After all that, he was only getting two encrypted emails a year! Damn. That's crazy.
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The concept of software distribution being a tar.gz.gpg or verifiable md5 file is obsolete.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.