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[RESOLVED]Updating in C:\srcds\orangebox
I ran hldsupdatetool -command update -game "TF" -dir C:\srcds

And now it keeps going

No installation found at C:\srcds/orangebox
Retrying in 30 seconds...

It finally said

Checking/installing Team Fortress 2...

But then went back to

Retrying in 30 seconds...


Edit: Patience is a virtue.
Is that the only game that you have in the directory? Also make sure you do not have a firewall or anything like that blocking it from running.
Game Servers -- -- Use promocode "frag" for 15% off every month!
Was that your original install command?
~ trewq

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