You might check into Chessmaster Challenge. It has all the tutorials and is basically a stripped down version of the old Chessmaster program. I believe it is considered abandonware now.
Chessmaster 10th Edition not running on Windows 10 laptop
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What worked for me before were the UK versions of the patches, not the US versions. See the files from this site:
https://patches.ubi.com/chessmaster_10th_edition/
I'm not sure if the UK patches still work on the latest Windows 10 OS versions, though. I haven't used any Chessmaster product (apart from the engines) in three years.
Nov 28, 2023
0
#6
I tried a different tact. Downloaded iso files from abandonware, mounted them on virtual drives. Installed the uk patches. Ran as admin with compatibility. Turned off av. Disconnected from internet. Still no go.
bdcburton wrote:
I'm hoping someone might have a helpful suggestion. I've managed to install Chessmaster 10th edition on an old laptop running Windows 10. It took several tries - but running as an administration with XP SP3 compatibility setting seems to have enabled the installl. The shortcut is on the desktop - but when I click it, the program itself doesn't start. Rather, I'm asked if I want to allow Chessmaster.exe or Autorun.exe to change the hard drive, etc. At least no error messages! But even after installing the three patches from ubisoft, I'm still dead in the water. Can anyone help? Chessmaster was the first PC chess program I used, probably 15 years ago. I'd like to work through the tutorials and the Waitzkin annotated games, etc.
I know you probably can't run Windows 11 on an old laptop but I could run Chessmaster 11 with no problems in Windows 11. I now run Linux Mint on a new PC and can run Chessmaster 11 but the thinking lines don't work. Chessmaster Challenge runs well using WINE with the tutorials and everything else. Depending on how big your hard drive is installing Mint or Ubuntu alongside Windows would give you an option for running some programs that won't work under Windows 10. I can even run Chess Genius Classic under WINE which is impossible to run on a 64 bit system. I personally don't even mess with Windows anymore.
Nov 28, 2023
0
#8
Released in 2004? It must be intended to run on an early version of Windows XP.
Have you tried running it in an XP Emulator shell? Or in DOSBOX?
Nov 28, 2023
0
#9
I see if I can figure out how to do some of those suggestions! Maybe even back the compatibility up to earlier versions of XP. I quite out of my depth already ... but I'm still swimming.
If you have sufficient RAM and cpu cores, you can try setting up a Windows 7 or even an XP virtual machine using VirtualBox or VMware.
Hello there! This is my first post ever on this site, even though I have been a member for 13 years. I consider myself a novice, but I'm trying to improve my chess skills by using Chessmaster on Windows 11. I'm even using Stockfish 15 to enhance my experience. I have official CDs that I bought many years ago, which I first converted into ISO format using a freeware program. After installing the 3 updates, it works extremely well, with only a few minor crashes that I'm still trying to figure out, especially after it gives natural language advice. However, I'm confident that I will work it out eventually. I have a database of over 1 million games (I know it's not that much!) and I'm currently working on upgrading personalities and open books. So my advice is keep looking for answers 
or always send me a message if you want a quick fix. I have CM11 Grandmaster version as well but Like you Chessmaster 10 was probably the first program I used. I think it fell along the wayside simply because I upgraded windows and it wouldn't play anymore. Recently I started to try to improve my chess and my first thought was CM10 and It helps me enormously. I just wish there is a fan base just for this because it has so much potential. I am sorry chess.com you help as well but diamond membership is so expensive in comparison and you know it. I still love you though. please dont delete me
Ok there was a crack to use as well, so this would install; which I was forced to use even though i paid my dues. I think it came from some major chinese hacker who calls it dragonball2 but what do I know. I don't speak chinese at the best of times, he/she helped me run a program I paid for so what the hell! I have probably got the same software someplace safe. Anyway it helps me run a Chess Program I love (2 x Chess Programs) and I Will not link it here but may under duress suffer waterboarding to disclose the whereabouts on the internet .. someplace closeby. I think . ARRGGGhhhh the Paininn .... contact me quick Before I am deleted for being a Muppet
I'm hoping someone might have a helpful suggestion. I've managed to install Chessmaster 10th edition on an old laptop running Windows 10. It took several tries - but running as an administration with XP SP3 compatibility setting seems to have enabled the installl. The shortcut is on the desktop - but when I click it, the program itself doesn't start. Rather, I'm asked if I want to allow Chessmaster.exe or Autorun.exe to change the hard drive, etc. At least no error messages! But even after installing the three patches from ubisoft, I'm still dead in the water. Can anyone help? Chessmaster was the first PC chess program I used, probably 15 years ago. I'd like to work through the tutorials and the Waitzkin annotated games, etc.