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ask them to connect to arbitrary hosts. There are still a lot of those

Yep, I get that and I understand the problem you're describing is an actual problem. I just don't think 'endpoint hands over its plaintext' is the right solution.

I would definitely like to be able to sniff Dropbox and see what it's sending

Well, I'm sure you can, it's just not as easy as firing up tcpdump. But if you wanted to you could, it probably won't even take you long. 'It's not as convenient as firing up tcpdump' is still not a strong argument for 'just hand over the plaintext', in my mind.

I'll wrap this up with a story you might have also seen play out over twitter the last couple of months. Tavis Ormandy, a security engineer currently working on Project Zero at Google has been dissecting various AV products and finding them riddled with pervasive and gross security holes up to and including intercepting TLS traffic and then screwing it up so badly as to make it highly vulnerable.

The response from one vocal AV expert has been 'well, we wouldn't have to do that [and screw it up] if you gave us a tap/API into the plaintext so we can keep you all safe'. The predictable retort of security engineers has been 'LOL, NO'. I think ultimately, that 'LOL, NO' is what you're up against rather than some rando ranting at you on a message board. Enjoyable as it has been!



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