After messing around a while getting this to run on Windows 8 (technically Windows 8.1, 64 Bit), I thought I would post my 2 cents on the best way to get it to run.
1. Download and install AAStarterPackFull60.exe (or Install from the original CD, then download and install AAStarterPack60.exe).
2. Copy the Data folder from the CD to the Programs directory if music/videos are desired (typically C:\Program Files (x86)\Hasbro Interactive\Axis and Allies).
3. Run AAHelper, uncheck “Enable DirectDraw Emulation”, and set “Limit Process Affinity” to “On when Movies Enabled”.
4. Download an updated drawfix file. I can’t post links, but you can find it on the page linked to by aqrit above (see his Feb 26 2013 post on that page). Extract drawfix.dll from the zip to the Programs directory, replacing the original.
5. Run the game. While in the game, hold Alt and hit enter twice. This will change out of and back to full screen mode. You will need to do this step each time you launch the game.
A couple notes:
- I did not have to set compatibility mode to a previous windows version, or have the program run as administrator.
- If you skip the last step above there will be some bugs in the program, most notably some slow animation. For example, the battle screen with the dice will take 5 seconds or more to load before every battle. For some reason changing out of full screen and back makes it run at a realistic speed.