Personally I'd make a distinction between mail transmitted through a third party and mail stored by a third party. When I send mail, the mailservers in the middle have to make a copy of it to store and forward it, but the expectation is that they only hold that copy long enough to do their job and then delete it. When my mail's hosted by Google, though, it's somewhat different in that I expect Google to hold it indefinitely and to have access to it that's not under my control. IMO there should be a difference in what you can expect between the two as far as privacy goes.

Attorney-client privilege should be an analogy lawyers and judges can relate to. If a lawyer packages up documents in a sealed envelope and uses FedEx to deliver them to his client, privilege wouldn't be considered waived. When the attorney or his client brings an uninvolved third party into the room while they're discussing things, though, or gives them copies of the documents to hold, that's a completely different matter.

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