After all that, he was only getting two encrypted emails a year! Damn. That's crazy.
One day however, my bank started offering transaction notifications by email, with optional PGP encryption. Suddenly there was real utility, and without any trace of WoT issues (key exchange over the same web frontend already trusted for actually transferring money, and the key in question is only for read-only messages). Other than that, the only encrypted messages I receive are the ones I send to myself as a convenient (because everything is already set up) form of secure cloud storage.
I see the two problems being "People don't bother with the clunkiness of using PGP when sending an email about what to pick up from the store" and "most users have no reason to talk to most other users".
I'm considering making it a point to message people with interesting Keybase avatars or social profiles tied to their Keybase if only to have an excuse to use PGP more, as silly as that might sound.
As far as I know they are working on a messaging app as well.
On the other hand, perhaps the argument for this would be a "trusted 3rd party" model (a la S/MIME).
Rather every device has a new key, and they all sign each other. You can add new devices without old proves being invalidated.
See: https://keybase.io/blog/keybase-new-key-model and https://saltpack.org/
I would really like a solution using this stuff that is highly integrated with my mail client.
Additionally, and I realize this is tangential to this discussion, I use pseudonyms to somewhat reduce my privacy "surface", so to speak. If I take my twitter, HN, reddit, etc, etc. and say "this is me", you could build a pretty decent profile of who I am (politics, hobbies, profession, where I live and so on). That's a different privacy problem than keybase is trying to solve, so no criticism is intended, but it is a problem for me.
I use KB as an easy way for people to verify my signed messages - not necessarily for sending encrypted messages to other users. Mostly just a "This is me, you can verify it is me at Keybase easily - as long as you trust Keybase."
Doing that means users don't need to install PGP and know how to use it to verify that I am me. It isn't important now - or hopefully ever. By making a practice of it, my users expect it. if I am ever compromised, the malicious actor won't succeed in fooling my users as I expect at least a few will try and verify the message and will see it doesn't verify.
For myself, it's about being a solution for a "what if?" scenario than anything practical or even privacy-related. It's just the best psuedonymous way of proving identity within some level of reasonable doubt that I know of.
The concept of a git repo means I don't need to sign anything, I'll just roll back if I pull the wrong thing. Socialization at work hasn't atomized enough that my only human contact with a coworker would be a gpg signed commit anyway.
The concept of software distribution being a tar.gz.gpg or verifiable md5 file is obsolete. Behind the scenes something like apt-get does sign things but how to integrate its list of keys with the end user is a mystery, its essentially magic. Besides it provides no security due to lack of MITM attacks in practice.
Can't use weak OS unless its behind a firewall and/or accessed thru the VPN at which case plain text is about as strong as the weak OS and the VPN or physical LAN security is "good enough". So plain text files on a networked fileserver perhaps relying on login and permissions but mostly on audits and fire anyone who does something naughty.
Everyone needs version control no one understands it but some (repeat, some) devs. The office workers have a similar relationship with encryption. Also with databases, given that the corporate standard database is Excel. Talk till you're blue in the face, it will change nothing. Good idea, not good here. If you think office workers need encryption, you're probably wrong, but it doesn't matter because they definitely won't listen anyway. They're too busy making closed siloed databases with Excel.
Can't use GPG to encrypt web traffic, there's a whole SSL https infrastructure for that. The cloud resource can be assumed to be completely government(s) (and hacker) penetrated at all times. Just a business decision to tolerate that. I could use encryption and signing to make sure the traffic isn't interfered with before the NSA logs their plain text version for all time, but why make their jobs easier?
Theft by monitoring data streaming along has pragmatically never been an issue, its always someone stealing entire (copied) mass storage units at a time or violating some higher level business protocol of "look don't touch" or even "don't touch" but its all plain text for various business reasons. So encrypting transmissions is a waste of time, VPN exists more for AAA not to prevent monitoring. Multiple governments and corporations have full access to both endpoints anyway.
Email is mostly (exclusively?) used for public mailing lists, and corporate receipt/alert traffic, none of which is benefited by encryption. Its been awhile since I had an old fashioned email conversation on email. Everyone loves texting and messaging none of which can use encryption usefully.
Anyone with physical access to the device can pown it completely, theres no point in a purely software solution you're just wasting time.
Very few people had an application in business or real life in say 1970 for nuclear grade encryption. Nothing has changed to 2017 other than its trivial to provide if someone needs it. Many people want it because its cool but it does nothing useful for them so its definitely a want not need.
The very first bootstrap is impossible to do securely in the general case short of building a computer from scratch, but you can do things that make it difficult to attack e.g. ask a bunch of different friends what the sha1sum of the latest debian release should be.
On the assumption that you manage to get a non-compromised version of debian installed you are secure even against MitM attacks; there's a chain of trust, every package has been signed by a key that has a key fingerprint claimed by a specific human maintainer, and new maintainers can only join after at least one maintainer has confirmed their identity against a government-issue document. Of course this doesn't make attacks impossible (e.g. rubber-hoses against one of the maintainers), but it makes the cost a lot higher.
I'm kidding but I'm also serious.