Does this happen on any network or just specific networks?
Such timeouts can appear depending on the proxy configuration and/or multi-NAT setup. E.g., one of our campuses is connected through one IP, thus all traffic is routed through a squid proxy. If squid has a hickup, K-9’s connection times out rather than detecting the network hickup.
I have not tried on any network, other than my home network, but I will have an opportunity this morning to try another. I’ll let you know if I see any failures. Since the timeout is intermittent, this may not be an adequate test.
I have the same issue, except it affects ALL of my sent email. They all end up in my Outbox folder. When they finally timeout with that error all I do is choose “send messages” and it works. This happens on my LAN (local dovecot imap) or when I’m remote over the Internet. Ie always fails first time but works on manual retry. Other IMAP clients don’t have this issue