Messages won't send to one recipient
Though I successfully message back and forth with my friend from my iPhone, I keep getting error message "Your message was not sent. Click Try Again to send this message." when I use the Messages desktop app.''
I've tried the following:
- rebooting the app and the OS
- making sure I'm logged in on the app
- messaging others successfully with the app
- enabling all essential preferences
What could be the reason for my desktop messages not going through for 3 weeks?
MacBook Pro 15″, macOS 12.6