I've been reading this thread (and others) as I was having the same issues. I've tried all the suggestions regarding importing the certificates etc. and none of it worked fully. Sometimes I could get the account registered on my Pre but it would only show the Outbox as others have mentioned.
I decided to have a look on my Exchange server to see if anything was showing up in the Event Log and sure enough I found several Event ID 3029 entries with the following
The mailbox server [XXXXXX] has its [exchange] virtual directory set to require SSL. Exchange ActiveSync cannot access the server if SSL is set to be required. For information about how to correctly configure Exchange virtual directory settings, see Microsoft Knowledge Base article 817379, "Exchange ActiveSync and Outlook Mobile Access errors occur when SSL or forms-based authentication is required for Exchange Server 2003" (
Exchange ActiveSync and Outlook Mobile Access errors occur when SSL or forms-based authentication is required for Exchange Server 2003).
This took me to a Microsoft web page explaining how to set up a new virtual directory on the IIS server presenting OMA
Exchange ActiveSync and Outlook Mobile Access errors occur when SSL or forms-based authentication is required for Exchange Server 2003
I followed Method 2 on this page and now everything is working for me even with a self-signed certificate and with SSL still enabled on my main OWA site.
Hope this might help other people (although you will need access to the actual server or a friendly IT dept to sort it).
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