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I launch Sims Medieval  and I get this from the debug screen.

[10/19/13 21:53:56] - Running wine-1.5.31  (Working directory : /home/XXXXXX/.PlayOnLinux/wineprefix/thesimsmedieval/drive_c)
wine: cannot find ''

Aangepast door Seafire

That is the whole debug? Are you sure there isn't anything else?

Try launching Sims by clicking the game icon, then clicking Debug instead of Run.

As far as I can tell that is the whole debug.

Went to .PlayOnLinux/wineprefix/thesimsmedieval/drive_c/

It exists, so I am not entirely sure what the problem is.

P.S. The game doesn't even launch. You click run and an error is immediately generated.

Aangepast door Seafire

Try launching the game by selecting the Sims icon and clicking "Debug" on the right side.
Don't click Run

Then the debug will pop-up and run all the errors
Then you can copy paste it here.