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The problem by doing this is that not all Parallel to USB cables work right out of the box with your equipment.
What you need to do first is make sure that your computer sees the device through the cable. Then when it prompts you for the drivers for the printer install the driver set (parallel) the connection should not matter at this point. However the step of the computer detecting the device first is very important.
You can connect it using a SERIAL NULL MODEM cable, You can download the driver from epsonexpert.com after you register they will send you username and password to login, go to technical resources and select printer model and download the APD304E driver
This definitely sounds like a driver issue because you are able to print a test page so that tells us the computer is successfully communicating with the printer port. What is happening here is the Computer is communicating with the printer through the Operating System (Windows or Apple etc) but the driver IN the software for the POS is not. You didn't mention the computer Operating System you are using or the POS software but the dates of each are ctitical.
The tm-u220d is a high speed printer so make sure you set your LPT1 settings for High Speed Bi Directional printing. (You do this in the Printers Configuration area.)
As far as a driver, check the dates of the driver and look for updates. If you like what I've told you so far then let me know and I'll be glad to assist you further.
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