I have the original OUTLAWS and CD and they all work fine except for one of the "Historical Missions." I believe it is the Civil War map which is divided into two halves. When I get the second half of the mission it crashes and I have never been able to resolve this. My experience is that GOG.COM doesn't always solve these bugs, so I want to know if anyone else is having this problem and if it has been resolved, or how to resolve it. Thanks :)

I am on the second mission, have not finished it, but have not crashed either.

I never had this problem with my retail copy - but I am not saying that it does not exist, as I heard about it previously, the only thing I can say is, try to change rendering mode both for graphics and audio via olcfg.exe and if it does not help, change the computer - I know, this is easier said than done... :-)

Civil War map is huge (that is why it has been split into two parts) and it is generally speaking, pushing the engine to its limits - therefore, it is more prone to crash than others.
Same could be said about Wharf Town, which, on the other hand, had the tendency to push the graphics to the limits in 3D mode (I do not think that this is an issue today - but what do I know...).

Beat it twice now, no crashes. Don't remember the general at the end being that short, though.