Run wine totally headless

You can configure your wine to run headless by installing X virtual framebuffer. For instance:

sudo apt-get install Xvfb
Xvfb :0 -screen 0 1024x768x16 &

Install wine:

# On 64-bit also run: sudo dpkg --add-architecture i386
sudo add-apt-repository -y ppa:ubuntu-wine
sudo apt-get update
sudo apt-get install wine

^{Note: For detailed installation example, check provision.sh script.}

Install fonts if required:

winetricks allfonts

Then run your apps as:

DISPLAY=:0.0 wine my_app.exe

or you can export it (so no need for the above prefix when running):

export DISPLAY=:0.0 # Select screen 0.

Where DISPLAY is your request to local display/input service (or: export DISPLAY=[user's machine]:0).

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Alternatively set-up X11 Forwarding. Then you don't need to use DISPLAY.

Basically set X11Forwarding yes in /etc/ssh/sshd_config on the headless server and ForwardX11 yes in /etc/sshd/ssh_config on the machine you're connecting from.

Then you can run GUI applications on your headless server and at the same time wine will be able to connect to your local X11 server, so you could run your console-based DOS executables.

I don't know any way to run wine totally headless but I can point you to xvfb. It can create a virtual display to which X server can redirect its output. No need to have a physical display connected. We use it to run selenium tests in browsers on a headless Jenkins cluster.

Does that meet the requirements or are you bent on running wine absolutely headless?