Can't drag images into text messages

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Level 1

37 points

Can't drag images into text messages

Hello Mac people, this problem started yesterday. I am on my Macbook Pro all day every day, and I didn't make any changes that I know of. OS is up to date - Tahoe 26.2. Wifi is excellent.

When I drag an image (jpg, png, heic) into an iMessage, I get a box with the filename instead of the image, and it says "error - not delivered, message failed to send". Text-only messages are no problem. I tried restarting and shutting down, but no change. What to do????

MacBook Pro 16″, macOS 26.2

Posted on Dec 23, 2025 1:56 PM

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Answer 1

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rayredure40 Author

Level 1

37 points

Dec 30, 2025 3:07 PM in response to rayredure40

Update - it’s not me, it’s not you, it’s our friends at Apple. This is a known bug with OS 26.2. There are some work-arounds until Apple releases a new OS. Drag more than one image into the message, and it works fine.

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Answer 2

rayredure40 Author

Level 1

37 points

Dec 30, 2025 3:09 PM in response to G J Piper

Evidently, this is a known bug with OS 26.2. There is a work-around until Apple releases a new OS. Drag more than one image into the message, and it works fine. Found that out by accident.

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Answer 3

G J Piper

Level 1

112 points

Dec 29, 2025 3:52 PM in response to rayredure40

ME TOO with Workaround!

I have this problem too. Sending to verified apple users with blue names. I can't drag a jpg into the message box and send to some of my apple contacts — only some of them. Others it works fine. If I right-click on the image file and select "copy" then paste it into the message box it works fine... just can't drag it in there anymore.

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Answer 4

Dec 23, 2025 4:14 PM in response to rayredure40

Are you sending to an Apple user? (blue) or a brand-X user (green) ?

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Answer 5

rayredure40 Author

Level 1

37 points

Dec 23, 2025 4:31 PM in response to Grant Bennet-Alder

I am sending to an Apple user.

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