I can't get cable or DSL where I am, I'm 1/3 of a mile from the nearest cable box and still can't get comcast to extend the line to our neighborhood!
How about settling on 3Mb/s to all of us instead of 100Mb/s to some and 56Kb/s to the rest of us?
How did the UK force BT to offer these services to everyone and the US can't be bothered?
As an IT contractor I run across this more often than not. All you can do is let the boss know what is going on and give him options.
1) Buy licenses for everything (Unlikely to be affordable at one time)
2) Ignore the problem (Bad idea)
Or the most practical
3) Set up a plan for getting legitimate. If the boss THINKS he has licenses for Windows, suggest that, rather than buy new hardware and reinstall Windows, next time he should buy a PC with it preinstalled. It may take some time but will bring them into line.
Just make sure you put the catch up plan in writing, that way if you ever get audited, you can say the plan is your bosses solution so not your problem, and it shows good faith that you are trying to get current without bankrupting the company.
If all else fails, immortality can always be assured by spectacular error. -- John Kenneth Galbraith