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I have Windows XP in a VM within OS X Lion, but I'd like to run Diablo in its own window for when I put Parallels in Coherence mode. I can't resize the window once it resets the resolution to 640x480 and goes full-screen. Is it possible to run it in a window within Windows without another VM? Adding the usual windowed mode flags (-w, -win, -window, -windowed) to the shortcut's target field doesn't work (though -w works with D2). (Is there another established method for windowing old, stubborn programs like D1?)

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You can try running it in a virtual machine like Virtual Box. –  Krazer May 3 '12 at 3:48
    
Diablo doesn't have any native support for windowed mode. The only way I know is a virtual machine. –  Dracs May 3 '12 at 4:25
    
A Virtual machine works perfectly, if your pc isn't like 10 years old. Maybe someone should turn this into an answer. –  Timothy Roy May 3 '12 at 12:35
    
Have you tried Alt+Enter? –  Nick T May 4 '12 at 4:36
    
@NickT Yep—no dice –  Sean May 4 '12 at 4:39
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2 Answers

A virtual machine running on Virtual Box will probably do the trick. One of the main downsides of trying to run games on VM's is the slowdown from virtualizing modern graphics, which is totally not a problem here! Further, you should be able to avoid any windows compatibility problems by just installing Windows 98 in the VM.

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1 that would have been my suggestion as well... –  Zommuter May 3 '12 at 20:40
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This post offers some insightful information on installing D1 on Virtual Box.

General > Advanced > Untick "Show Toolbar in Fullscreen;"

Audio > Host Driver > Alsa Network > Bridged Adapter;

Select Windows as the installation media, then install;

Install guest additions, then enable their offered graphics capabilities;

Every time one restarts the virtual machine, consideration should be given to:

Cut down host resolution (integer-value native division; aspect-ratio maintenance) through its system settings (useful for cases in which the resolution is of 640*480);

Switch to fullscreen mode through holding down the host key*, then pressing the f one;

Disable mouse integration through holding down the host key*, then pressing the i one;

*By default, this is the right Control key on your keyboard; on a Mac host, the default host key is the left Command key

For more information on Virtual Box, consult the manual here.

WineBottler works as well. The process is about the same as installing D2.

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