Syncing is a bit more sophisticated than importing a mailbox to Outlook as syncing implies you will not import previously copied messages with subsequent sync activity. However, if you are careful to move the already imported messages from the Entourage folder you're using for copying (say, blackberry) you can avoid duplicates. Not that dups are that big a deal. Anyway, you may be able to directly import the Entourage blackberry folder (or what ever you call it) into Outlook.
Entourage uses a standard mbox storage format for mail as does Mozilla/Thunderbird/Netscape, and Outlook (Express) can import files from these mail readers. So you might try copying some mail boxes over to a folder in Windows or one on your Mac that Windows can see, and attempt to import the mail using Outlook's import tool.
To be on the safe side, be sure Entourage is off when you do the copy so that it won't receive new mail while you're experimenting.
I've not tried this, so buyer beware. Outlook may be unable to browse in locations you provide, but rather may look for an installation of Thunderbird or whatever and look there. If that is the case it may be necessary to have a Thunderbird installation in your Windows environment.
Another way, and I think an easier way because I run imap servers, is to simply copy the Entourage mbox file of interest to the imap server spool directory, giving it your login name, and then you simply grab the messages using imap in Outlook. It requires shell access or ftp access to a server with imap services.
Better of course would be to have direct Blackberry support in the Windows VM. What problem did you have with that?
Last edited: Mar 17, 2007