Parallel port for hardware key

It might be possible to use a converter cable USB-to-Parallel (Make sure you get an Parallel connector and not Centronics)
This is a example: https://www.lindy.co.uk/usb-firewire-c4/usb-converters-c213/usb-to-parallel-printer-port-adapter-cable-1-5m-p485

It might be better, if possible, to contact your software supplier, to see if there is an USB replacement for the hardware key.

It is not likely to work with the adapter. We tried that a long time ago and in our case, it did not work. The software vendor had to change their approach.

Parallel ports died about a decade ago. Have you contacted your supplier for a different approach?

Agreed.

USB to Parallel adapter is designed for printer only.

About a decade ago, I had a all-in-one printer which could do scanning. USB to Parallel adapter will never do anything else other than printing.

"For use with Parallel printers only - does not support any other parallel devices"

The above details are from the product suggested by the member who posted the first comment.

Besides, serial to parallel converter will not help you as the use case for such converter is for digital clock only.

Must be pretty old software if it has a parallel port dongle. a PCMCIA parallel port dongle might work if the software vendor has no other workaround.