Here's some items not as yet on the "rough list of concrete stuff" AFAICT, which
perhaps should be, at least from a completeness perspective (YMMV)...
Background/Requirements/Opportunities..
Adam Langley, 2009, W2SP. "Opportunistic Encryption Everywhere". W2SP.
http://w2spconf.com/2009/papers/s1p2.pdf
Andrea Bittau, et al. (2010-08-13). "The case for ubiquitous transport-level
encryption". 19th USENIX Security Symposium.
http://www.usenix.org/events/sec10/tech/full_papers/Bittau.pdf
Opportunistic encryption (has list of various applicable projects)
http://en.wikipedia.org/wiki/Opportunistic_encryption
Linux FreeS/WAN Project - Opportunistic Encryption
Henry Spencer, D. Hugh Redelmeier.
http://www.freeswan.org/freeswan_trees/freeswan-1.91/doc/opportunism.spec
examples..
tcpcrypt
http://en.wikipedia.org/wiki/Tcpcrypt
https://tools.ietf.org/html/draft-bittau-tcp-crypt-03
Obfuscated TCP
http://en.wikipedia.org/wiki/Obfuscated_TCP
[tcpm] Faster application handshakes with SYN/ACK payloads
http://www.ietf.org/mail-archive/web/tcpm/current/msg03829.html
http://tools.ietf.org/html/draft-agl-tcpm-sadata-01
IETF rejects Obfuscated TCP (email thread on tcpm@)
http://comments.gmane.org/gmane.network.peer-to-peer.p2p-hackers/2099
freeS/WAN, Openswan, Libreswan et al.
http://en.wikipedia.org/wiki/FreeS/WAN
HTH,
=JeffH
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