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timppu: - 16bit programs wouldn't work (unless Windows 7 is the 32bit version?). Like some old Windows games installers were 16bit, even if the game itself was 32bit. So you had to find some other way to install the game manually, copying files etc., or find a user-made installer for the said game.
Or you could use otvdm.
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Darvond: I can only hope your machine is airgapped. Personally, I'd rather just drop in Linux and run Wine, then trying to deal with a 20 year old OS.
I'm also more interested in finding ways to run the old games in modern OSes (running on modern PCs), if not for those old machines eventually dying at some point, there's just no way around that. Like dgVoodoo is quite often the lifesaver in modern Windows machines (the latest being that it can now ever fix the physics problems of Interstate'76, by being able to limit the framerate to e.g. 20 fps or so).

And yeah, Linux seems to be becoming more and more the place for running older Windows games, with Wine and such. I am becoming more and more comfortable trying to get old Windows games to run on Linux, instead of modern Windows PCs. It just seems Microsoft breaks lots of backwards compatibility with each new Windows version they come up with (sometimes even with new updates within the current Windows version), it seems to me in Linux that happens less, or is more predictable, or there are ways to get past it.

At this point, the main reason for me to keep a few retro-PCs with old Windows versions, are certain CD-based PC games with copy protections. It would of course better to just try to find working no-CD cracks for those and try to run them on modern machines instead...
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timppu: - Windows 7, or actually Windows Vista, introduced the "rainbow color problem" that many older Windows games had in Vista/7. There were various ways to work around that though, like killing the explorer/Aero/whatever before you launched the game.
Posting this here for the benefit of those unaware but W7 DirectDraw Compatibility Tool and similar tools long eliminated the need to taskkill explorer.exe before play vs the "rainbow colour bug". All they do is enable a registry flag (per game) that enables W7's built-in fix. I have original Age of Empires 1-2, Diablo 2, etc, running as well on W7 as on XP "natively" (without the need for any wrappers).

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timppu: - At some point, certain CD-based copy protection schemes stopped working in Windows 7 (and later). However, in Windows 7 it was possible to enable the parts that were needed by the copy protection schemes. In Windows 10 it wasn't, AFAIK. Or then you try to find working no-CD cracks for those games, if it allows them to run in Windows 7 (and later).
Indeed. One of the sanest things I did though was to source a NoCD immediately upon buying every disc based game that had any DRM. No DRM = no W7-10 issues at all. Quite a few games have also had it officially removed in later patches (Diablo 2, Neverwinter Nights DE, Operation Flashpoint Cold War Crisis, Prey (2006), etc) or side-stepped via source ports. It's been so smooth I genuinely forgot half these titles were originally DRM'd in the first place.
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timppu: - Windows 7, or actually Windows Vista, introduced the "rainbow color problem" that many older Windows games had in Vista/7. There were various ways to work around that though, like killing the explorer/Aero/whatever before you launched the game.
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AB2012: Posting this here for the benefit of those unaware but [url=https://www.pcgamingwiki.com/wiki/Glossary:DirectX/DirectDraw_troubleshooting]W7 DirectDraw Compatibility Tool[/url] and similar tools long eliminated the need to taskkill explorer.exe before play vs the "rainbow colour bug". All they do is enable a registry flag (per game) that enables W7's built-in fix. I have original Age of Empires 1-2, Diablo 2, etc, running as well on W7 as on XP "natively" (without the need for any wrappers).
Yeah there are several ways to fix that, but I am unsure I'd tell a casual user to go edit the registry. Probably would have to do it myself for them.

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AB2012: Indeed. One of the sanest things I did though was to source a NoCD immediately upon buying every disc based game that had any DRM. No DRM = no W7-10 issues at all. Quite a few games have also had it officially removed in later patches (Diablo 2, Neverwinter Nights DE, Operation Flashpoint Cold War Crisis, Prey (2006), etc) or side-stepped via source ports. It's been so smooth I genuinely forgot half these titles were originally DRM'd in the first place.
I have several big boxes of retail CD/DVD games for which I'm supposed to find such cracks, and I guess also try to move them to ISO format or something. Just so that I could run them also on newer Windows machines which don't have optical drives (I have one USB DVD drive though, but I am unsure if it in itself has some issues with old copy protections...).

For me one obstacle with this were that some cracks or noCD tracks appeared to be version specific, or then there was no clear indication whether the crack would work any version, and regional language version, of the game.

Also I am not even sure if the noCD crack sites that I used like 10-15 years ago are still around, and whether they can be trusted in not to try to insert malware with their cracks.

Luckily GOG has released a big portion of my physical PC game collection so those are now redundant and I could throw them to trashbin for all I care (as I have later bought the GOG versions of those games and they seem to run fine), but I still have lots of physical retail PC games that I'd like to be able to play. It seems to be easier and less time-consuming to try to find arrrrr-versions of those games online (abandonware sites or what have you), than trying to convert my own copies to ISO images and find working cracks for them, one by one.
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timppu: For me one obstacle with this were that some cracks or noCD tracks appeared to be version specific, or then there was no clear indication whether the crack would work any version, and regional language version, of the game.
Back in the day NoCD cracks had to be available for any game I bought unless the discs contained CDA-tracks or there were multiple discs per game full of FMV clips, but I no longer can recall how often it actually made any difference if I used a US or EU region crack. Version numbers were clearly marked though, unless the "crack" was just a mini-image that just had to be mounted to fool the CD-check, as then they would work with all later patches too as long as those patches change how the CD was detected.

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timppu: Also I am not even sure if the noCD crack sites that I used like 10-15 years ago are still around, and whether they can be trusted in not to try to insert malware with their cracks.
If you are not in a hurry, download the cracks, wait a few weeks and upload them on VirusTotal, although heuristics are likely to trigger a lot of false positives especially from AV-scanners you likely have never heard of, as bypassing DRM can easily be mistaken as actual malware messing with the execution order.

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timppu: ...but I still have lots of physical retail PC games that I'd like to be able to play. It seems to be easier and less time-consuming to try to find arrrrr-versions of those games online (abandonware sites or what have you), than trying to convert my own copies to ISO images and find working cracks for them, one by one.
Except that the upload limits on VirusTotal will make it rather difficult to figure out if this or that abandonware release is safe to run whereas you almost always can zip the latest crack from every crew together and still not exceed that upload limit.
One can also find pretty much anything for building a "modern" XP OS today. There's a driver update to allow 3TB+ drives to be used (KB4012598), and Paragon made one to allow GPT formatted drives (Paragon GPT loader for XP). When it comes to TRIM for SSD you need to use an external program to handle it manually, and disable prefetch, pagefile (or move it), and autodefrag. (I would recommend doing so regardless). Use Windows 7+ f.ex. to properly format the SSD.

Archive.org and wincert.net f.ex. has a lot for Windows XP including driverpacks for that neverending slipstreaming and unattended setups. (And yes, GCWorld is still around, but I think archive also has some too.)

And of course, nLite is still going strong..

I think both XP and Win 7 are not only fun to game on and use, they're also pretty stable and fast compared to the later versions. XP in particular is the last OS where you as an Admin can do pretty much anything. With Windows 7 and onward you're a basically a sheep and needs MS to decide for you, and by 11 you've completely given all control over to MS with the online-only profile.

I've had some trouble running certain early Windows games like C&C on 7 and 10 so XP is excellent for that, especially 16bit support, which is mainly why I bought some older HP workstations with i3 for. Personally, dual booting them both is well worth it and gives me the best of both worlds.

When it comes to XP and Windows 7 you're pretty much limited by hardware drivers to fully utilize the system. And for fun I built a 7 machine with Ryzen 5 5600G. The jury is still out. :D

Security wise it's not so terrible as some would like you to think. Main thing is to use a "relatively" up to date browser and a script blocker, and think very careful about which sites you enter. Though, if you dual-boot you might as well let Win 7 handle internet.
Post edited February 09, 2023 by sanscript
If you do dual-boot Windows XP and Windows 7, beware of the bug that deletes all Windows 7 System Restore points when you dual boot to Windows XP:

https://www.sevenforums.com/tutorials/8057-dual-boot-installation-windows-7-xp.html

By posting this link, at last I found a use at last for keeping that page bookmarked, even though I don't use Windows 7 myself no more (I only have an air-gapped Windows XP still besides my online Windows 10/11 machines).
System Restore is one the most trash functions MS has ever put out. It has "never" worked properly, neither at home nor at work. It's better to disable it entirely and instead use regular backup + something like Clonezilla and keep WinPE/Linux at hand. Much more reliable and more importantly, safer.

--
That reminds me: I usually boot up GParted/Parted Magic (old version) or similar to pre-partition the HDD before installing XP, and then 7.
It totally depends on your needs and circumstances
Can, have the stuff and eager to do it? Go for it, why not

And reading the hardware you have, your imagination, time & skills are the limit

Have fun
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AB2012: Posting this here for the benefit of those unaware but [url=https://www.pcgamingwiki.com/wiki/Glossary:DirectX/DirectDraw_troubleshooting]W7 DirectDraw Compatibility Tool[/url] and similar tools long eliminated the need to taskkill explorer.exe before play vs the "rainbow colour bug". All they do is enable a registry flag (per game) that enables W7's built-in fix. I have original Age of Empires 1-2, Diablo 2, etc, running as well on W7 as on XP "natively" (without the need for any wrappers).
I'd not seen that bug on my old Win 8.1 desktop.
On reading this thread, it reminded me I'd not installed original AoE and RoR on my new Windows 11 gaming desktop PC.
Both AoE and RoR get stretched from their 1024x768 max screenres, by my HP monitor, to fill it, 2560x1440.
I've yet to install the RoR UPatch HD, to see if that reduces the issue. That UPatch has a max res of 1920x1080, so my monitor might well stretch it to fill the screen.
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timppu: Also I am not even sure if the noCD crack sites that I used like 10-15 years ago are still around, and whether they can be trusted in not to try to insert malware with their cracks.
This is why you made backups on CD of such content.
I still have my original AoE and RoR noCD patches, but whether they'll work with the RoR UPatch HD, is another matter entirely.

edit: The RoR UPatch HD runs fine on my monitor in 2560x1440, so RoR is definitely playable on current systems.
Link to the RoR UPatch HD

edit 2: I've just finished playing through the first Hittites scenario from the AoE demo, in ROR with UPatch HD. I'd downloaded the demo campaigns over a decade ago now, extracted the individual scenarios, and converted the scenarios from AoE to RoR.
The scenario itself worked flawlessly. Only downsides were graphical. The videos are still hopelessly low res and their original ratio is not maintained, the scenario description maps are small, and the units in game are tiny now. Outside of that, the game works absolutely fine in Windows 11, on a current spec system.

edit 3: Age of Empires II Gold
Hello DRM.
CD 1, AoE II The Age Of Kings, can be patched to run without issue, full screen widescreen, with the Age of Empires 2 v2.0 patch from Age Of Kings Heaven.
CD2 AoE II The Conquerors, however is infected with the Safedisc DRM, and unpatched will not launch.
2 patches are needed to fix this.
1 - GameBanana - AoK Patch (1.0e)
2 - GamePressure - Age of Empires II: The Conquerors - User Patch v.1.5 (RC. Build 6268)
Installing patch 1 will get rid of the Safedisc DRM on TC, and patch 2 will make it playable full screen widescreen.
Post edited February 10, 2023 by JeniSkunk
deleted my duplicate post
Post edited February 10, 2023 by JeniSkunk
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timppu: Also I am not even sure if the noCD crack sites that I used like 10-15 years ago are still around, and whether they can be trusted in not to try to insert malware with their cracks.
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JeniSkunk: This is why you made backups on CD of such content.
I guess so, in case I had downloaded the content to begin with.

It is quite a task to try to find and download the latest official updates, and then noCD patches that are compatible with those updates, testing that they all really work together, and also making working ISO images... for e.g. 200 physical PC games, one by one.

I guess that is the reason why I never got around to do it, except for a couple of games maybe.

I think I once tried to make a working CloneCD or Alcohol image of my original Heavy Gear CD game, but never really succeeded in it. I googled for instructions and found some very complicated instructions how I was supposed to change some bits and bytes with a hex editor on some Heavy Gear files... oh and I thought those clone image utilities should have been so easy to use, especially for a game like Heavy Gear which I don't think had any really advanced copy protection like Starforce or SecuROM or whatever.

That experience kinda dismayed me, making the task seem even more unfeasible.
Post edited February 10, 2023 by timppu
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timppu: It is quite a task to try to find and download the latest official updates, and then noCD patches that are compatible with those updates, testing that they all really work together, and also making working ISO images... for e.g. 200 physical PC games, one by one.
That was always the complete not fun of needing to do that, and it hasn't changed at all.
Find the noCD that's supposed to work, install it, test the game, and be ready to try another.
And if it does work, then see if the game trainer plays nice with the noCD.
Fun times that haven't gone away.

I guess that is the reason why I never got around to do it, except for a couple of games maybe.

I think I once tried to make a working CloneCD or Alcohol image of my original Heavy Gear CD game, but never really succeeded in it. I googled for instructions and found some very complicated instructions how I was supposed to change some bits and bytes with a hex editor on some Heavy Gear files... oh and I thought those clone image utilities should have been so easy to use, especially for a game like Heavy Gear which I don't think had any really advanced copy protection like Starforce or SecuROM or whatever.

That experience kinda dismayed me, making the task seem even more unfeasible.
I bought a copy of Heavy Gear, when it was in the cheap clear-out bin at eb Games, back in 2002, I think.
Got it to run OK on my Win98 system, but I couldn't get into the game, just didn't click for me. Looking at my copy I see why it won't ever come to GOG, Activision game.

I made a few disk images using Alcohol. Games I'd bought, that it could reliably make a disk image of, so I wouldn't need to deal with excess wear on my CDs or drive. What I couldn't make a disk image of, then I'd go for the noCD. Main game I made the disk images of, was TES III Morrowind GOTY.

Making the CD backups of stuff downloaded was a necessity back then. You backed stuff up onto CD simply to be able to safely clear HDD space.
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JeniSkunk: Making the CD backups of stuff downloaded was a necessity back then. You backed stuff up onto CD simply to be able to safely clear HDD space.
I recall when CD writers were coming out, my dad got one for his business. The idea being you'd spend 50 cents to a dollar on a disc, but you could write session after session after session with the weekly backup of the data for the business, before it had to be finalized and could be put to the side in the event the worst happened.

Of course in 94-98, your data to back up for a small business was typically 100mb or less, and if you did incremental you could probably save more.

Actually i'd enjoy playing with Tape technology again if i could find something i was happy with that is very cheap and simple, just for fun.