Messages not sending images after macOS 26.2

Ever since I have upgraded my software to MacOS 26.2, the Messages app will not allow me to send attached pictures (JPG, PNG) (drag drop) as usual, and the new picture icon is blank as well. Prior pictures above the prepared message show up as normal. Yes, I have deleted the Messages and iChat preference files, signed out and back in with my Apple ID, restarted the computer and program, checked the internet and wifi connections, and have sent text files, without attachments, successfully via the app. I made sure that my iPhone 17 Pro and M4 iMac are synced and iCloud connected. I also pay for additional iCloud storage. There is a glitch somewhere.


Please help,

Jerry P.





iMac 24″, macOS 26.2

Posted on Dec 15, 2025 4:43 PM

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Messages not sending images after macOS 26.2

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