Good article. I wonder why Mailpile are targeting difficult use-cases such as activists, journalists, etc. It feels like every PGP provider aims for this, but OTR encryption tools aim for a much easier use case: average users who just want to hide their private conversations from big data algorithms which then sell their secrets publicly. OTR is much easier as a result, but it can't do email (that I know of). :-(

In this article mailpile worry about users who need an airgap. What worries me is whether creating features for airgap users makes anti-features for users like me who just use PGP when mailing with my parents, my wife, and some friends. We just want to avoid our secrets being part of "Big Data" and as a side benefit we resist passive surveillance. Mailvelope (which is "easy") is complicated enough for my parents, they would never add the complexity of an airgap. We just want easy encryption, even if it isn't totally NSA-proof.