Ok, bear with me, as this one is a tad convoluted The Problem: Blackberry won't sync well w/ Outlook inside the Parallels virtual machine. The USB support is flaky at best, and I can't seem to make it work consistently. Plus it's a pain to constantly fiddle w/ the virtual connection. The (sort of) Solution: PocketMac is available for free, and syncs fantastically with iCal (and AddressBook, but that is something to tackle later...). But wait...iCal isn't Outlook! Richard, you are crazy! Keep reading How it works: Outlook can be made to export your calendar to iCalendar format, via a number of ways, but the best one I found was this script called (amazingly) outlook2ical.js from Ryan Watkins (http://www.ryanwatkins.net/software/ ). This script will (at default) output a file called c:\calender.ics. Using the standard scheduling and ftp commands inside of Windows, and the FTP server and iCal features in OS X, you can automatically get that file published to iCal in OS X and then easily sync natively with Pocketmac. Now, the steps: 1. Enable the FTP capabilities in Sharing pane in OS X. 2. Download the outlook2ical script, and put it somewhere in your Windows virtual machine 3. Write a txt file that contains the commands needed to ftp the file over to OS X. This file will be read in by the ftp program using the -s:scriptname parameter. (see "samplescript.txt" below) 4. Write a batch file that runs the outlook2ical script, and then calls ftp to move the file (see "putcal.bat" below) 5. Use Scheduled Tasks to run the putcal.bat as often as you see fit. 6. Subscribe iCal to the calender.ics file in your ftp location with this url: "ftp://localhost/calendar.ics". Then set iCal to update it as often as you see fit. 7. Install PocketMac and set it to sync with iCal on connection. Code listings: "samplescript.txt" open 172.25.2.2 <-- note that this is MY Mac IP, you need to put yours here (and read below) put_your_username_here put_your_password_here binary put c:\calender.ics quit "putcal.bat" c:\outlook2ical.js ftp -s:samplescript.txt Now, a wise man can also see that this could work for BootCamp users to SOME extent, if you had some kind of startup script in OS X that would go grab the calender.ics off the Windows partition and put it into the proper FTP location. However, it would be infrequently updated at best, and if you're using BootCamp, why not just sync under Windows I did try using RemoteCalendars first, but this method has some issues: * You have to setup WebDAV on your OS X box, which can be a little tricky * There doesn't seem to be a way to automate the update of the publishing of the Outlook calendar to the WebDAV share (I had to click it manually every time). At any rate, this seems like it will work, but of course any time my Wifi IP (172.25.2.2) changes, things are going to break. Perhaps some kind soul can help me figure out a way to address my OS X by hostname to get around this? Comments and suggestions are heartily welcomed (also posted on my blog at http://www.richardgoodwin.com/wp/20...look-inside-of-the-parallels-virtual-machine/