The FBI decides they'd like to read that conversation. They issue a court order requiring you to hand over your TLS private key, and use it to MITM your users to feed them corrupted JS code that discloses PGP private keys.
The small minority of users "detect" this change. But not quickly enough: the whistleblower has already logged in to check their mail, and has now disclosed their private key to the FBI.
What now? What's the feature you're going to build to keep that from happening?
Not only are you using Javascript crypto to provide this "service" to users, but you're not even forward secure.
But decreasing the amount of dragnet surveillance by some extent sounds like a good thing to me. For example, many people wouldn't like the government to know mundane stuff about them, like having an abortion.This could help.
* BTW haven't moxie written about an asynchronous diffie hellman key exchange ? it could at least give PFS to this , so the private key would be much less useful ?
I find it far more dangerous for someone to think they're secure against government level threats, than to know they're not. And if you're not worried about government level threats, gmail with MFA and pinned chrome certs is likely safer than this project. Of course, this is all just my humble opinion...
If the Scramble.io people ship ALL OF THE PROGRAM LOGIC IN THE EXTENSION, it could be secure. But if any program logic (javascript) they interpret is delivered to the user via HTTPS, it will not be secure.
In general, dragnet security will always be possible as long as you can do statistical analysis over both targets in the network (or the whole network), which the NSA has proven it can do.
My point in the previous comment was that dragnet surveillance wouldn't work at all unless the client's code was compromised, but there isn't a good way for the NSA to compromise ALL OR MOST of the clients' code without it being detected by those users who use the extension. Remember the TorMail episode where malicious javascript was injected in the response? If some users had a Firefox extension that checked to make sure that all the JS code was signed by a committee, then they would have raised the flag and alerted everyone not to use TorMail.
Committee depends on things like number of nodes in the network and integrity of the nodes, not to mention you can still do analysis on who was sending or receiving something at a particular time (which may not be enough to stand up in court, but it's enough for the NSA to know that Mike is talking to Jeff, or whomever).
At the end of the day, the best method currently available for clandestine activity on the internet is one-time anonymous drop boxes, and luck.