copy" the screenshot and "paste" it into the message field in a message window.

Add a written message or not, and send.

If you wish to keep it safely: remember to then "save" the screenshot

____________________________________________________________

Re: The file will send from my Mac if I first import the image to Photos.

Messages may need to "save" the screenshot to the recipient's "Shared with You" folder (default setting)

in the Photos app. Sending from Photos may expedite that process.

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Answer 2

brbo

Level 8

38,713 points

Jan 7, 2026 5:54 PM in response to JHZJ

Thank you kindly for your reply and info.; interesting to note you prefer your own workaround.

You may want to send feedback to reach those who work on the software behind-the-scenes at Apple. (You could include a link to this discussion thread if you wish.)

Your feedback will be carefully read and logged, and if others have a similar issue we may see it addressed in a future update.

Web-form for feedback: Feedback - Messages - Apple

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Answer 3

JHZJ Author

Level 1

12 points

Jan 7, 2026 5:46 AM in response to brbo

Thanks for the reply. Here's some more information:

MacBook Pro, 2023

Tahoe 26.2

All messages, iMessage or SMS, have the same issue.

As I mentioned in my description, I have already found a work-around. I can simply convert the images to jpg, and then they send just fine. However, this is a new issue, i.e., screenshot sending worked fine in the past. I'm reaching out to the community to find a way to restore correct functionality. By "correct functionality" I mean I can send screenshots from my Mac that are generated using the shortcut ⌘ + Shift + [3 or 4 or 5].

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