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I'm trying to find a way to run an old Dos based application that uses a printer connected to the parallel port, I don't think Dosbox supports lpt.

I am interested both in using that printer and in trying to emulate the printer somehow and connect a USB based printer.

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You can use one of the patched/forked versions of DOSBox that support printing. There are a few.

One I've recently started using is Taewoong's enhanced "ykhwong" version (as of writing, it was last updated Oct. 12. 2011):

Included Patches:

Direct3D with pixelshaders, OpenglHQ, Innovation, Glide, zip/7z mount, Beep, NE2000 Ethernet, Graphis user interface (menu), Save/Load states, Vertical sync, CPU flags optimization, Various DOS commands (PROMPT VOL, LABEL, MOUSE, etc) and CONFIG.SYS commands (DEVICE, BUFFERS, FILES, etc), Continuous turbo key, Core-switch key, Show details (from menu bar), Nice DOSBox icon, Font patch (cp437), MAKEIMG command, INTRO, Ctrl-break patch, DBCS support patch, Automatic mount, Printer output, MT-32 emulation (MUNT), MP3CUE, Overscan border, Stereo-swap, SDL_Resize, MemSize128, Internal 3dfx voodoo chip emulation, Amstrad & PS/1 sound emulation, Fluidsynth soundfont support, Timidity++ backend support, CGA w/ Monochrome Monitor Support, Improve PC Speaker emulation accuracy patch, etc.

It allows redirecting LPT1 (through LPT3) to an actual LPT port, a printer file (.prn), or to the virtual printer.

If you set it up to send to the virtual printer, it can "print" to a graphic file (.PNG, .BMP, .PS), or to a Windows printer on the host (it pops up Windows a print dialog):

DOSBox Printing

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I somehow doubt that proper emulation of the parallel port was a priority for the DosBox devs.

Id did find this patch someone wrote in 2006:

http://vogons.zetafleet.com/viewtopic.php?t=13117

which links to what is apparently a DosBox fork support forum?

http://qv90.hopto.org/bb/viewforum.php?f=3

Depending on how bad you want this, honestly, your best option might be getting older hardware and running DOS natively on it.

Alternately you might try running it in a true virtual machine like VirtualBox, VMWare, Xen, Virtual PC, etc.

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Use WinPrint for this:

Takes standard printer output produced by a DOS application, and forwards it to a default Windows printer. Converts code page, strips empty pages, supports BOX DRAWINGS chars. Works on all Windows platforms. Written in Borland DELPHI.

It's specifically designed to help you print from old DOS programs onto new, USB connected printers.

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