Was wondering if anyone actually knew how HTB retires a machine? I thought they were retired oldest first but Tentacle is replacing Compromised on Saturday so now I’m not sure.
It is generally the oldest but not always - Rope2 was active for about 6 months while other boxes got retired.
As far as I can see, it is down to the balance of boxes between OSes etc. It is nearly always one of the four oldest boxes to go.
If you check Login :: Hack The Box :: Penetration Testing Labs you can see which ones have been accepted so you can at least ball-park guess the next box to retire.
The accepted list has an easy, insane and medium box as accepted, so at a guess, I’d go for Worker being the next to retire.
However - and this is a huge caveat - it is also driven by a range of operational reasons within HTB, so it really is guess work and a magic-8 ball is probably as accurate as anything I’d suggest.
Makes sense. I assume they want to keep the difficulty of machines somewhat wide since having mostly hard/insane machines would most likely put new-free users off from the whole thing due to frustration.
I do like the idea of them just asking a magic 8 ball important questions though.
I feel like my entire life revolves around magic 8 ball decisions…
I sent Shaun a message and its based on the following metrics:
Machine Retirement:
- Age of the Machine
- Difficulty
- Ratings
- Balance between Linux and Windows
A mixture of all the above
So magic 8 ball then 
“Signs point to yes”