I am using Windows 10, latest version, Adobe PDF Pack, paid up, latest version.
I have attached screenshots for all steps as described.
When opening a pdf on laptop (laptop shot), and pressing the "pdf compress" icon (laptop2 shot), it takes me to the web page for compress. BUT(bug) it will not perform the compress but rather asks me to upgrade (or free trail). (web shot1)
This applied to all pdf documents on my laptop, not just a specific file.
If I log directly onto my Adobe web home page, select compress (web shot2), then drag/drop a pdf from my laptop, it works fine.
So the bug sits with the link between the laptop icon and the web page it takes me to - that web page doesn't pick up my account status (pdf pack). It should take me to the compress page on my web account.
My account details fyi (web shot3)