A lot of this sounds like they were under-resourced and the business increasingly adopted new technology with no ongoing support for their IT infrastructure. > These legacy systems will in many cases need to be migrated to new versions, substantially modified, or even rebuilt from the ground up, either because they are unsupported and therefore cannot be repurchased or restored, or because they simply will not operat…
While I'm certain they are underfunded and overworked, this sounds like they had an internet accessible terminal server. I'd like to imagine IT screaming this is a bad idea but a suit somewhere saying they needed easy access for partners. I can only imagine how insecure the solution they replaced with this one was.