If Outlook Express has stopped connecting to your incoming mail servers, try logging out of OS X and logging back in. Worked for me.
Basically I had to switch to a PPP connection for a few days (from DSL) and Outlook Express didn't like that. Nor did it like it when I came home and switched back to my DSL connection.
I don't know why logging out and logging in worked when clicking "Apply Now" and even restarts didn't.
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Mac OS X Hints
http://hints.macworld.com/article.php?story=20011120122147300