Simple answer to both thoughts is I wouldn't. if we can make it secure enough, can we connect that VM to a shared printer on a different VLAN instead of dedicating one to it, given it's only being used once in a blue moon? Too complex but could reasonably be configured with strict ACL's but that's a little difficult and still potentially leaves security risks if you are unsure of what you're doing. If we can make it secure enough, allow RDP-ing into that VM (with only RDP traffic allowed) I'm pretty sure CVE-2019-0708 would work on Windows Server 2000 and an EOL patch was not released, allowing RCE on that box where a threat actor could easily pull the AD creds of users and further exploit your environment. I would not recommend this. My recommendation is to use Brash/CMR's solution as it will be the simplest to implement. I would advise engaging VMWare support if you are unfamiliar with the VMWare networking management portion. And of course, while I completely understand (been there), I would be remiss if I didn't recommend engaging with your stakeholders to move away from utilizing Windows Server 2000 in production for reasons I'm sure you are well aware of. 😁
... View more