Messages won't deliver JPEGs in Tahoe 26.2

Just tried it, copying and pasting the image (any image) on your desktop (for example) into the text message box. You have to right click on the image you want then paste it into the text message box in Messages. This problem started 2 days ago. I had updated to the Tahoe 26.2 and have the M1 chip on a MacBook Pro. Notice any picture that is really old, you have to hunt for it by date in your Library pictures on iphone. 💜 a pain, no fun. But at last this method works, was quicker and easier to drag and drop into the text message box but Tahoe 26.2 update took that away :-(

As has been suggested, copying and pasting the image into the text, rather than dragging it in, also seems to work. Wife having the same issue with her Macbook Pro since she upgraded to Tahoe 26.2.

Don't know why but it works but it does. Add 2 jpgs and

delete the extra one.

Copy and paste is a good workaround.

I had the same problem and found if I right click and convert to HEIF, I can drag and drop.

Same here. To send one image, have to attach two, then delete one.

I ended up dragging photos onto my Ipad from my Mac mini, and sending from there. Something's obviously broken in Tahoe 26.2! Will try the old copy/paste routine next time—thanks for the work-around.

same here. seems to be able to sent 2 jpgs at once .. not just one.

Helpful - thanks.

Steve J obs famous ly said of T im Coo k, "he's not a p roduct g uy". This is such a good example of the current downward trend of the Apple operating system software for the mac.