Getting Chessmaster 9000 to Work in Windows 10

No, I don't think so. That's a price I'm willing to pay, but others may not be so willing. There aren't very many chess programs that run in straight Linux. The programs I have installed on Linux are Arena, ChessX, PyChess, Scid, Scid vs. PC, and Xboard. Also, the engines have to be compatible with Linux, so your engine choices are limited, too.

However, there is Wine (sort of an emulator, although the name Wine stands for Wine Is Not an Emulator) that might be able to run some Windows chess programs. I haven't installed Wine, so I don't know exactly which ones might work in it. But from what I've heard, even if a program runs in Wine, there are varying levels of compatibility. Some programs run almost perfectly, others not so well. (The reason I haven't used Wine is that there's a slightly higher level of security risk when you run Windows executables in Linux.)

And, your question is why I kept my Windows 7 hard drive. If push comes to shove, I can boot up into that and play stuff that I had on Win7. The downside is that when I'm in my Win7 HD, I'm not on the internet.

Another option is to use VMWare on Windows 10 to run a Windows 7 virtual machine. You can run your retro software on Windows 7 without needing to buy a retro computer.

You've piqued my interest.  I'm going to find my old CM9000 and see if I can boot it up.

I'm getting the same thing as Nimzowitts.  Looking at the Events generated may give a clue:

and the second error:

After further research, came up with this helpful page.

It apparently has to do with the copy protection being used, along with MS dropping support for it in later versions.  I will not be taking the workaround steps recommended (go to page 23), since it would be a security concern for me.

My question is what makes EscherehcsE's install work while mine does not.  Perhaps there was something that loaded that old driver service?
 

That's a good question. Is it possible that my CDs don't have the copy protection and your CDs do have the copy protection? I have verified that I can burn a copy of the CDs, and those copies work just as well as the original discs. My discs are copyrighted 2002. The article I read mentions that SafeDisc and SecuROM appeared on discs between about 2003 and 2008.

https://www.howtogeek.com/230773/HOW-TO-PLAY-PC-GAMES-THAT-REQUIRE-SAFEDISC-OR-SECUROM-DRM-ON-WINDOWS-10-8.1-8-7-AND-VISTA/

I don't know much about copy protection. If a disc is copy-protected with SafeDisc or SecuROM, would you be able to burn a copy that would also work? (In Windows, I typically just use Imgburn.)

All very interesting. On my machine it does indeed act like copy right protection issues kinda like the old 3 installs only of 90's programs like Genius, M chess etc.   I am looking all over my recently aquired CDs but the print is SO small my old eyes can not see it even with 3 pairs of reader glasses on!

Also interesting that the linked article mentions that perhaps games that are downloaded may not have the copyright protection. Now WHERE on Earth could I download/purchase a CM 9000 like that???

Once again I found a download link that claims the Cm9000 program will work on windows 10 and can be downloaded. Apparently they did SOME KIND of fiddling with the program as they have got it work but I am loathe to trust unknown sites. I ran their site https://www.old-games.com/download/6808/chessmaster-9000  through Norton Site checker which said it was fine however IMHO that means nothing.

Further there  is a slight  fee (Via Pay Pal etc.) so I wonder if the site MAY be legit.

I just tried a site checker called sucuri that gave it the ok as well.

I have a copy of that file. It's actually a GOG digital download. I guess there's no way to know for sure whether it's been doctored, but it seemed to work OK on my Win10 test rig. I only did a spot check of the various features, but everything I tried seemed to work.

I tried to upload the file to VirusTotal, but it's larger than the maximum file size that VirusTotal will accept.

This site https://www.urlvoid.com/  seems to give it an OK as well. The OLD GAMES site is based here in America, or at least that is what is purported. Perhaps it IS legit?

I will investigate further tomorrow. I certainly will pay the slight fee IF it is kosher.

Well, there are a few programs that they offer that don't seem right (Fritz 9, etc.). There are definitely some newer games that you wouldn't think they got permission for. But mostly just abandonware, which I doubt many companies care about. My guess is they go as far as they think they can get away with without the lawyers noticing.

Fritz 9 is sold at Amazon for $17.00 but that comes with a year membership at Playchess according to the advert. Chessbase would never offer a year's membership for that low of a price. Hmmmmmmmmmmmm

Here's a CD set on Amazon that's the same packaging as mine - EXCEPT if you look closely, Disc 1 appears to have a copyright date of 2007; mine is 2002.

https://www.amazon.com/Electronic-Arts-Chessmaster-9000/dp/B0032TIXPU

The packaging is identical in every way (even with a 2002 copyright, I think - hard to read), but the copyright date on Disc 1 is different.

If this is the cause of all our problems, I guess I'm holding golden discs, lol.

Good grief!! I think that such IS the issue!  MUST be some way to bypass or find OLD discs. WHERE did you find the date on your original discs?