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Oldest Windows version possible to run on Pentium D + 512mb RAM?

Depends on what you're wanting to do with it. If all you're going to do is run basic GDI applications, then even the really limited 640x480x4bpp is probably fine. If you want to run some of the early Windows games, VESA is going to be painful, at least in my experience.

In Windows 9x, I'd try to get any 2D acceleration that was available. Get an S3 Virge or something.
 
Clearly unacceptable! ;)

Honestly I think a more ”interesting”, if ultimately depressing challenge, might be trying to figure out what the *newest* OS you can get running, however badly, on a Pentium D. It is the first (consumer) x86-64 dual core cpu from Intel and one of the few 64 bit Netburst-based CPUs. It kind of defines the trailing edge, outside some similarly ancient AMD CPUs, of what remotely qualifies as “Modern” today.
i genuinely managed to run windows 7 32 bit on this piece of junk. the 64 bit crashed instantly.
 
That’s still about four years newer than the first Pentium D’s. Digging around it looks like Intel beat the Athlon 64 X2 to market by a couple weeks, so I guess it is officially the oldest consumer-grade dual-core X86-64. (Depending on which actual Pentium D revision it is.)

Anyway, from that digging it seems that the minimal chipset Intel recommended for these things was the 945-975 family, so if that comment about the 865 being the last chipset that worked well with DOS/Windows 9x is true then a Pentium D probably isn’t the optimal choice for some kind of retro-90’s gaming build.
The mb is a Foxconn N15235 with the AGP slots (I know there's at least one version with PCIe) it has a 964 chipset if I'm not mistaken.
 
Windows 98SE/ME will run on a Pentium D, depending on the chipset used. SiS and VIA chipsets tend to have weird issues. As for video, entirely depends on what video card was used. "Intel Extreme Graphics" didn't support 9x for very long, so "there be dragons" if trying to get an Intel IGP to work.

Nvidia supported 9x up to the Geforce 6 series. The Geforce 6200 is probably the best and easiest card to get running, but there were some weird 6600 and 6800 AGP cards.

ATI only went up to the Radeon 9000 series on 9x, with beta drivers for the x300-x800 series cards.

As for VESA support, be warned that VESA modes get very broken on cards released after 2000. YMMV on the UniVBE driver. But no matter the CPU speed, it will always be slow, and things that rely on OpenGL and DirectX won't work right, or run at all.
So should I run an actual GPU instead of integrated? The only "old" GPUs I actually have are a HD4850 Toxic and a 7600GT and these are after 2010 so I have doubts they'll work.
 
So should I run an actual GPU instead of integrated? The only "old" GPUs I actually have are a HD4850 Toxic and a 7600GT and these are after 2010 so I have doubts they'll work.
If you read my post, you'd know they won't. You'll need a video card I described if you want any driver support in win9x.
 
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