How is the printer connected to the server? Serial, Parallel, USB or network
If it is a physical port, you need a port capture program to capture the print stream from the server to a file. If the printer is on a network, you can run a lpd daemon to do the same thing. Then you can pump the captured file through a virtual printer (either Postscript, PCL or maybe HPGL) to get a fax-able output. It would be easier to do this sort of thing with a Linux box, but it should be possible to do it with Windows as well, just a bit trickier.
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