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I am looking for (preferably freeware/opensource) Windows (XP/Vista) based application which allows files to be transferred across two computers through their parallel ports, something like Hyperterminal, except for parallel ports.

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Which version of windows? There is native support in the DOS based windows through interlink or direct connect but I assume you are trying to do this on a xp or later system... –  Kyle Jul 27 '11 at 1:46
    
Do you have a null modem cable? If so, you can create an incoming connection in Network Connections on the LPT port, then create a connection TO the computer on the second one –  Canadian Luke Jul 27 '11 at 5:54

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