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I'm no Wineskin wizard, but I managed to get Ground Control and the Dark Conspiracy expansion running on my iMac, so I thought I'd describe what I did here in hopes that this info will be of use to others ... and perhaps of getting some feedback from folks better versed in the use of Wineskin.

Engine and wrapper

I used the latest engine (WS9Wine1.9.24) and wrapper version (Wineskin-2.6.2) and they seem to work okay.

The goal is to get the game working reliably with hardware rendering, as software is limited to 640x480.

Expansion Setup

When you the install the game in the wrapper, the GOG setup program will automatically install the expansion pack as well ... but the wrapper will automatically be set to run the base game. To use the expansion pack, you need to add a command-line parameter after the game program's filename.

The easy way to accomplish this, assuming you want to have both the base game and the expansion pack available at all times, is to create a duplicate of your application file. Let's say you sensibly called your wrapper "Ground Control.app". Click once on that, press Command-D to duplicate the application, and rename the new file something like "Dark Conspiracy.app". Now run the "Wineskin.app" inside the duplicate app, open the Advanced settings, and add the following in the "EXE Flags" field:

-mod DARKCONS

Once you've done this, you can launch the duplicate app when you want to play the expansion pack.

Results

I haven't spent much time playing the game yet, but I've spotted a few issues. Occasionally the game will flicker if I click through the intro videos too quickly; when that happens, just quitting and relaunching the app will fix the problem.

I've also noticed that many objects (such as buildings) may pop in and out, or are not rendered at all, when using the Mac drivers. Most frustratingly, the game doesn't render the beacons in the "Boot Camp" tutorial, which makes it impossible to continue the tutorial past the very beginning.

LATER: Texture dropout seems marginally better with an earlier engine (WS9Wine1.5.27) but it's still not perfect. Buildings don't pop out as frequently, but the beacons are still absent.

At the moment, it looks like software rendering is the best option ... in that case, the "Use Mac Driver" option can be disabled.

LATER: Hmm. It works fine with software rendering ... for a while. Got a crash partway into the second mission.

If you can add any advice on running Ground Control Anthology on the Mac, or come up with further issues resulting from this setup, please feel free to post below!
Post edited December 11, 2016 by Midville
Thanks a lot for this guide. I am currently on the fence about purchasing GC Anthology, and I only have a mac.

Just a quick question: would you say the game is playable on the mac, did you encounter any critical bugs, and generally how stable did you find it running under Wineskin?
Sorry it took so long to respond ... health problems in the family have kept me busy the past year.

It's been a while since I tried fiddling with this game, as I ran into some issues as a result of a macOS upgrade. I eventually gave up on trying to get it work, and played Ground Control 2 instead.
Post edited October 14, 2018 by Midville