Only if you use one of the allowed big email services. Set up your own and you might be secretly black holed and your emails will randomly not reach the intended recipients.
... and not just self hosters: ProtonMail has had to fight Microsoft and Google on this for years.
(Looks like the hotel me and my son are traveling to in three weeks haven't received photocopies of our documentation either through Booking's internal email system or to their Gmail. I'm sending through ProtonMail, and my _guess_ is that it's due to the large size of the attachments. No errors returned ...)
@troed @philleu @rolle @Daojoan I have a (rarely-used) Proton Mail account, and have do not recall ever having issues emailing Gmail or MS account, but I’ll certainly test it.
If you’re sending something over the file size limit, you should get an error notification, but not always (some servers just silently fail, which is annoying).