Running Quest on a Mac using Wine or CrossOver

I installed CrossOver 19.0.1 tonight and thought I’d try to install Quest in it. I have had a very bad experience trying to run Quest competition games on the Mac via the Quest web server - sluggish, and usually seizing up, and forgetting state constantly. So I thought this might be a better solution for me.

Sadly it hasn’t worked well. I have tried installing Quest for Windows 5.8, 5.6, 5.0 and 4.0.5. 5.6 got the furthest. I had to install .NET Framework 4.0 to get it installed. And then I thought I had it sorted. But the program window is flickering constantly, and crashes whenever I try to load in a game.

Has any other Mac user managed to get Quest for Windows running under Wine or CrossOver? If so which version(s)? Also any other pertinent tips?

Many thanks!


Still stuck, but a bit more info. Under a Windows 7 CrossOver bottle trying 5.6 after a .NET Framework 4.0 installation I can fiddle with the graphics setup to reduce the flickering. But when I try to open a Quest game file I get this error, even if I’ve turned off play sounds and speak in the Quest options.

I suspect it’s an admin/permissions issue, but I don’t know how to fix it.


A bit of googling finds someone else running into the same problem, with a Wine installation on Linux.

CrossOver is a slightly user friendlier version of Wine.

I had good luck just running Windows via Parallels on my MacBook Pro. Under Parallels / Windows I could run just about any Windows app.

Might be a good alternative.


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I’m not a macOS or Crossover user, but I have spent a fair amount of time before various comps start trying to get the Quest player to work under Linux with Wine, and I have basically given up on making it usable that way.

My best guess, based on the time I’ve spent poking, is just that .net 4.0 and some other versions just don’t play nice under Wine, and there aren’t good Wine replacements for them. This seems to be a problem with other .net applications on Wine for me, too (other people seem to complain about it). I have given up on other .net-based applications that I just can’t get to run under Wine, too.

I don’t know whether .net has better support under Crossover, but it might just be that you’re hitting a problem with an underlying library not working well enough to make the application that depends on it reliable. (Or perhaps not. Perhaps there’s some other solution that I haven’t tried yet.)

Anyway, the only way I’ve ever been able to get the Quest app working is to run it under Windows in a VirtualBox. For several years this has meant that I just don’t get around to Quest games during the Comp.

I hope you have better luck.

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Many thanks @fos1 and @patrick_mooney for the helpful replies.

I’d hoped to get Quest running on my Mac, but not badly enough to want to shell out the higher cost for Parallels or a working version of Windows for VirtualBox. Ah well!


Honestly. $139 for a home copy of Windows 10 seems like a high price to pay to get Quest games running on my machine. Windows 7 and 8 are not much cheaper.

I do not mean to be snarky about Quest or other Windows-only development systems, but it’s a development choice that authors make. If it happens to exclude me, intentionally or otherwise, well, then, intentionally or otherwise, I am not the target audience for the game. There are always more games in the IFComp then I can get to. :slight_smile: