Okay, I clicked on the little wineglass after starting wine, and found the configuration menu. After inserting the disc, I got it to recognize the DVD drive as drive D:, and even got so far as using the menu to access the installer and install the game. Now, the bad news. When I try to run the game, it prompts me to insert the disc again, even though it's still in the drive. I navigated to the DOS prompt in Wine and typed PATH and noticed D: was not in the PATH statement. Could this be causing the problem? I looked here https://www.winehq.org/docs/wineusr-guide/env … nment-variables on how to edit Wine's PATH and it told me to use wine's regedit to change environment variables. I did, and in the Current User section, PATH wasn't there, only TEMP and TMP. What now?

That's about as far as I can help without the game.

lee292 wrote:

I navigated to the DOS prompt in Wine and typed PATH and noticed D: was not in the PATH statement. Could this be causing the problem?

Probably not. I can't really think of a scenario where that would be a problem.

Sometimes a program will try to read a disc's volume label. On your Windows machine, does the disc have a name in Windows Explorer? In a command prompt in Wine, if you type "dir d:", does the first line say "Volume in drive D is <something>" ?

Found the paths in regedit and changed them, and it didn't work. The disc is shown as D:\Scrabble when you type DIR. This one's a pig. As said before there's a version of the game, albeit stripped down, that will run on Mountain Lion, and there's the old one that can be bought that runs on Snow Leopard, which I have on a disc partition. If I count my time, I've spent more trying to get this beast to work that it would take to buy another game.

lee292 wrote:

The disc is shown as D:\Scrabble when you type DIR.

A disc's volume label would never be shown in that format (unless Wine has somehow become extremely weird since I last used it), so I'm not sure if you're referring to what I'm thinking of. Like I said, the very first line (before any files or anything else) should state either "Volume in drive D is <something>" or "Volume in drive D has no label".

It may be helpful at this point to post a screenshot to ensure we are on the same proverbial page.