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I'm not familiar with windows parental controls/family safety or Disney Circle so I can't help trouble shoot at that end, but I might be able to help point you to a solution.
What capacity does Disney Circle function in? Does it just block websites or can it block suspicious exes? You said Portal 2 is installed but does not open. If either of your blocker thing a majigs only likes "trusted" exes to be opened, it might not be familiar with Portal 2.
seems like you have a spaghetti tangle of parental controls with computers... you might wanna try stripping away all the controls and reinstall them one at a time until you figure out what is blocking Portal 2 from opening. If it says Windows Parental Controls, it's probably not Disney Circle. Try looking through all your windows settings or just plain googling about windows parental controls blocking a program from opening.
Sorry that wasn't very helpful but its a start.
I'm almost tempted to wipe his laptop and start over with a clean machine. Its already had the hardrive replaced about three months ago so there's not much to back up. Thanks anyway! :)
Can other files/games be downloaded or does only Portal 2 get blocked? If you haven't, try other steam games or non-steam exes.