I've seen this problem crop up quite a bit now that most of our users have been upgraded to Outlook 2013. We have quite a few remote users, who generally use VPN's to connect to our network, but they shouldn't have to use a VPN since we run Outlook Anywhere.
The problem is: when running Outlook 2013 in Online Mode, they get a "Cannot open Outlook, or cannot expand folders..." error, during start-up. I believe it has to do with the way Outlook 2013 processes certificates, but I'm not sure what causes it.
Here's a workaround that seems to work pretty well:
Since you probably can't open Outlook, go to Control Panel > Mail > E-mail Accounts
Select your account, then click “Change...”
Click the “More Settings” button
Select the Connection Tab > Click the “Exchange Proxy Settings” button
Delete the entry in the box under “Only connect to proxy servers…”
Uncheck the box next to “Only connect to proxy servers…”
Click OK, OK, Next, and then Finish.
You'll be prompted to close and Restart Outlook, after which, you should be able to connect to Exchange using Outlook Anywhere.
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