A Serial POS device (Card PIN Pad) doesn't work with any Serial-To-USB adapters

I'm asking this as a last resort because I've tried everything I can think of:
I have a 9-pin serial device something like this:
POS Serial Device (Card Reader / PIN Pad)My laptop does not have a Serial-port, only USB ports.
In theory, if i get a Serial-to-USB converter the device should behave *exactly* the same as if it were plugged into a normal Serial/COM port, and, the Windows application that is talking to it will see the virtual COM Port (e.g. COM1) and talk to it *exactly* like it would a normal Serial device.
But I have bought 3 Serial-to-USB converters and only 1 seems like it is able to 'talk' to the device.

There is a catch...
Only this proprietary software that I got from a vendor is able to 'talk' to the device.
It talks just fine on a computer with a built-in serial port,
but it fails on my laptop with a Serial-to-USB converter.

I called the vendor in and they've tried to help, but they are not that tech savvy, and I know others have succeeded with my same software.

Does anybody have any advice or ideas?

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Update:
I should mention, I've tried 3 different converters and 3 different pin-pads and we've changed all the COM port settings to try different COM ports.
With the 1 converter I got, the device 'responds' to commands with the software, but the software still says it can't communicate with the device - and yet if I look at its trace tests in the logs I can indeed see the device is sending responses (only with the 1 converter).
How is it possible that this works just fine on a PC with a built-in COM port, but completely fails on another PC with a converter?
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rfwoolfAsked:
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wolfcamelConnect With a Mentor Commented:
often I have seen this happen because the USB - serial convertor makes the com port something like com15 which the software wont see.
Often the software is also expecting to see it on irq 3 or 5 like a normal serial port.
sometimes you can adjust these settings in device manager and this may help.

more often I have found the need to buy new usb devices
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rfwoolfAuthor Commented:
Very interesting idea about irq 3 or 5... now to investigate how to change those settings..
Thanks for your input!!!
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wolfcamelCommented:
device manager, com port properties, port settings and resources are the things to look at
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rfwoolfAuthor Commented:
It doesn't look like my virtual com port is being listed in the list of IRQ's. Similarly, if I go into the properties of the virtual COM port, i don't see anything about IRQ's.
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JohnnyCanuckConnect With a Mentor Commented:
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