You're going to need and usb to serial adaptor. I got one from keyspan, the 230Kps. You don't need to get this fast one because the Pocket PC only seems to connect at 115Kps, but if your go with the 230Kps you'll need to download the driver from keyspan. Also you'll need MS ActiveSync 3.1. Be sure to install the driver on the Mac OS and don't bother with installing it onto the VPC windows. I am using VPC4 w/win98. I have a iPAQ 3650 running a GIS software called ArcPad which I use to connect with a Trimble GPS unit, then I connect to the VPC and download the information to ArcView, another GIS software package. This is real world application using VPC. When I first started looking into this I wasn't sure if I could do this, I posted here and several other boards. At the time someone responed and said that Connectix was going to add support for Pocket PC's in the next release of VPC. I should have mentioned this, you cannot use USB, this is what Connectix is working on, providing support for USB Pocket PC devices. Good luck and just know that this will work. Personally I will upgrade to the VPC so I can use the USB connection, it's so much faster and I often have large files I need to transfer back and forth.