Hey, been using Glasswire for a few months~
Got Basic a few weeks ago.
I had been away from my pc for 2 weeks (it was turned off) (unrelated), and when i came back, i had no internet (Chrome suspected Firewall blockage) Windows (10) was conflicting, sometimes saying it was all fine, sometimes saying it cant find the problem, But the most notable error was when it said a firewall rule named glasswire_randomnumbers (something) was blocking access to the Internet.
So, i checked the rules it had created (i had “ask to connect” on) and it had indeed blocked “Host process for windows services” (svchost.exe) even if the service/file was allowed (a minumum) 5 (duplicates) times before.
I guess it creates a new rule for the service/file every time it changes (windows updates i suppose)
Anyway, to the real problem: the next restart the firewall was turned off. (Glasswire’s, not window’s) and “ask to connect” was reset to “click to block”.
If i tried to click “on” it will stay on for 5sec -1 minute before automatically turning off again.
I did google around a bit, and found out if you turn off windows firewall, and turn it back on with Glasswire i.imgur.com/Vdf4d3X.png the problem is fixed until you restart the pc again. (Credits to whoever it was, thx.)
I tried to upgrade Glasswire to the last version, 1.1.39b from… well, the one before that one. 
It did not fix the problem. On my google trip i saw that multiple users have this problem, and a fix to this (well, critical program breaking) bug will have been nice.
My last option is a clean install, but since that erases my history, i will not do that just yet, i will give you some time to fix it.
My (random) guess is that windows blocks Glasswire somehow, making Glasswire turn itself off. Since it thinks it (tried) to block the (now fixed) internet connection. (if thats even possible.)
Windows 10 64bit. Glasswire Basic 1.1.39b. Sorry for any typos, thx for any help.
-kk2