@psa 's video link in post #1 mentions Linked In working with Microsoft to snoop for installed software apps.
I can confirm that one of the tasks performed during Microsoft Updates is to search the C:\ drive to look for specific installed software which is not registered, and anything on the list is disabled.
This isn't 'tin foil hat' conspiracy theory beliefs. In Windows XP, the update.log file could be opened and read with notepad, and most of it was in plain English. There was a list of specific software which the update searched for, so most likely certain copyright holders pay a fee to Microsoft to do this on their behalf.
I make computer fonts as a hobby, and I have a collection of more than 250,000 fonts. Many of them are commercial fonts which should only be available by purchase, but I didn't buy any of them. I don't think any of them are installed, and none are saved on the C:\ drive. I have them only because I hoard stuff, and sometimes I look at them with a font editor to study the vector construction.
I make fonts with a font editor named ScanFont3. It was created around 1995, it's no longer sold, and it won't work with any Windows operating system more recent than XP. The cracked version I have also won't work after a Windows Update from January, 2014.
I got around that problem by having my geek install Windows XP on a few laptops where he first formatted the hard drives then installed XP and service packs 1, 2 and 3 only. Those computers have never been connected to the Internet since the operating systems were installed - I move data with a USB drive. People using the latest and most expensive font editing software cannot reproduce some of my results.