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From previous non-GOG games of Sam & Max I've played, whenever I have saved the game a screenshot of my current location has appeared in the slide next to the save\load buttons and time and date.

It seems that now, or perhaps it is only the GOG version, these slides remain blank and do not display the picture. This issue was present all through episode one, and I'm playing episode two now and seeing the same issue (see screenshot). Quitting and re-opening the game didn't help anything.

Is this happening for anyone else, and if so has a fix been found? It's not a game-breaking problem because I can still read the dates, but it's a fair bit of a disappointment that I can't see what I've saved for or where I'm saved at.
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I've never seen that before, but it doesn't surprise me. Season One of the Sam & Max games (at least the GOG versions) seem to have a number of graphical glitches; nothing too serious (except for a game-breaking issue with Episode 5, hopefully fixed soon), but this is definitely annoying.

You should send GOG a support request - use this link:
http://www.gog.com/en/support/contact/technical_issues_with_games/sam_max_save_the_world
Thanks for your suggestion.

I've just submitted it to the link you posted, so I'll wait and see if those brainy GOG people will have any ideas.
Running the game as an Administrator (on Windows 7, at least) and then saving will associate the save slot with a screenshot. Saving into a save slot when the game is not run as an administrator (on Windows 7, at least) will either not put in a screenshot or will remove the existing screenshot, if there is one.

I should probably have tried running the game as an administrator before but I'd considered it and discarded it as unlikely to make a difference - I fail to see how the game needs administrator privileges to be able to take a copy of its own render buffer.

I imagine the earlier games I have played where there were no such issues on screenshots were played on Windows XP, which was rather more lax about administrator security.