I haven’t tried to run DOS on Win10, but I haven’t been able to get my old DOS programs to run on anything Windows XP or newer, myself. XP at least had some compatibility options to try. I don’t think I’ve seen those options in Win7 or newer.

It will vary by program, but I’ve needed DosBox on Windows, as well as on Linux, for anything DOS based that I have run anytime recently.

If you can get the organization to switch to Debian, you could do it all with free software and manage the whole thing with Ansible.

I mention this because if the org is running Windows software that old, then current generation FOSS software is going to be a breathe of fresh air, by comparison.

It might not work if someone with a C title has a specific magical Windows package they want.

But even then, I would manage one or two Windows PCs (for a couple of C suite execs) by hand, than a full organization full. And you would save the organization a boatload of money.

Thankfully I was channeling a former employer. I’m glad to be rid of that culture.

Ack! You made me spit my tea, laughing. That’s perfect.

Lots of good replies here so I won’t retread.

I will add that, as a manager, when my team had on-call, I did not mind if my team member wanted to “work” the next day to min/max their compensation; but I sure as hell made sure they didn’t have any production access if they report in sleep deprived.

Name the thing that is so important I must work on it in the morning while sleep-impaired.

The domain controllers aren’t going to apply untested upstream alpha changes to themselves! And tomorrow is Friday, so it’s perfect!