So you want to jump into old Windows? Fasten your seatbelt, as you might not be ready for what it takes.

Obviously, if you live in 2026, the best way to get old Windows running is a virtual machine. Modern hardware supports usually only Windows 10 and 11.

When in doubt, go NT. Windows 9x is terrible on new processors, as after some Spectre / Meltdown mitigations it just keeps BSoDing even on VMs. I think Intel 10th or 11th gen was the first one to go quirky ¹⁾. On AMD anything marked with Ryzen is probably also a sudden death scenario ²⁾. If you are on those processors, forget KVM, forget hardware-accelerated virt. It will yield you nothing, unless I do not know something yet.

Somehow, Me was the least quirky during testing on a Ryzen 4000-series mobile CPU - it got through the install, at least it boots, but it's still unbearable. I cannot stress it enough - when in doubt, go NT.

If you really need 9x in a box on modern hardware, the way to go is 86box / PCem and trying to set up a virtual PC fast enough to not make you commit crimes.

If you're somehow still on Windows 7, great news! Virtual PC 2007 is the king there, and it works flawlessly. Otherwise, you can get some success on VMware. But only if you are not on a said cursed processor. Skylake / Kaby Lake works fine tho.

Generally Windows 9x was not a great product anyway, with no proper isolation of processes and BSoDs when you looked at it the wrong way. NT maybe wasn't the great choice for games and NT 4 was not particularly friendly, but usually this is what you want to not get yourself a blister on your thumb ³⁾. Really. when in doubt, go NT.

This is where it gets fun. Some Windows versions where actually supported much longer than you think on the side of hardware, and maybe you can get some relatively new box run the Windows version you want.

You are officially supported on Intel side until Ivy Bridge series of processors, including integrated graphics. Although the drivers start to get quirky - but you can run it natively with minimal effort.

It is said that Haswell-based systems have unofficial, ported, leaked or whatever drivers for XP. Never tested, YMMV.

If you want to be closer to the golden age, go for Core 2 series, preferably the Wolfdale-based designs. They also run Vista, 7, 8, 8.1 and early 10 like a breeze.

On AMD side of things, you are fine until the Bulldozer series - so all the AMD FX processors and Am3+ CPUs will run XP like a breeze - but this is heavy overkill territory.

Intel did a nice gift to us. You can run Core 2 Duo natively with Windows 2000, although you need a specific chipset, and mostly only 1st gen Core 2 (Conroe / Arrendale / whatever) runs fine.

If you want, Intel 945G / Intel 965G chipsets are really a good bet. You get chipset drivers, and you can get official drivers for those terrible GMA integrated graphics.

AMD side of things still to be confirmed.

Get it updated. Usually RTMs will not get you very far. If you do not want to update them to the brim, at least get latest available Service Pack and Internet Explorer - you will thank yourself later. Many pieces of software expect later binaries and APIs provided by them. There are some quirks which I will explain below

Vista was terrible in its early days. Get a service pack NOW. SP1 is serviceable, SP2 is better. Better yet, just get a SP2 image.

It is a good idea to update Vista to the brim. Get Legacy Update. On Vista, it allows you to update either through the website, or through the control panel (wuapp). Choose what you prefer, for Vista I prefer wuapp.

Despite the rumors of Vista being a flaming dumpster, it is rather forgiving and pleasant to get running and use. There is no concept of updates that need to be installed separately in Vista, everything clicks in. You get a lot of concepts that appear in later versions of Windows. It really might be what you are looking for, if you know its limitations.

XP service packs are… interesting. You got 4 - SP1, SP1a, SP2 and SP3. To get going, you need at least SP1 - many apps expect at least some kind of service pack. SP1a was almost the same as SP1, but without Microsoft's Java VM fiasco - when I say about SP1 in this section, this applies to SP1a too.

This is when it gets quirky. SP2 was not just a service pack, it did a really large overhaul underneath. XP SP2 is a completely different OS underneath than SP1. Many security popups changed to Vista-style ones, some old applications are no longer available (like progman and winfile), and, the lamest… bootscreen changes, from distinct ones for each edition to an unified one. I was personally not able to switch it back to the old one. Keep this in mind if you want to play around. SP2 mostly strips Active Desktop as well - on SP1 most of the toggles are still there, on SP2 there are gone - don't know why. Also, for whatever reason, on SP2 you cannot put the Internet Explorer icon on the desktop, unless you enable classic start menu - then it forces you to have IE icon on desktop. Dumb pattern.

Also note that one of the service packs bumped up Movie Maker to a newer, fancy version. If you wanna use the OG Movie Maker, probably SP1 or god forbid RTM might be the way to go for you.

If you update to IE7 or IE8, you lose the ability to use Explorer to browse the Internet, and it shamelessly opens a new IE window. It detaches IE and Explorer, although I bet some parts of IE6 are still under the hood to keep this shell working.

Updates are quirky on XP, sometimes they go through like a breeze, sometimes you might be left with a half-baked OS with random stuff broken - I haven't found out why yet. Although you need some updates after SP3 to get fully updated Office 2010 working. Anyway - it's better to be updated to the brim, but you might wanna take a snapshot of your drive before you begin. Updates can be performed with Legacy Update.

Another approach is to bake yourself a custom ISO with all the updates built in. nLite is your friend.

Generally, despite all of this, it is a good idea to have fully updated XP with SP3 and IE8.

NT 4 is not really usable if you don't have SP6 or SP6a at all. Get SP6a as soon as possible - it allows you to use drives larger than 8GB, install VirtualBox additions (or whatever) and just use the computer.

By default NT 4 comes with a Windows 95-style Explorer, which might seem too simplistic to some people (I like it though). If you do want a more Windows 98-like desktop, with Active Desktop (might be helpful sometimes) and newer configuration windows, install IE4 with its Desktop Update. If you want to have the newer shell, it is imperative to install IE4 before you upgrade IE again as you will not have a chance to do it again. Make sure to skip RealPlayer install with IE as it will probably be stuck for an hour or so. If you want the new shell and the installer does not prompt you to install Desktop Update, stop right now and look for a different IE4 install.

After that, install IE6 SP1 normally. It won't break anything, except the immersion, as IE6 has the XP icon.

NT 4 is quirky. It will never ACPI shutdown by itself always tell you to turn off your computer by yourself, no matter how much you try. Just give up and live with it. Drivers are managed old-style, there is no Device Manager - this is a 2000 addition. MMC is installable, but not sure how much it will help you. Audio drivers are installed manually - SB16 usually works, might need a bit of tinkering. If you're bringing your own driver, YMMV.

Windows NT 4 is updateable online using Windows Update Restored, using Windows Update 3. You will never get Windows Update 4 working unfortunately, but you get a retro look instead.