1. that establishing and maintaining (with limited key lifetimes and handling key revocations etc.) the preferred web of trust PKI model it implements is too much work for this to be adopted by more than a few people, and
2. too few people can use secret keys in simple and standard pocketable hardware which treats the complex host computer as part of the untrusted network rather than as something ever likely to be secured adequately by the end user.
So as far as the 1990ies implementation environment in which this crypto security dream started is concerned, dream on.
However, DNSSEC will probably go a long way to solving the PKI issue. There are enough people handing domain rollover and getting/renewing a certificate at the same time as you register or renew a domain kills 2 birds with one stone. But we will then still need a simpler lightweight pocketable device for secret key storage and computations and which can at least make visible what you are signing and decrypting. I think for most people this is more likely to be their mobile phone than their desktop or laptop computer.
Possibly ways to start improving this might be to implement GPG as an Android application which accesses a DNSSEC trust anchor domain somewhere and which enables users to register signed subdomains. However, we'll probably see Android getting almost as bad from a security perspective as Windows before long, when having an internally hardware secured phone subsystem for this purpose will start to make sense.
It would be useful to have a cheap automatic registration DNSSEC subdomain trust anchor for developers and ones where they check your ID credentials more carefully and which charges you for a certificate. Different trust anchor CA policies will lead to different levels of confidence in identity, but all can give better assurances that email@example.com is the genuine user of that address than current GPG usage suggests.
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