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I feel like I'm going crazy, I played Underworld 1+2 about a year ago on Mac and I swear I was able to go from fullscreen to windowed mode and back at will, but I can't figure out how to do it. Before you ask, I tried Command + F but it does nothing. Any help would be appreciated.
This question / problem has been solved by 01kipperimage
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robynred: I feel like I'm going crazy, I played Underworld 1+2 about a year ago on Mac and I swear I was able to go from fullscreen to windowed mode and back at will, but I can't figure out how to do it. Before you ask, I tried Command + F but it does nothing. Any help would be appreciated.
GOG's DOS games for Mac used to be run on Boxer. However, boxer has 32-bit elements and is no longer compatible with macOS 10.15 Catalina and will not run on that OS.

Therefore, GOG is updating their DOS games to run on DOSBox instead, which is Catalina-compatible.

The difference you note is the difference between Boxer and DOSBox.

If you are NOT using Catalina, you can download Boxer yourself separately (http://boxerapp.com/) and run the games with that instead. You will need to locate the game files within each game's GOG app to add them to Boxer. If you have any trouble with this, let me know and I can help you (it can be hard to find the first time you try, but once you know where to look you should be able to find them for all games).
Well this is embarassing - see, I was using Mojave when I was trying to play Underworld 1+2 again, and besides the windowed mode issue, I was also having a weird problem where whenever I quit either game, whether with keyboard commands or within the game, for some reason it would take me to my Mac logout screen, forcing me to log back in and restart all my programs. After trying to fix that without any luck, I finally upgraded my Mac to Catalina to see if that would help - and it did! I have no idea why it worked, but both games now quit normally. But now I see I've kinda screwed myself over in regards to the windowed mode situation. I don't think downgrading is an option for me so I guess I'll just have to deal. Thanks anyway, I appreciate the explanation.
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robynred: Well this is embarassing - see, I was using Mojave when I was trying to play Underworld 1+2 again, and besides the windowed mode issue, I was also having a weird problem where whenever I quit either game, whether with keyboard commands or within the game, for some reason it would take me to my Mac logout screen, forcing me to log back in and restart all my programs. After trying to fix that without any luck, I finally upgraded my Mac to Catalina to see if that would help - and it did! I have no idea why it worked, but both games now quit normally. But now I see I've kinda screwed myself over in regards to the windowed mode situation. I don't think downgrading is an option for me so I guess I'll just have to deal. Thanks anyway, I appreciate the explanation.
I did a bit more investigation, and you can switch to a smaller window with DOSBox, you need to press "option-return". However, this window is very small and is not re-sizeable like it used to be with Boxer. Also, you can't easily switch your mouse cursor to move it outside the small window (you have to use "command-option-esc" to get your regular mouse cursor back). *I'm not using Catalina, but I don't imagine it would be different in this particular instance.

I've never had that problem with DOSBox logging me out so I'm not sure what was going on there, but I'm not using Mojave either.
Post edited December 13, 2019 by 01kipper
That works! That will do just fine, thanks for the help.