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Apparently around a month ago, HoMM 2's GoG release has been set back to its 1.0 version? I don't know what has happened here, but "updating" to this version sets the game back to how it worked when first released on GoG...You can no longer change the music, for example.

And I am not able to play single-player, the game will tell me I am missing the CD file? If I use the Win95 shortcut, the game works as normal and I have found no trouble launching this way. If I revert to one of the other available version numbers, the problem of the game not recognizing the existing of the CD file persists.

I've tried file verification and repair, other forum posts have not seemingly had this trouble, and I haven't been able to solve this problem on my own. Any help would be appreciated!
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Sielith: Apparently around a month ago, HoMM 2's GoG release has been set back to its 1.0 version? I don't know what has happened here, but "updating" to this version sets the game back to how it worked when first released on GoG...You can no longer change the music, for example.

And I am not able to play single-player, the game will tell me I am missing the CD file? If I use the Win95 shortcut, the game works as normal and I have found no trouble launching this way. If I revert to one of the other available version numbers, the problem of the game not recognizing the existing of the CD file persists.

I've tried file verification and repair, other forum posts have not seemingly had this trouble, and I haven't been able to solve this problem on my own. Any help would be appreciated!
It would be of interest to know if you can get HOMM2 v 1.0 to run at all at this point; mine will no longer run at all, as of the last couple of days, and I had it on 2 PCs.

Um... if, at some time in the past, you had downloaded the offline installation software for HOMM2 prior to their reverting it to v 1.0, their automatic updater will not update offline installations. So, if by chance you have a later offline installation version, such as I found that I did, you can safely install that and not worry about GOG automatically "updating" it to v 1.0. And... the later version still runs; whatever broke v 1.0 in the latest GOG updates doesn't impact the more recent versions of HOMM2.

What clued me into this was that my laptop had an offline installation of HOMM2 v 2.0.etc., and it's working fine; copying the installation software I found stored on that PC, I was able to get back up and running on my other PCs.

GOG makes it very clear on their website that offline installations will not automatically update; they point this out as something to be aware of since you won't get any improvements released, but in this case... what they released weren't improvements, now were they?

And whatever broke HOMM2 v 1.0 for me isn't related to it being run via DosBox; my other GOG DOS games running via DosBox are working just fine.
I don't think I have an offline installation. I tried fully reinstalling it again, but no change to the dos version of the game...The Windows version pack-in works perfectly still though. No idea what's happened with it, but since this version still works and hopefully GOG can catch what's going on and be able to fix it?

Thanks for the advice though, I'll check to see if my laptop has an older offline installation and see if doing what you've done will work for me...And if not, at least the Win95 port runs? *shrug*