“Your message could not be sent” Error on Attachments Only

[pjkelnhofer]

I recently started getting the error:

Your message could not be sent.
There was an error sending the previous message. Would you like to try to send it again?​

It is when I sent anything with media from messages on my iPhone and then I start using my MacBook Pro. The text only messages work just fine, but images are not syncing to my MacBook. I just get the bubble with the name (something like "IMG_9765.jpg"). It has the download arrow (which does nothing) and the red alert exclamation point. But trying to manual download the images also doesn't work.

This is true of images I send and images I receive from others. Until about a week ago, images synced just fine between devices. I looked through multiple forums and the fixes for iMessage not syncing (logging out on all devices, restarting, signing back in) have made no difference.

Any ideas?

 

[gsahli]

You should look into whether your internet provider/email service is restricting the size of emails.

 

[KoolAid-Drink]

You should look into whether your internet provider/email service is restricting the size of emails.

I believe he was referring to iMessages, not emails, which is a separate thing.