Messages not sending images after macOS 26.2

I encountered this problem while trying to send photos from a folder on the desktop. It was baffling. I found this discussion and tried dragging multiple photos to Messages, and yes, it worked. One of the responses here says it only seems to happen on the desktop, so I moved my folder to the Downloads folder and tried from there. It had the same problem.

However, most of the time I use Path Finder, so I tried dragging a photo from the folder in Path Finder to Messages and it worked fine.

Then I moved the folder to the desktop, dragged a photo from it using Path Finder into Messages, and it worked again.

I dragged one photo to the desktop and tried dragging directly from the desktop to Messages, and as expected, it exhibited the problem. I dragged the file from the desktop using Path Finder to Messages, and it worked.

Searching a bit more with the info in this discussion shows that this is a known bug in the Finder.

Geez louise. Confirmed unable to send .jpg images via drag and drop on Messages, for these machines all running MacOS 26.2 on M4 mini, M2 mini, & 2019 MacBook Pro. Copy/paste workaround is inelegant but it does work. No issues with drag & drop with .tif, .png, .gif, .pict, .bmp, .psd or even .heic images. All work with drag & drop.

Seems to be .jpg or .jpeg suffix that causes the drag and drop issue. Most all of the other file suffixes I tested were okay on the drag and drop. I changed a .HEIC file that worked to a .jpg name and it failed. Changed it back to .HEIC and it worked. Using MacBook Air and Tahoe 26.2

Same problem here on 2.6.2. Single image not showing, and can't be delivered. OK for more than one image. No change if it comes from the desktop or another folder. I created a test session, and it works fine. But I don't want to be forced to transfer all my files and settings from one session to another ! I hope the bug gets fixed soon. Macbook Pro M5.

I also noticed that dragging two or more images works fine for me. It's just a single image, dragged from desktop that is the issue.

Correction, it's not a Finder bug, but a bug with the way Messages handles drag-and-drop from the Finder.

I was just coming to ask the same question. I hope Apple comes up with a fix soon.

Same problem here and noticed it immediately after updating to 26.2.

For me, this bug happens when dragging images specifically from the desktop. If the image originates in another folder (say, Downloads), the bug does not happen and images load normally.

Like another poster said, copy/paste is my current workaround for images originating on the desktop.

It also happened with a simple bit of text typed into the Messages field where I then dragged a png from desktop into the field. But earlier the text part had been sent and the png failed, so the recipient gets a confusing text.

I just read about and tried, copy and paste. It works. Use that instead of or until drag and drop gets fixed.