Having got Windows XP and Windows Vista working in VMs, with Windows Update working for both, and with each participating in robust network file and print activity, I was keen to find out how far back I could go back with legacy Windows operating systems before I perceived there were more disadvantages rather than advantages in doing so. Next stop, Windows 95.
Installation of Windows 95 into a VM was straightforward. I found this article a good starting point, though I ignored most of the advice, given I was working with a VM rather than installing Windows 95 directly onto modern hardware. I struggled setting up network file and print services. It is still possible to set up file services, at a cost of weakening network security. Refer to my previous post for details.
Forget about print services. It is virtually impossible to buy a new printer compatible with Windows 95. The Windows 95 market share is too small for printer manufacturers to bother providing drivers for the platform. It may be possible to buy a secondhand printer off eBay, but given the vintage of these devices and the fact that printers have many moving parts, there’s a good chance you’ll be buying someone else’s mechanical issues.
As for Windows Update (WU), all my attempts at getting this working on Windows 95 have led nowhere. Microsoft state that Windows 95 is unsupported, but I haven’t come across a definitive statement from Microsoft to say WU doesn’t work. After all, Microsoft also states that Windows 2000 is unsupported, but with a little help from Windows 2000 enthusiasts, WU, to this day, still works in Windows 2000. There isn’t any recent evidence though, that I’ve seen, of anyone successfully getting WU working in Windows 95. The most recent time seems to be in this YouTube video from 2009. There is also some sketchy evidence to suggest it was still working up until around 2012. WU in Windows 95 has become the Loch Ness Monster of Windows. There have been some sightings, and there is still hope that it will be seen again sometime.
Microsoft ceased supporting Windows 95 in 2001, so it’s a bit of a stretch to expect too much from this operating system today. With the file and print issues, and Windows Update issues identified, my journey back in time to earlier Windows systems stops with Windows 95. I won’t, for instance, be pursuing setting up Windows for Workgroups 3.11 in a VM. The further back I go, the more challenges and issues I’m likely to find.
Windows 95 is now on life support. It may be time to pull the plug and let it slip away quietly.
Edit: Sometime later, I found a way to set up file services without weakening network security. Refer to the post Stronger Authentication for Windows 95.