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As far as I know the High Sierra update broke a lot of Wineskin wrappers. The most common fix I have seen is to:

• Open wineskin settings
• Choose "set screen options"
• Uncheck "autodetect GPU"
• Choose "Done" to close screen options
• Under "Tools" tab, "Utilities" section, open winetricks
• Search for "videomemorysize"
• Select a videomemorysize option from the list that corresponds to the VRAM of your video card
• Choose "Run"
• Choose "Done"

I believe some dummy-friendly steps from a few years ago will still work to port AGS games to mac. These steps are adapted from ryosan's post from this Gemini Rue thread:

1. First, create a new folder, put your game.exe file in there, along with any .cfg file and audio.vox you may have
2. Install Wineskin Winery app
3. Open Wineskin Winery, install latest engine and wrapper versions
4. Create "new blank wrapper". This will create a .app file
5. Find that .app file in finder, right-click (or control-click) on it, choose "show package contents"
6. Open Wineskin.app from the folder that appears
7. Choose Install Windows Software
8. Choose "copy a folder inside"
9. Select the folder from step 1 with your game files in it
10. Try running the app

This might work, or it might require further fiddling. Sometimes you may have to re-launch Wineskin.app and "Set Screen Options" to override resolution settings. But anyway, these steps have worked to port a few AGS games to mac, well enough for dummies anyway.

The AGS Awards nominations gave me a chance to play some games I hadn't seen before. If there's need for an upcoming community suggestion, I'd like to call out Cale Quest.