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For me, everything has been said here already: https://latacora.micro.blog/2020/02/19/stop-using-encrypted.html https://latacora.micro.blog/2020/02/19/stop-usin

For me, everything has been said here already: https://latacora.micro.blog/2020/02/19/stop-using-encrypted.html https://latacora.micro.blog/2020/02/19/stop-using-encrypted.... > Ordinary people don’t exchange email messages that any powerful adversary would bother to read, and for those people, encrypted email is LARP security. It doesn’t matter whether or not these emails are safe, which is why they’re encrypted so shoddily. Totally agree that there is no way of doing email right. If you want security, use other messaging systems, like signal, for all the reasons explained in that post.

thepangolino 5y ago
ekianjo 5y ago
> If you want security, use other messaging systems, like signal, signal is not decentralized and requires phone numbers tied to your real identity. no thanks.
- Demcox 5y ago
  Try Session [0]. Decentralized, no phone numbers and adding contacts is done by either sharing your ID or an QR-code. It works well but, at this time, only texting. Does have pretty apps for iOS/Android and most desktops OS's [0]https://getsession.org/ https://getsession.org/ EDIT grammar
  - Rayhem 5y ago
    Has session had a proper security audit anywhere?
  - chaxor 5y ago
    Session is fantastic - definitely the best messaging system I have seen so far. Signal in second place due to the phone number tracking and non decentralized status stated above.
b112 5y ago
There are plenty of ways of doing email right, but we've lost what we had in the early days, the ability to form concensus, and enact change, via RFCs. Mostly because the big boys want control.
- phh 5y ago
  > Mostly because the big boys want control. I'd rather say the issue is that the big boys' business is NOT mails, so their goal is to provide the minimum viable mail service, and not spend one dollar more on it. While once upon a time, when companies were actually providing email service, they had to innovate to keep on top.
  - b112 5y ago
    Mail providers never wrote rfcs. Nor are they expensive, just concensus requiring. If email was encrypted at rest, gmail would disappear overnight. Gmail's whole purpose is end user data gathering, for profit. Many other mail providers are the same.
  - posterboy 5y ago
    > I'd rather say the issue is that the big boys' business is NOT mails, so their goal is to provide the minimum viable mail service, and not spend one dollar more on it. Plenty of money was spent criminalising crypto by the big boys. Even disregarding that fact, your equation makes no sense because AOL or whatever big BS you have in mind has null interest providing a product they have to spend money on with zero realistic ROI. Since arpa net arose eventually from the same party poopers, nothing of this should come as a real surprise.
yosamino 5y ago
There is a very good point about the difficult-to-impossibility of securing email. BUT: > Ordinary people don’t exchange email messages that any powerful adversary would bother to read, This just one hundred percent incorrect and it completely misstates the problem. The problem is not that Alice and Bob are the focus of intensely focused surveillance, in the sense that they are up against a powerful adversary themselves. The problem is that Alice and Bob live in a society where those who can and want to make such decisions, are implementing drag-net surveillance at every possible corner of society that they can get away with. There is a powerful adversary and it would very much like to to read any and all of our communication. In almost all cases this is consequence-free for Alice and Bob - but this is not Freedom. My communication is mine it's not there for google so scan for ways to sell me useless shit, and it's not there for Big Brother for training their precog-ML models on it. The threat model is not "The CIA wants to rubberhose me into revealing information" it's "The NSA routinely opens all of my letters, just to make sure I am not a terrorist/commie/vagrant/etc".
michaelt 5y ago
> It doesn’t matter whether or not these emails are safe, which is why they’re encrypted so shoddily. Right now my bank, pension fund, utility supplier etc regularly e-mail me to inform me that a new statement is available. But they don't attach the statement to the e-mail... because "it isn't secure" So there is real-world demand for a properly secured e-mail system. If we could jump in a time machine, go back 50 years and add end-to-end encryption to e-mail, I'd be getting my bank statements by e-mail. (The chance of my bank deciding to deploy PGP is approximately one in a billion - which is why we'd need a time machine)
- moviuro 5y ago
  Does your bank at least use STARTTLS? I know banks that don't. https://try.popho.be/email.html#tests https://try.popho.be/email.html#tests
- danShumway 5y ago
  > So there is real-world demand for a properly secured e-mail system. There is real-world demand for a properly secured messaging system (either real-time or asynchronous) that is as ubiquitous, as accessible, and as technologically neutral/decentralized as email. I think you hit the nail on the head that if we could go back in time and email was encrypted from the start, it would be great, and there is a demand for that. But people keep trying to do that time travel by adding encryption after the fact, and like you I just don't think PGP works for that, I think it's throwing duck tape on top of a technology that is just not designed to handle it. I'm not saying we should drop all email and move to something like Matrix, I still use email today for a lot of stuff. And I'm definitely not saying everyone should use Signal as a full email replacement (the phone number requirement and centralization problems make it unsuitable). But in the long, long term it would very likely be easier to drop email and move everyone everywhere to Matrix (or something else, it doesn't have to be an instant messenger), than it would be to try and retroactively make email encryption work well.
  - andi999 5y ago
    What seems to be the problem with pgp (apart from nobody using it)
xfer 5y ago
I can also screenshot my device showing signal/whatsapp, that doesn't make them insecure. There is a lot of email based verification/authentication happening which would benefit if the email encryption was more widely accepted.
upofadown 5y ago
"Stop Using Encrypted Email" is mostly a weak restatement of "The PGP Problem". That anti-PGP rant has issues[1] that are relevant here. The new bit is the idea that someone will leak an email with an unencrypted CC: or forward. That's an easy to resolve user factors issue. If we were actually encrypting our emails then attempts to send unencrypted emails could easily be highlighted and discouraged. Long form asynchronous messaging is important and useful, particularly in business. You can't just wave it away. By nature it can be made much more secure than something like an instant messenger[2]. The Cellebrite attack against Signal is a good example of that. Cellebrite gets all the archived messages in the case of Signal and none of the PGP messages. [1] https://articles.59.ca/doku.php?id=pgpfan:tpp https://articles.59.ca/doku.php?id=pgpfan:tpp [2] https://articles.59.ca/doku.php?id=em:emailvsim https://articles.59.ca/doku.php?id=em:emailvsim
- tptacek 5y ago
  Long-form asynchronous messaging is important and useful. It's just that SMTP email makes it virtually impossible to do so securely. As the author of both documents you cited, I take issue with the idea that one is a restatement of the other; that's obviously not true. The concerns in "S.U.E.A." are endemic to all forms of encrypted SMTP email, and the concerns in "T.P.P." are endemic to most possible uses of PGP. They're related sets of problems, but not even close to perfectly intersecting sets; the MasterCard logo, not the Toyota logo as you'd have it.
IncRnd 5y ago
Except there are many other emails people don't want to be read by the wrong party. A powerful adversary or nation-state is not the only adversary.
harryvederci 5y ago
> Ordinary people don’t exchange email messages that any powerful adversary would bother to read Do you have glasses? - Could've gotten you killed under a different regime in a different time. Do you own foreign books? - Could've gotten you killed under a different regime in a different time. Do you have a mental disorder? - Could've gotten you killed under a different regime in a different time. Is your religion not the majority in your country? - ... Now consider the fact that regimes change. How uninteresting are your emails?
- posterboy 5y ago
  > Do you have glasses? - Could've gotten you killed under a different regime in a different time. Really, where then? Suppose today it's opposite: Eye Sight will detoriate when not wearing proscription glasses, which gives actual minus points on sight and maybe three pedestrian red lights worth in negative social credit.
  - rsync 5y ago
    During the Cambodia genocide[1]: "... people who were stereotypically thought of as having intellectual qualities, such as wearing glasses or speaking multiple languages, were executed out of fear that they would rebel against the Khmer Rouge." [1] https://en.wikipedia.org/wiki/Cambodian_genocide https://en.wikipedia.org/wiki/Cambodian_genocide
- fguerraz 5y ago
  And that is exactly the point made in that article. If what you put in that email can get you killed, then don't put it in an email, even encrypted. There are just too many ways things can go wrong, and of course they will go wrong at some point. If you need confidentiality you need, at the minimum, disappearing messages, and for that to be the case all the way, you can't rely on decentralisation systems with various implementations. Sorry for interoperable decentralised lovers, that includes myself, but you need control over the whole chain. And email is just the opposite of this.
godelski 5y ago
>> Ordinary people don’t exchange email messages that any powerful adversary would bother to read Wait, what? Adversaries do read emails of ordinary/average people. From Google[0] to the NSA[1]. Are we just pretending this doesn't happen? [0] https://web.archive.org/web/20190331015638/https://www.wsj.com/articles/techs-dirty-secret-the-app-developers-sifting-through-your-gmail-1530544442 https://web.archive.org/web/20190331015638/https://www.wsj.c... [1] https://www.theverge.com/2017/4/28/15474828/nsa-surveillance-snowden-collection-email-702 https://www.theverge.com/2017/4/28/15474828/nsa-surveillance...
OrvalWintermute 5y ago
The problem with that link is pretty clear: (1) SMIME/x509, and national security variants are incredibly popular for intra-organizational secure email (2) Secure Webmails have came on the scene in a big way. Where SMIME/x509 fails, web-of-trust based solutions succeeds, and vice versa. Working across both areas means we need solutions to bridge between the two worlds, and to buttress each other respective weaknesses in the trust model.

thepangolino 5y ago

ekianjo 5y ago

> If you want security, use other messaging systems, like signal, signal is not decentralized and requires phone numbers tied to your real identity. no thanks.

Demcox 5y ago
Try Session [0]. Decentralized, no phone numbers and adding contacts is done by either sharing your ID or an QR-code. It works well but, at this time, only texting. Does have pretty apps for iOS/Android and most desktops OS's [0]https://getsession.org/ https://getsession.org/ EDIT grammar
- Rayhem 5y ago
  Has session had a proper security audit anywhere?
- chaxor 5y ago
  Session is fantastic - definitely the best messaging system I have seen so far. Signal in second place due to the phone number tracking and non decentralized status stated above.

b112 5y ago

There are plenty of ways of doing email right, but we've lost what we had in the early days, the ability to form concensus, and enact change, via RFCs. Mostly because the big boys want control.

phh 5y ago
> Mostly because the big boys want control. I'd rather say the issue is that the big boys' business is NOT mails, so their goal is to provide the minimum viable mail service, and not spend one dollar more on it. While once upon a time, when companies were actually providing email service, they had to innovate to keep on top.
- b112 5y ago
  Mail providers never wrote rfcs. Nor are they expensive, just concensus requiring. If email was encrypted at rest, gmail would disappear overnight. Gmail's whole purpose is end user data gathering, for profit. Many other mail providers are the same.
- posterboy 5y ago
  > I'd rather say the issue is that the big boys' business is NOT mails, so their goal is to provide the minimum viable mail service, and not spend one dollar more on it. Plenty of money was spent criminalising crypto by the big boys. Even disregarding that fact, your equation makes no sense because AOL or whatever big BS you have in mind has null interest providing a product they have to spend money on with zero realistic ROI. Since arpa net arose eventually from the same party poopers, nothing of this should come as a real surprise.

yosamino 5y ago

There is a very good point about the difficult-to-impossibility of securing email. BUT: > Ordinary people don’t exchange email messages that any powerful adversary would bother to read, This just one hundred percent incorrect and it completely misstates the problem. The problem is not that Alice and Bob are the focus of intensely focused surveillance, in the sense that they are up against a powerful adversary themselves. The problem is that Alice and Bob live in a society where those who can and want to make such decisions, are implementing drag-net surveillance at every possible corner of society that they can get away with. There is a powerful adversary and it would very much like to to read any and all of our communication. In almost all cases this is consequence-free for Alice and Bob - but this is not Freedom. My communication is mine it's not there for google so scan for ways to sell me useless shit, and it's not there for Big Brother for training their precog-ML models on it. The threat model is not "The CIA wants to rubberhose me into revealing information" it's "The NSA routinely opens all of my letters, just to make sure I am not a terrorist/commie/vagrant/etc".

michaelt 5y ago

> It doesn’t matter whether or not these emails are safe, which is why they’re encrypted so shoddily. Right now my bank, pension fund, utility supplier etc regularly e-mail me to inform me that a new statement is available. But they don't attach the statement to the e-mail... because "it isn't secure" So there is real-world demand for a properly secured e-mail system. If we could jump in a time machine, go back 50 years and add end-to-end encryption to e-mail, I'd be getting my bank statements by e-mail. (The chance of my bank deciding to deploy PGP is approximately one in a billion - which is why we'd need a time machine)

moviuro 5y ago
Does your bank at least use STARTTLS? I know banks that don't. https://try.popho.be/email.html#tests https://try.popho.be/email.html#tests
danShumway 5y ago
> So there is real-world demand for a properly secured e-mail system. There is real-world demand for a properly secured messaging system (either real-time or asynchronous) that is as ubiquitous, as accessible, and as technologically neutral/decentralized as email. I think you hit the nail on the head that if we could go back in time and email was encrypted from the start, it would be great, and there is a demand for that. But people keep trying to do that time travel by adding encryption after the fact, and like you I just don't think PGP works for that, I think it's throwing duck tape on top of a technology that is just not designed to handle it. I'm not saying we should drop all email and move to something like Matrix, I still use email today for a lot of stuff. And I'm definitely not saying everyone should use Signal as a full email replacement (the phone number requirement and centralization problems make it unsuitable). But in the long, long term it would very likely be easier to drop email and move everyone everywhere to Matrix (or something else, it doesn't have to be an instant messenger), than it would be to try and retroactively make email encryption work well.
- andi999 5y ago
  What seems to be the problem with pgp (apart from nobody using it)

xfer 5y ago

I can also screenshot my device showing signal/whatsapp, that doesn't make them insecure. There is a lot of email based verification/authentication happening which would benefit if the email encryption was more widely accepted.

upofadown 5y ago

"Stop Using Encrypted Email" is mostly a weak restatement of "The PGP Problem". That anti-PGP rant has issues[1] that are relevant here. The new bit is the idea that someone will leak an email with an unencrypted CC: or forward. That's an easy to resolve user factors issue. If we were actually encrypting our emails then attempts to send unencrypted emails could easily be highlighted and discouraged. Long form asynchronous messaging is important and useful, particularly in business. You can't just wave it away. By nature it can be made much more secure than something like an instant messenger[2]. The Cellebrite attack against Signal is a good example of that. Cellebrite gets all the archived messages in the case of Signal and none of the PGP messages. [1] https://articles.59.ca/doku.php?id=pgpfan:tpp https://articles.59.ca/doku.php?id=pgpfan:tpp [2] https://articles.59.ca/doku.php?id=em:emailvsim https://articles.59.ca/doku.php?id=em:emailvsim

tptacek 5y ago
Long-form asynchronous messaging is important and useful. It's just that SMTP email makes it virtually impossible to do so securely. As the author of both documents you cited, I take issue with the idea that one is a restatement of the other; that's obviously not true. The concerns in "S.U.E.A." are endemic to all forms of encrypted SMTP email, and the concerns in "T.P.P." are endemic to most possible uses of PGP. They're related sets of problems, but not even close to perfectly intersecting sets; the MasterCard logo, not the Toyota logo as you'd have it.

IncRnd 5y ago

Except there are many other emails people don't want to be read by the wrong party. A powerful adversary or nation-state is not the only adversary.

harryvederci 5y ago

> Ordinary people don’t exchange email messages that any powerful adversary would bother to read Do you have glasses? - Could've gotten you killed under a different regime in a different time. Do you own foreign books? - Could've gotten you killed under a different regime in a different time. Do you have a mental disorder? - Could've gotten you killed under a different regime in a different time. Is your religion not the majority in your country? - ... Now consider the fact that regimes change. How uninteresting are your emails?

posterboy 5y ago
> Do you have glasses? - Could've gotten you killed under a different regime in a different time. Really, where then? Suppose today it's opposite: Eye Sight will detoriate when not wearing proscription glasses, which gives actual minus points on sight and maybe three pedestrian red lights worth in negative social credit.
- rsync 5y ago
  During the Cambodia genocide[1]: "... people who were stereotypically thought of as having intellectual qualities, such as wearing glasses or speaking multiple languages, were executed out of fear that they would rebel against the Khmer Rouge." [1] https://en.wikipedia.org/wiki/Cambodian_genocide https://en.wikipedia.org/wiki/Cambodian_genocide
fguerraz 5y ago
And that is exactly the point made in that article. If what you put in that email can get you killed, then don't put it in an email, even encrypted. There are just too many ways things can go wrong, and of course they will go wrong at some point. If you need confidentiality you need, at the minimum, disappearing messages, and for that to be the case all the way, you can't rely on decentralisation systems with various implementations. Sorry for interoperable decentralised lovers, that includes myself, but you need control over the whole chain. And email is just the opposite of this.

godelski 5y ago

>> Ordinary people don’t exchange email messages that any powerful adversary would bother to read Wait, what? Adversaries do read emails of ordinary/average people. From Google[0] to the NSA[1]. Are we just pretending this doesn't happen? [0] https://web.archive.org/web/20190331015638/https://www.wsj.com/articles/techs-dirty-secret-the-app-developers-sifting-through-your-gmail-1530544442 https://web.archive.org/web/20190331015638/https://www.wsj.c... [1] https://www.theverge.com/2017/4/28/15474828/nsa-surveillance-snowden-collection-email-702 https://www.theverge.com/2017/4/28/15474828/nsa-surveillance...

OrvalWintermute 5y ago

The problem with that link is pretty clear: (1) SMIME/x509, and national security variants are incredibly popular for intra-organizational secure email (2) Secure Webmails have came on the scene in a big way. Where SMIME/x509 fails, web-of-trust based solutions succeeds, and vice versa. Working across both areas means we need solutions to bridge between the two worlds, and to buttress each other respective weaknesses in the trust model.