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Has this been challenged yet in a court, when someone reading only the right-hand column decides they feel all lawsuity? Is this sort of 'user-friendly interface' covered by existing case law?

IANAL either, and I wouldn't touch this or anything else that hadn't been vetted by a professional. To me, on first glance, this smells like class-action bait. "Your Honor, the defendants deliberately misled the plaintiffs by placing a 'simple' Terms of Service on their website, but then hid their true intentions in small print which claimed the obvious, prominent version wasn't legally binding." Who needs that hassle?

I'm not a lawyer, but I have been through the process of litigating a contract in court.

The law does cover this. Contracts are about a meeting of the minds. Do both parties understand and agree to the terms. Things like email, other written communication about the contract or terms are all reviewed at trial. It's amazing how much of the "sneaky" verbage just get thrown out or ignored as unreasonable or not understood.

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