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How to support PGP encryption in Gmail

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Re: How to support PGP encryption in Gmail

#41
post #38

Earlier quoted context omitted.

One thing that is currently missing from E2E (as far as I can tell having played with it a little in the last month) is any kind of web of trust. When I import a key, I can't tell if it has been signed by me or someone I trust. Is this on the radar for the UI after the Keyring reimplementation is finished? At the moment, what we've suggested at our work is that people manage keys in GPG and then only export keys into…

See https://github.com/google/end-to-end/wiki/Key-Distribution . In short, we don't invest much into WoT.

After giving that a read, I'm happy that there are people way smarter than me working on these problems. Kudos to your efforts!

Re: How to support PGP encryption in Gmail

#42
post #8

What is so terrible for people about using an email client? I find using the Gmail web interface to be frustrating because they've removed the ability to pop out the compose view into it's own window, so I can't easily reference information in another browser tab while writing an email for instance. Meanwhile, Gmail has excellent IMAP support, which lets me use Thunderbird + Enigmail to get excellent PGP support.

You can shift-click the "full screen" button on the compose window to pop it out into a separate window. There is a tool tip that appears if you hover over it.

Re: How to support PGP encryption in Gmail

#45
post #8

What is so terrible for people about using an email client? I find using the Gmail web interface to be frustrating because they've removed the ability to pop out the compose view into it's own window, so I can't easily reference information in another browser tab while writing an email for instance. Meanwhile, Gmail has excellent IMAP support, which lets me use Thunderbird + Enigmail to get excellent PGP support.

Nothing. Except Thunderbird+Enigmail is not something that is going to appeal to the masses. Web-based mail came along and all of a sudden it didn't matter where you were in the world, you could log in and check your email from any computer.

Encryption means nothing unless both parties are using using it (obviously), and if it's only a few users who are encrypting emails using Thunderbird+Enigmail then there's that "why are you encrypting, you must have something to hide" and so the theory goes that you are more likely to catch the eye of big brother who then keeps a closer eye on you... if everyone is encrypting everything then we are all on the same footing.

Unfortunately things need to be made easy for the masses to adopt, like the way iMessages works, which is seemless. I don't want to worry about which pgp server upload my key, or having to go to 10 different places to revoke my key.

BUT, I don't trust any web-based encryption either since it's liable to be tampered with: https://en.wikipedia.org/wiki/Hushmail

Thunderbird+Enigmail is the safer way to go in general (and is actually what i use also).

Re: How to support PGP encryption in Gmail

#48
post #27

It's worth mentioning Mailvelope ( https://www.mailvelope.com/ ) - Free - Supported in FF / Chrome - Supports Gmail, Yahoo, Outlook and GMX I've been using it extensively for about 12 months now. It's solid, unobtrustive, and just .. works. Decryption of attachments would be nice, but it's definitely not a deal breaker.

FWIW Mailvelope also works fine with Fastmail in my experience.

Re: How to support PGP encryption in Gmail

#49
post #25
post #22

Earlier quoted context omitted.

You're correct, and I think this is part of the growing disgruntling about PGP. The most successful deployment, Debian, is a closed system : while Debian developers' keys and signatures are on the standard public keyservers, for Debian membership and archive authentication purposes, only signatures from existing Debian members count, and only keys explicitly pushed to Debian servers are usable. So it is possible for…

Huh, I didn't know about the Debian rules. But Debian keys and signatures are published to public keyservers too, aren't they? So your trust paths that contain a Debian developer may not guarantee the trustworthiness of the endpoint. I thought that bootstrapping my trust from one of the Debian developers would make sense, since I already have Debian installed (somewhere you have to start). Looks like it's not that a…

Yeah, a trust path that is end-to-end all Debian developers is fine. And I sometimes know that a certain human (that I don't have a way to meet with in person) is a reasonable human being, so I'll trust a path to that human that consists of Debian people, or other people I personally know to be reasonable human beings.

Re: How to support PGP encryption in Gmail

#50

Earlier quoted context omitted.

"Signing a key" really means signing the binding of a uid to a public/private key pair. I had to look at the Open PGP spec to figure that out ;-) The question is, how to do verify that a particular person is exclusive owner of a uid? Because the uid is just a piece of text, there is no general way that will work every time. It depends on what the uid is. Someone could put their Passport number in the uid and you coul…

> But if you are actually concerned about the identity of the person, passport numbers, etc are better uids. Why not just name + email? I don't think putting anything like a passport number is a wise idea. It's just putting one more semi-secret information on the internet. I think the encryption and signing+trust gets mixed here. If I know someone only by email address, I don't trust their key very much. But I'm stil…

The point is that the uid is just a string. You can put anything you want in it. Most people put their name + email because that's what is useful for most internet transactions. If you get an email from someone, you want to be able to verify that it is from the person who controls that email account.

For example, I work in Japan. My colleagues work in the UK. Generally speaking I know who they are because I work with them every day. However, I have never checked their real life credentials, because it doesn't matter to me. When I receive an email from them, all I am interested in is "Is this Joe Blow that I work with from the UK". I don't care if Joe Blow is their real name, or if their carefully cultivated story of growing up in Shouthampton and going to the London School of Economics is true (as opposed to growing up as an indentured clown in a travelling circus and escaping at the age of 14 on the back of an elephant). When I receive an email from them, none of that matters. I just care if it's the same person I worked with.

So most of the time people put their email address and a name (which may or may not be fictional). When I sign that uid against a key I am saying, "I verify that this person controls this email address and is the person I know as Joe Blow".

If you actually care about whether the person is who they say they are, then the uid is going to have to contain something more identifiable/verifiable. So for instance, let's suppose I'm a bank. I want to verify that orders coming from my customers are really from that person. It is important that it is really that person because there are laws about identifying where bank transactions originate. I don't care which email addresses they control. I don't care if they are spoofing their email address. What I care about is that any messages I receive from them are really from them (and that any encrypted messages I send to them is really only readable by them).

So a passport number would be a good solution. The person walks into a bank with a USB key containing their public key with a passport number uid on it. The bank physically checks their passport to see that it matches and that it does, indeed, belong to the person who claims that it does. It then signs that uid against the key and locks it away somewhere. The key never has to be on the internet. Why would it? Nobody on the internet cares who you really are (apart from the NSA, I guess). They only care that you are the person who owns a particular email address.

I agree that there is a lot of confusion over encryption, signing, trust and identity verification. To a large part, I blame the convoluted nature of Open PGP and the existing documentation which conflates many, many issues.

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