Well, it seems like valve is in the process of breaking another of its games again in this case HL.
My servers have started complaining about that they need an update. So i gave it to them via hldsupdatetool and nothing got updated.
From a little poking around the interwebs i found that this should be related to this breaking of HL that is going on and i found that you should use SteamCMD for server updating.
So the question is should i use this new tool ? I really don't want to break my servers and do them all over again.
Steam Pipe my ass.