Spent 4 hours last Saturday getting a 1996 PalmPilot to talk to my Windows 11 PC
I found my dad's old PalmPilot III in a box of stuff from his garage in Phoenix, and of course the battery was long gone. I ordered a new one for $14, soldered it in, and the thing actually booted up to the 1996 date screen, which was a great moment. Then came the hard part, because the serial cradle needs a real 9 pin port and my new tower has zero of them. I went through two USB to serial adapters and a driver from a forum post before I found out the trick was running the old Palm Desktop software in compatibility mode for Windows 98. Anyone got a better method for syncing these old organizers, because I am not doing that every time.
That Windows 98 compatibility mode trick is the standard fix and honestly I don't think there's a cleaner way with the old serial cradles. I went down this same road with a Handspring Visor two years ago and tried a PCIe serial card, a FTDI adapter, and a no name China adapter, and all three had flaky handshaking until I just gave up and ran Palm Desktop in a Windows XP virtual machine. The VM route sounds like more work but it only took me about 30 minutes to set up once and now every sync just works. You can also drop the cradle completely if you get a USB sync cable for the III, they make them with the chip built in and skip the serial mess altogether. Four hours for one sync is rough but at least that battery solder job held up.