Great summary Trevor. Two notes to add:

*Apple iMessage, Wickr and BBM Protected can all be described as
opportunistic encryption messaging systems that have been very successful
deployment-wise. Although AFAIK none of them provide any MITM resistance if
the centralized public key servers are compromised or misbehave.

*The general discussion of opportunistic encryption could mention tcpcrypt (
http://tcpcrypt.org/), one of the more ambitious efforts to get this out on
a large scale.
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