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Making PGP Key Management Invisible So Johnny Can Encrypt

blog.whiteout.io

1–10 of 78 posts

Re: Making PGP Key Management Invisible So Johnny Can Encrypt

#2
Or just use S/MIME which is baked into most email clients? Of course, handing out keys is an issue, but in the world of social media why not just attach one's key to one's public profile? Facebook, linkedin, etc. Not sure why S/MIME doesn't get any love. It works, its the most common email encryption scheme, and typically you don't need a third party application or command-line-fu to get it to work. I've seen the dimmest of office workers deal with it everyday.

Re: Making PGP Key Management Invisible So Johnny Can Encrypt

#3
I think the 99% of the time it's not an issue argument is invalid. Encryption isn't really necessary for 99% of people at any given time anyways. It's just that you don't know when you're in the 99 and when you're in the 1 percent, and a mistake in that 1 percent of the time is crucial, that's why we try to do it 100% of the time.

Re: Making PGP Key Management Invisible So Johnny Can Encrypt

#5
In my experience, key distribution is the easiest thing about PGP / GPG. EnigMail and most other clients can already query key servers easily. Enigmail routinely asks me to "download missing keys", and if my recipient's key is on a keyserver, it downloads them. In fact, the PGP global directory (https://keyserver.pgp.com/vkd/GetWelcomeScreen.event) already seems to have all the features that are missing from the whiteout server (SSL, scalability, e-mail validation, etc).

The biggest adoption problem around key management that I see is getting people to generate them securely, then integrating the keys across multiple devices and multiple clients. Maybe this whiteout mail app thing is supposed to be the part of this that makes key management "invisible", but I don't see why they can't use the existing key distribution infrastructure.

Re: Making PGP Key Management Invisible So Johnny Can Encrypt

#7
I think this makes a lot of sense, but:

> Even with automatic key lookup, users can later always navigate to the contacts menu and verify a recipient’s key fingerprint if they need to.

Okay, how about making this (optional step) way easier too. Show the fingerprint somewhere on-screen everytime you send a message. (Maybe flagged for extra notice the first time the key is imported?)

Maybe with a little (i) icon next to the fingerprint, clicking on it explains what it is, and how for top confidence the fingerprint should be checked with the owner directly.

A good UI makes it easy for the unsophisticated, but provides cues to give the user an easy and gradual path to being more sophisticated too (and makes being more sophisticated as easy as possible too).

Re: Making PGP Key Management Invisible So Johnny Can Encrypt

#8

Or just use S/MIME which is baked into most email clients? Of course, handing out keys is an issue, but in the world of social media why not just attach one's key to one's public profile? Facebook, linkedin, etc. Not sure why S/MIME doesn't get any love. It works, its the most common email encryption scheme, and typically you don't need a third party application or command-line-fu to get it to work. I've seen the dim…

>why not just attach one's key to one's public profile?

This is equally valid for PGP keys, and a common practice among the security conscious.

Re: Making PGP Key Management Invisible So Johnny Can Encrypt

#10

I think this makes a lot of sense, but: > Even with automatic key lookup, users can later always navigate to the contacts menu and verify a recipient’s key fingerprint if they need to. Okay, how about making this (optional step) way easier too. Show the fingerprint somewhere on-screen everytime you send a message. (Maybe flagged for extra notice the first time the key is imported?) Maybe with a little (i) icon next t…

Rendering the fingerprint as an image (a'la github's default portraits) would help; we can more easily see differences in images than we can strings of numbers.
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