I noticed the first season of Sam & Max is marked as being compatible with Windows 10, whereas the second one isn't. I thought this might be simply because the second season hadn't been tested yet or something like that. I then noticed, however, that the Steam forums are full of people who can't run either season in Windows 10, and there's even a topic in the official Telltale forums discussing the problem.

This was pretty confusing at first, because I had checked the first episode of the first season (GOG edition) and it indeed seemed to be working perfectly. Then I remembered: the GOG edition uses a more recent build which, if I'm not mistaken, had upgraded the engine to that of the third season (hence why you can make Sam run in the GOG edition). However, I also remembered that the fifth episode of the first season (again, GOG edition) was at some point downgraded to the previous build because of some new bug. So I checked the fifth episode and, sure enough, that one didn't work. I didn't bother checking the second season, because I assume it will have the same problem, since it is not even marked as Win 10 compatible. I assume the people at GOG booted up the first episode of the first season, saw that it was working fine and then marked the game as Win 10 compatible, but they didn't take into account that the fifth episode is from a different build.

So beware: the fifth episode of the first season has the same (potential?) problem that has caused GOG not to mark the second season as Win 10 compatible.

So I am wondering: has anyone been able to run this episode or the second season out of the box in Windows 10? Is this a universal thing? It appears there is a workaround to make the games work (namely, forcing Windowed mode), but I haven't personally checked it.

On the Steam forum some people say the Season 2 GOG Version should work just fine.

I personally just wish that Telltale would update their game especially since i got the game on Steam and the workaround doesn't seem to work (at least for me) :/.
I even asked on Telltales Forum but they don't care for some reason.

I can't post links. I can't even post a text link. I own 290 games on this account, I've been registered since 2009, and I cannot post a link in a forum message. You guys will have to search and find on your own the right D3D9 installer and DX8 to DX9 converter. Sorry; the links were included in the original version of this post.

OS: Windows 10 v10.0.10586
Graphics Card: GeForce GTX 970
Graphics Driver: 361.75

I make no guarantee this will work, nor do I guarantee your computer won't implode. I investigated the errors that occurred during game startup and found this resolution. Based on other posts in this forum and Steam, I am wagering that these solutions will work for a great many of you.

Proceed at your own risk.

Install D3D9 from Microsoft. You're looking for "DirectX End-User Runtimes (June 2010)." Do not use the web installer; it will not install if it detects newer (DX11+) files.

As noted below, install the DX8 to DX9 converter enbdev.com into the game directory. (The file D3D8.DLL and ENBCONVERTOR.INI should end up in the same directory as the executable for the game, i.e. SAMMAX105.EXE.) While you can install the converter into the SYSTEM32 directory I advise against this in order to minimize any potential issues with other games.

If you're looking for solutions for the Steam version of the games, this should work as well.

All installations tested with an installer downloaded as of today, 2016/02/05. All tests were full screen at 1600x1200 (S1) or 1920x1080 resolution (S2 and S3). Obviously I didn't complete the full game, but I did complete a couple of puzzles in each. "Runs as installed" means that the game works after installation of D3D9.

101 - Culture Shock - Runs as installed.
102 - Situation: Comedy - Runs as installed.
103 - The Mole, The Mob, and the Meatball - Runs as installed.
104 - Abe Lincoln Must Die! - Runs as installed.
105 - Reality 2.0 - Install DX8 to DX9 converter; runs afterwards.
106 - Bright Side of the Moon - Runs as installed.

201 - Ice Station Santa - Install DX8 to DX9 converter; runs afterwards.
202 - Moai Better Blues - Install DX8 to DX9 converter; runs afterwards.
203 - Night of the Raving Dead - Install DX8 to DX9 converter; runs afterwards.
204 - Chariots of the Dogs - Install DX8 to DX9 converter; runs afterwards.
205 - What's New, Beelzebub - Install DX8 to DX9 converter; runs afterwards.

301 - The Penal Zone - Runs as installed.
302 - The Tomb of Sammun-Mak - Runs as installed.
303 - They Stole Max's Brain - Runs as installed.
304 - Beyond the Alley of the Dolls - Runs as installed.
305 - The City That Dares Not Sleep - Runs as installed.

Further help: if the game still isn't running for you find the game executable (SAMMAX###.EXE where ### is the episode number), right click it and choose Properties, then go to the Compatibility tab. Ensure "Run this program as an administrator" and "Disable display scaling on high DPI settings" is selected and try again. If that doesn't work, select Windows Vista SP2 under "Run this program in compatibility mode for..." and try again. If both of those fail, try running the compatibility troubleshooter - but that usually only results in the settings above.

Finally, the error message "such and such has stopped responding" or the like doesn't help much but generally more information is logged to the event log. Search for "Event Viewer", expand Windows Logs, then select the Application Log. Look for the most recent error (it will have an exclamation point in a red circle) and see what information is presented there.

Good luck.
Talonius