Raspberry Pi Emulation Windows 2000 for ActiveSync

Hi, I have a Raspberry Pi Model 1B with 512MB RAM.

I couldn't really find a straight answer when I looked online, but I was looking to emulate Windows 2000 for ActiveSync usage with either my USB->Serial or my USB->IrDA adapters.

I know Windows 2000 will be slowwwwwwwwwwwwwwwwwwwwwwwww on the Pi 1, but it just needs to be good enough to run Outlook 98 + ActiveSync 3.8 + Windows 2000, even if at a crawl.

Which program should I use? I have Debian Buster currently (the Pi OS variant), but I could upgrade to Bullseye, or downgrade to an earlier Debian if it's recommended.

Here's a video I found on YouTube: (I think it's running on Raspberry Pi 1)

According to the description of the video, it takes an hour to boot...

You can use qemu to emulate i386.

Raspberry Pi 4 running Windows 2000 on a docker environment.


Edited by stingraze 2022-10-10 7:41 AM

I wouldn't use 2000. Try and get 95 working as it will run all the stated software much, much lighter than NT ever will. If you can get DOS box working it may cope.

Thank you both! I was trying to find uses for my Pi1, since it's soooo old. I think I'll turn that one into my repeater for WPA1/WEP.

I have a Pi4, so maybe I'll rig Windows 2000 on that one. My Pi 4 has 8GB of RAM

Even on the Pi 4, it'll be super slow. I can barely do Windows 95 in PCem on my Pi 4. I can do something like a 16MHz 486 (which is a very low clock rate for a 486).

Edited by null1024 2022-10-10 10:29 PM