Very good advise above, but I would like to add: be very, very careful how you word your report. Don't use words like "illegal" and "gray zone". The software was mismanaged, fixing it is going to cost a lot of money and there is an illegal situation. Most managers do not like to hear this and above all they don''t want this in writing.
Write that you have software for which the licenses are running out very soon, and some for which the licenses are unclear.
Give an inventory and detailed recommendations. Spread out the costs as much as possible and make sure to mention the extra benefits like support and updated versions. Sweeten the pill as much as possible.
Explain verbally that there are cases where there are no licenses at all, and that can get the company in trouble.

I still write cursive because it's much faster than block letters. If you put some effort in (practicing a bit), it looks better as well.

I have a friend who is a decent guitar player (or whatever it is called when people sit around a campfire listening to your music). He did invest quite a bit of time to be a decent player. Yet what did he learn? To play an instrument. Not to play a game. I'm fairly sure, the same time he spent on practicing playing guitar would have made him a Guitar Hero master. While it might be annoying to turn around a question like that I think it illustrates my point very well. Both are fun things to do, neither train essential life skills. Guitar hero is not a simulation of playing guitar, it's a game based on it. You are not asking why people are playing whack a mole instead of hunting moles in real life either. Or playing Mario instead of doing real athletics?