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After I get there. I have a desktop PC, not a laptop. I can't really leave it on and then head over. Unless what you're implying is that I need "activate" offline mode on my computer by using it when I'm online here? If so, I really wish Valve would make that much clearer than the infuriating error that pops up now when I try to use offline mode while offline.

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Yes, the prescribed way is putting it into offline mode before you lose the connection. It sometimes lets you go into offline without a connection but I don't understand the method it uses to make that decision.

Yeah, if I'm headed to my cottage or some place without Internet access I make sure whatever games I want to play are updated then I switch to offline mode.

Sometimes I can go straight to offline mode but to be on the safe side, switch before you lose network access.

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