[zenexer]

Option 6 seems like the most viable to me, but it's still a long shot. If they wanted to upgrade, they would've done that a long time ago. At the end of the day, they don't want to upgrade. I'm sure they could get software that does the same thing that runs on newer platforms if they cared enough.

[Azeralthefallen]

Afaik they cannot upgrade because they are heavily reliant on a specialized piece of software that:

1. Requires a dongle attached to a parallel port for it to function. 2. The company who made it went out of business over 15 years ago.

They have plans in the future to migrate to linux, but that isn't in the card for a few years unfortunately.

[zenexer]

If the dongle is for licensing:

1. You probably don't need it. I don't know about the legalities involved here or what the specific license is, but there's probably a trivial way to circumvent the hardware requirement, especially with a VM. Back when Windows 2000 was a thing, people were still using MD5, and nobody was using secure elements. Worst case scenario, they've got some of the actual program logic on there, and you'll have to either reverse it or replace it. Again, not commenting on the legalities here, but seeing how the software was (presumably) legally licensed and the company is long gone, it couldn't hurt to ask the lawyers whether they think it's safe.

2. You can pass a parallel port through to a VM if you really must.

[etaioinshrdlu]

Off topic, but .... Wow ... technical debt anyone?