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Let's think about this more closely.

Where are you hosting your email. Are you keeping it on say an AWS instance? OK flag that, all the plaintext would be there, and also, duh, it's still obvious that it's your communication because you're connecting to it, and maybe even paying for it.

OK, you host it at home on your DSL line? OK, so plaintext is harder, but oh wait. Yeah, your IP.

TOR hidden service or something? Good luck getting SMTP to work over tor.

So tell me again how TLS is going to help with metadata.



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