Cannot launch Steam game with Wine

Question

I have 2 computers. One is Mavericks (10.9.5) and this one is Yosemite. On Mavericks, this works flawlessly. With wine, Steam launches fine. However, there is a peculiar window showing up, and whenever I try launching a game/app, it pops the usual window with "Preparing to launch...", then it disappears and nothing happens.

The image on top shows the unusual window showing up next to the main window.

This is my setup in Wineskin of Steam (needs -no-dwrite because else, it shows blank buttons).

Here and here are the 2 Last Run log files.

UPDATE:

Reinstalling didn't help, and I figured out what the little window is. On Mavericks, it was on the navbar on top, and on yosemite, it is in this window. Clicking it shows the same options as the Steam icon on the navbar on Mavericks. Also, I may have found something related in the logs:

err:winediag:SECUR32_initNTLMSP ntlm_auth was not found or is outdated. 
Makesure that ntlm_auth >= 3.0.25 is in your path. Usually, you can find it in the winbind package of your distribution.

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I am using OS X Yosemite (10.10.3)

Answer 1

The difference may be related to whether you're using the Mac driver. Go to Set Screen Options, and check Use Mac Driver instead of X11. It's the top checkbox under "Other Options".

Otherwise, it's not clear how your installations are different. Because you're using Wineskin, however, you have a great alternative: Just copy the Wineskin app from your working computer to this one. That will carry along all of the settings and tweaks you have in your working copy. It's all self-contained!

Answer 2

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it's something about 32bit vs. 64bit.