I have the following problem with Outlook. I have an IMAP account configured with SMTP with SSL authentication (it is using a self-signed certificate, so a warning window must be checked everytime SMTP is used for first time in a running Outlook).
The most strange thing that occured is that certain email addresses won't generate any action on the SMTP server, but Outlook reports no error and states the message has been successfully sent. In SMTP server log, I see this and this only for the message:
Sep 27 10:10:58 edna qsmtpd: auth ok for login: email@example.com
And of course, as no further action is taken and email is not sent physically.
This happens to two email addresses, for anything else SMTP functions perfectly. I had no problems with the same SMTP in Outlook 2007. These One of them is in the same domain as my email, one is not.
SMTP config is: AUTH type plain, requires login & login same as incoming.
Any help is appreciated.