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21 years after the request OpenPGP support gets added to Thunderbird

bugzilla.mozilla.org

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Re: 21 years after the request OpenPGP support gets added to Thunderbird

#141

Post by trishankdatadog »

tptacek wrote: post #134
ifmpx wrote: post #110

Earlier quoted context omitted.

People in this industry use OpenPGP because it's flexible and amendable to almost any usecase you can think of. "Better solutions" are usually indeed better but are also so specialized for their purpose to the point that they can't be easily used for any other purpose. OpenPGP is used to secure everything from simple messages and email to authenticating OS updates for most servers today. Should they use something mor…

It's telling that the most common example of a widespread use of PGP (modern messaging applications exchange more messages in a day than OpenPGP has ever exchanged) is software update schemes, because software update cryptography is both a solved problem (just use signify) and doesn't have network effects; it's a "trust anchor" application. At least with PGP email, you can make the argument that PGP sticks around bec…

> software update cryptography is both a solved problem (just use signify)

Well, just use TUF [1] and in-toto [2] ;)

[1] https://theupdateframework.io/

[2] https://in-toto.io/

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#142

Post by deathgrips »

coderintherye wrote: post #135
hansvm wrote: post #109

Earlier quoted context omitted.

Relevant xkcd: https://xkcd.com/504/

For those that don't click through, it repeats what is a fairly cogent argument. If cryptography is classified as a munition, then there should be legal room to argue we have the right to it as provided by the 2nd amendment.

Congrats, you don't get encrypted because you're not a member of a tightly regulated militia.

Sarcasm aside, the only way to make sure people get encryption is to make it impossible to restrict the technology. That's how encryption ended up spreading. You don't put disruptive tech on every computer on the planet by waiting for permission.

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#143

Post by jolux »

toast0 wrote: post #75
jolux wrote: post #66

Earlier quoted context omitted.

>You can't have strong security guarantees with backwards compatability, because backwards compatability requires plain text sending. That's right. >Unless you're OK with limited guarantees like the UI will tell you when the mail could be sent in plain text. Or if the UI tells you the message will be end to end encrypted, it won't fallback to plain text, etc. This would require changing all the clients.

> This would require changing all the clients. Not really, the old clients would never send (or receive) end to end encrypted messages, so they don't need new UI to tell you that. That's the cost of unbounded backwards comptability. If you want to have 100% coverage of email users, changing all clients is part of the deal. But, uhhh, good luck with that. Server based standards are an easier lift --- you could build a…

>Of course it would be trivial for a hop in the delivery path to subvert that and remove the request, and all hops in delivery would still have message content access; but if people like it, a large majority of servers might support it in 5-10 years.

You're describing TLS, and this is already happening.

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#144

Post by epistasis »

acdha wrote: post #39
epistasis wrote: post #33

Earlier quoted context omitted.

S/MIME is the closest to dead simple solution, but it requires trusting certificate authorities. It's a much better user experience, and honestly I'm surprised that no enterprise orgs have adopted it, because it would probably be cheaper than all this phishing training.

Enterprises, at least in the form of the U.S. federal government, have but there are two key drawbacks: 1. At least until recent, Microsoft implemented it as blocking code in the UI thread – open a message and Outlook won't paint until it can verify the cert, access your local key store (hope your token is in a USB port which is 100% reliable), etc. If you thought “Does that mean that revocation checks block the UI u…

> blocking code in the UI thread – open a message and Outlook won't paint until it can verify the cert

Yikes. I should probably be surprised, but I guess I'm not. This sort of thing goes a long ways towards explaining all sorts of other oddities or using Outlook.

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#145

Post by shp0ngle »

quadrifoliate wrote: post #140
shp0ngle wrote: post #129

"How much do you trust the owner of this key to sign other keys properly? * I don't know * I do NOT trust * I trust marginally * I trust fully * I trust ultimately" This is a real pop-up I got the last time I tried to use PGP with Thunderbird. If people still get regular pop-ups like these, I don't think PGP will ever be popular. They might have switched to PEP (pretty easy privacy) that uses TOFU (trust-on-first-use…

I know it's virtually forbidden to discuss practical details of PGP on HN, but what do you think is the sticking point about that pop-up? It makes people think a little rather than trust blindly, which seems to be...good? I do agree that the marginally and fully options are useless. Wonder if adoption would be better if you just removed them, and were left with: - I don't know what PGP is (exit, opens documentation o…

Even you misunderstood that question.

It's not "how do I trust this person key", but - "how much do I trust this person to sign other people's keys ".

As in "how much do I think that other person is careful in checking other people's keys". Not judging his key, or your ability to check keys. You are judging the other person capability to check another, third person keys.

This is important for PGP "web of trust".

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#146

Post by hprotagonist »

deathgrips wrote: post #142
coderintherye wrote: post #135

Earlier quoted context omitted.

For those that don't click through, it repeats what is a fairly cogent argument. If cryptography is classified as a munition, then there should be legal room to argue we have the right to it as provided by the 2nd amendment.

Congrats, you don't get encrypted because you're not a member of a tightly regulated militia. Sarcasm aside, the only way to make sure people get encryption is to make it impossible to restrict the technology. That's how encryption ended up spreading. You don't put disruptive tech on every computer on the planet by waiting for permission.

“and on that day the ACLU and the EFF cited DC vs Heller (2010), and a crack appeared in the heavens and a loud voice spoke, saying ‘oi! wot’s all this then?!’”

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#147

Post by toast0 »

jolux wrote: post #143
toast0 wrote: post #75

Earlier quoted context omitted.

> This would require changing all the clients. Not really, the old clients would never send (or receive) end to end encrypted messages, so they don't need new UI to tell you that. That's the cost of unbounded backwards comptability. If you want to have 100% coverage of email users, changing all clients is part of the deal. But, uhhh, good luck with that. Server based standards are an easier lift --- you could build a…

>Of course it would be trivial for a hop in the delivery path to subvert that and remove the request, and all hops in delivery would still have message content access; but if people like it, a large majority of servers might support it in 5-10 years. You're describing TLS, and this is already happening.

Not just TLS, but a way to say, while composing a message, if it's can not be delivered via TLS with a valid certiticate, then don't deliver it. Which apparently already exists as REQUIRETLS https://www.rfc-editor.org/rfc/rfc8689.html

Published November 2019. I didn't see any data on support, and hadn't heard of it before looking just now.

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#148

Post by [deleted] »

quadrifoliate wrote: post #140
shp0ngle wrote: post #129

"How much do you trust the owner of this key to sign other keys properly? * I don't know * I do NOT trust * I trust marginally * I trust fully * I trust ultimately" This is a real pop-up I got the last time I tried to use PGP with Thunderbird. If people still get regular pop-ups like these, I don't think PGP will ever be popular. They might have switched to PEP (pretty easy privacy) that uses TOFU (trust-on-first-use…

I know it's virtually forbidden to discuss practical details of PGP on HN, but what do you think is the sticking point about that pop-up? It makes people think a little rather than trust blindly, which seems to be...good? I do agree that the marginally and fully options are useless. Wonder if adoption would be better if you just removed them, and were left with: - I don't know what PGP is (exit, opens documentation o…

[deleted]

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#149

Post by kevin_thibedeau »

deathgrips wrote: post #142
coderintherye wrote: post #135

Earlier quoted context omitted.

For those that don't click through, it repeats what is a fairly cogent argument. If cryptography is classified as a munition, then there should be legal room to argue we have the right to it as provided by the 2nd amendment.

Congrats, you don't get encrypted because you're not a member of a tightly regulated militia. Sarcasm aside, the only way to make sure people get encryption is to make it impossible to restrict the technology. That's how encryption ended up spreading. You don't put disruptive tech on every computer on the planet by waiting for permission.

There is no definition given for what "well regulated" entails. A bunch of nerds on the internet can certainly form their own militia to practice with crypto munitions.

Re: 21 years after the request OpenPGP support gets added to Thunderbird

#150

Post by TheDong »

thaumasiotes wrote: post #102
oconnore wrote: post #8

I do think there ought to be a way to do good cryptography in email. Email is not going away anytime soon, so giving up on it as a legitimate place where cryptography is needed seems too ivory tower for me. The “dead simple solution” is to just run the Signal protocol over SMTP, although I’m sure it’s possible there is a better design if you were to think about the specifics.

Isn't the "dead simple solution": 1. Write the message. 2. Encrypt the message. 3. Paste the encrypted message into the email client. Your odds of accidentally sending a message in the clear are zero.

And now to read and reply to it, someone has to copy it from the email client, decrypt it, edit their replies in inline, re-encrypt it, and paste it in.

As the number of people on the email chain approaches 2, the chance of someone accidentally copying+pasting the entire email chain decrypted into a reply reaches shockingly high levels.

A painful manual process where the simpler slightly-less painful path works, but results in insecurity happening, are not a good way to make sure security happens.

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