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Well, I may not be an expert on CS:S Servers, as I mess with TF2 Servers, but I can assure you that the proccess is the same. Whenever you see that the server is out of date, just go to steamCMD and follow the same process that you would when you installed the server in the first place. When SteamCMD detects that you have already gotten the files in that directory, then it will just provide the neccessary updates.
If you are still confused, I have a tutorial series on this forum on how to create a TF2 Server, but just follow the First 3 videos, as those mainly mess with the SteamCMD and updating (as well as auto-scripting!).
Well, I hope that helps, just make sure your force_install_dir is the same as the server you are trying to update.
Alright, I just mentioned the check because maybe you have 2 servers on your computer you don't know about, so maybe you can search for "srcds.exe" on your entire computer?
Don't know, just throwing out ideas.
Did it work?