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Tries to run game... "Can't initialize Disciples 2".
Okay, I guess there is a configuration right? So I play with that a little: "Can't initialize Disciples 2"
Try changing Windows compatability modes: "Can't initialize Disciples 2"
Try reinstalling, because it's probably just corrupted or something right? "Can't initialize Disciples 2"

I'm tired of this. It's far from the only classic I have bought from the site that I have never got working. Here is the list of stuff I can remember off the top of my head (there are probably more):

Pharaoh Gold
Caesar III
DK2
Temple of Elemental Evil
Guilty Gear X2

HOMM3 and Planescape Torment had massive issues too, but after a lot of research and modding I managed to get them to play. I'm just tired of knowing that every game I buy, i'm taking a gamble. They SHOULD ALL WORK. My current specification, if it actually helps.:

Win 7 32bit
4gb ram
3.06 Ghz Dual Core
GTX 460 at 1366x768
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Where are you installing the games to? Many older games have issues if you install them to Program Files due to UAC. I've run Disciples 2, Caesar 3, ToEE, and HoMM3 on two different Win7 (x64) machines without any problems, so it's not an inherent issue with the games, but something about how they're interacting with your particular system (not trying to say the issue is on you- I'm well aware of how finicky some games can be with different configurations, just trying to figure out if there's something particular about your system and use case that's resulting in so many games having problems).

EDIT: Just recalled that I did have a few initial problems running Disciples 2 on one of my machines (it seemed to be rather sensitive to compatibility modes and wanting admin rights). I ended up needing to run it in Win 98/ME compatibility mode with "Disable Visual Themes" checked, then let it run with admin privileges when it asked (upon starting).
Post edited February 13, 2013 by DarrkPhoenix
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DarrkPhoenix: Where are you installing the games to? Many older games have issues if you install them to Program Files due to UAC. I've run Disciples 2, Caesar 3, ToEE, and HoMM3 on two different Win7 (x64) machines without any problems, so it's not an inherent issue with the games, but something about how they're interacting with your particular system (not trying to say the issue is on you- I'm well aware of how finicky some games can be with different configurations, just trying to figure out if there's something particular about your system and use case that's resulting in so many games having problems).

EDIT: Just recalled that I did have a few initial problems running Disciples 2 on one of my machines (it seemed to be rather sensitive to compatibility modes and wanting admin rights). I ended up needing to run it in Win 98/ME compatibility mode with "Disable Visual Themes" checked, then let it run with admin privileges when it asked (upon starting).
UAC is disabled on my machine, and has been since the day I installed Windows 7.

No change after applying your recommended compatability settings.
I looked around a bit and it looks like that even with UAC disabled there's still some restrictions on write access in Program Files. If you installed the game there then you should still try installing it somewhere else. If it's already installed somewhere else... I'm afraid that's all I've got in terms of thoughts on this. You might try looking at other topics in this forum, as there are a fair number dealing with Win7 issues with various other solutions posted in them.