If you encounter this error:
"Cannot open your default e-mail folders. You must connect to Microsoft Exchange with the current profile before you can synchronize your folders with your offline folder file."
Shut down Outlook and add a "wininet" key to "HKEY_CURRENT_USER/Software/Wine" of the bottle's registry. Then add a DWORD value to that "wininet" key. Name the DWORD value "accept_invalid_certs" and set it to "1".
Instructions on adding a registry key can be found here:
For Mac
For Linux
Why did this happen?
Outlook 2010 has stricter security settings than Outlook 2007 and earlier, and by default won't connect to an Exchange server that is using a self-signed security certificate. Self-signed certificates can be created by administrators and will setup a working SSL connection, but aren't signed by an official Certificate Authority (like Verisign) and since Outlook 2010 can't verify the authenticity of the self-signed cert it rejects the connection.
You can tell Outlook 2010 to bypass this check and connect to the Exchange server regardless by editing the registry of the bottle containing Outlook.
This setting affects connection security; don't use it unless being really sure your certificate is not trusted and it is intended to be this way.
Signing with corporate CA may be, however, more tricky.
Another possible cause for this error is that Outlook cannot resolve the IP address of your email server. Try adding the IP address and local name of your exchange server to your /etc/hosts file, i.e.
123.123.123.123 email.exchange.local
Jack Phinney on 2013-09-26 16:17:30
