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>To eliminate support calls I would simply design a system where any place they went FROM their email would work - maybe up to 3 or 4 links past email.

What? What constitutes a "link"? This doesn't make any sense.

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be on gmail -> click google images picture -> click caption link to small video -> click another youtube video -> ERROR

4 links away from gmail - not allowed. Pretty simple

How are you determining this without sniffing everyone's traffic? How do you know if someone typed youtube.com into their browser window or clicked a link from an email without access to things like referral headers?

this is basically entirely incompatible with SSL

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