Mail.app SMTP issues following update

[doctor-frog]

Right. Updated from Kalyway 10.5.2 to 10.5.6 using netkas then, playing with my system, I managed to brick it and had to do a re-install from stratch. (Thank God for backups.) Since then, my SMTP in Mail.app has quirky issues that, whilst non-fatal, are very annoying.

 

I'm using Googlemail IMAP. When I restored my system, I transferred my mail files by dragging the two Mail folders in Users/{name}/Library/ from my backup to the active system. Then I cranked up Mail.app for the first time, entered my account info, and everything was there.

 

I quickly noticed, however, that if I leave it a long time before sending an outgoing email (which I usually do!), I often get a message, immediately after clicking 'send', that says Mail couldn't connect to the server at port 465 (or whatever), and would I like to try again, wait, re-send, or try a different server. The message also shows a list of servers that I've configured; sometimes one or more of these says '(Offline)' after its name; but this is by no means consistent.

 

It seems to me as if the message comes up even before Mail.app bothers actually to try connecting to the SMTP server -- although I may well be wrong about this. In any case, I almost never, only very rarely, have a problem when I click the 'Retry' button with the same server. Connection Doctor doesn't suggest any major problems connecting, either.

 

I think I've eliminated the firewall as an issue. (Although -- can anyone tell me in general: should I have the firewall configured to allow Mail.app to accept incoming traffic?)

 

I have also elimated Google as the culprit, since the problem does seem to happen to varying degrees with my ISP's smtp server, as well.

 

Anybody seen this one before?