Messages aren’t being sent

If you click the red error bubble next to a failed message, you’ll see an error message. Please take a look at the explanations for each error message:

Couldn’t connect to AirMessage Server

Your phone is disconnected from the your server. Check your network conditions or your connection setup.

Request timed out

Your phone is having trouble communicating with your server. Check your network conditions or try again later.

Couldn’t connect to iMessage server

Your message was successfully delivered to AirMessage Server, but couldn’t be passed on to iMessage. Please check your Mac computer’s network connection, or check Apple’s status page for outages.

The recipient is not registered with iMessage

The contact address you are trying to send a message to is not registered with iMessage, so the message could not be sent.

AirMessage Server isn’t allowed to send messages

AirMessage Server requires automation access to request messages to be sent, and this permission has not been granted. On your Mac, navigate to System Preferences > Security & Privacy > Privacy > Automation, and enable AirMessage.

This conversation isn’t available on the server

A matching conversation couldn’t be found to send a message to. Perhaps this conversation is from an old connection? Delete this conversation and create a new one.

The selected content is too large to send

The file you are trying to send is too large. Please select a smaller file.

Couldn’t process selected content / The selected content is unavailable

There was a problem preparing the selected file for upload. Please try reselecting the file.

An internal error occurred

There was a problem preparing the selected message for upload. Please try again.