After configuring Outlook 2011 (Mac) to access two IMAP accounts hosted by my hosting provider (Dreamhost) AND Outlook is able to access the account,, after a little while I will constantly get notified with the following:

The server for account "<account name>" returned the error "Logon failure: unknown user name or bad password." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

It turns out that Outlook is disabling the authentication settings on the outgoing server - changing my setting from 'Use Incoming Server Info' to 'None'.

I seriously doubt this is a Mac problem seeing as how the Outlook account configuration is an Outlook responsibility.

Once I corrected the changes,  the messages stop. However, they do reappear from time to time.

I know Outlook is a 'champ' with Exchange, but this kind of carelessness, on the part of Microsoft, is a reminder of whom Microsoft is looking after and it isn't the consumer.

Has anyone else seen this behavior?