another_silly_human wrote:
Hi, I am getting this message when i try to send an email that has any attachment on it.
I have a couple of signatures with attachments also and they bring up the same problem.
If I add the attachments manually it seems to work but now even replying to a message that has a logo attached wont send. Seems to be since the last update. Please help its getting very problematic and cant seem to find any recent posts of the same problem with any answers that work.
Have not heard this issue before.
It is the courteous thing to strip off all old attachment... before replying yes,
but it does not account for your problem.
Where are these attachments, compared to when you say "If I add the attachments manually it seems to work."
—Look at your Mail>Settings>Compose>Responding and make some changes here and test, then come back to your preferred settings and compare your results.
—also I would try turning off any delay option as a test.

Can you verify your software is up to date…
The current stable release of Ventura including bug fixes, security updates is macOS Ventura 13.2.1
Keep your Mac up to date - Apple Support
Keep your Mac up to date - Apple Support
if no resolve verify Mail.app has Full Disk Acess

ref: Mail User Guide for Mac - Apple Support