Earlier quoted context omitted.
Well your point F nullifies your point about A-D does it not? As for a second point F, the identity can be derived from the unencrypted headers in PGP. Before PGP: From: bob@alqaeda.org To: bill@gmail.com Subject: The snow this year is better at Innsbrook. But not at St. Moritz. After PGP: From: bob@alqaeda.org To: bill@gmail.com Mime-shit.... DEFKJiwfou3hoqwdnhoqiwfhoqifowqihwqoidhqwod== PGP is an encapsulation and…
No, it does not. Take this message: From: anonymous_acct_101@mailpile.is To: anonymous_acct_77@mailpile.is Mime-shit.... DEFKJiwfou3hoqwdnhoqiwfhoqifowqihwqoidhqwod== This is quite a secure message and it would be as easy to send as any other email with mailpile or similar services. My point is that security is not a black&white concept. There is a continuous of security, and part of the job of mailpile could be to g…
If Mailpile is the MTA, and the NSA is following the connections to Mailpile's servers they can use time correlation to find out the metadata.
Metadata is hard to hide^.
Anyway, as the other posted mentioned, the correct solution is definitely full security across the board, with full encryption MTA->MTA. That needs to happen so it can't be sniffed on the wire. But of course full security between Alice's MTA and Bob's MTA is ultimately pointless when Bob's MTA (e.g. Gmail) is sleeping with Evan (the NSA).
The actual message contents need to be decrypted with keys that only the recipient has access to, and GPG is as good a solution as any for that. You can only trust what only you have. Don't trust Google. Don't trust Mailpile, either.
^ anon.penet.fi was an OK solution, but still was subject to possible timing attacks (and legal attacks since a table exists SOMEWHERE in the universe that correlates your name to your nym).
A nym.alias.net solution is better when you're chaining remailers and using random timing delays.
Deadrops are better, post your message anonymously to a newsgroup/forum/etc via a Tor or other anonymous connection, and your recipient does the same to retrieve the message anonymous. There's no metadata there to capture.