Cant send Attachments

Its been about a year since I’ve suddenly had an issue where any email.i send gets stuck in my outbox. Tried from wifi and cell and even as small as 300k files. Sometimes running synchronize account gets it through, but not everytime. I tested using Gmail client and it works everytime..

The error message isn’t completely clear due to my screen resolution but it says basically cannot send message

I have this problem also, but only when attaching the file to a reply.

It will not send (not on repeated attempts, either) until you edit the mail from outgoing as a new mail and try again.

I run K-9 version 20.1.