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The author says not to use email encryption but what is the case for sending email in plain text? Is encrypted email detrimental to my privacy in some way that

The author says not to use email encryption but what is the case for sending email in plain text? Is encrypted email detrimental to my privacy in some way that unencrypted email is not? Or if the argument is that encrypted email is useless and no better than unencrypted email (since it is always unencrypted at rest) then what is the point of avoiding it in favor of the alternative? Aren't they equivalent, making the distinction meaningless? This is my problem with the article. It feels like it suffers from a bit of zero-sum fallacy. The statement here is, "it can be broken therefore it's fundamentally broken." I think it's more useful to think in terms of probabilities. If I disable password authentication for SSH and require public key authentication on my web server, an attacker can still get in by stealing my private key. That isn't a reason to take the opposite approach however - botnets commonly employ password-guessing attacks against entire IP ranges so you're not actually safer by avoiding this practice just because it isn't a perfect solution. There is no silver bullet for security, only endless layers of strategies and adaptations to edge cases. I did enjoy some of the points about the limitations of email encryption (the email chain example is a great reminder of how security is often more about human behavior than software). But I think the article could have been more compelling had it presented a less dogmatic thesis - perhaps "Email Encryption Won't Save You" or something like that.

ameliaquining 5y ago
The point being made is that, if something is sensitive enough that you would hesitate to send it in the clear, you should send it over Signal or some other system that doesn't have the security flaws that encrypted email has. Given that that option exists, and that encrypted email isn't suitable for many use cases that people are tempted to use it for (and is therefore an attractive nuisance securitywise), there's not much reason to use or support encrypted email at all.
- sneak 5y ago
  Normal people assume that email is a perfectly safe and secure way to transmit PII and other sensitive information, FWIW. The idea that "email is insecure" is not a widely known one.
  - viraptor 5y ago
    One of the best ways for the "secure online communication with normies" idea to die is to try to buy a house, especially when not living in a city close to the relevant banks/lawyers/etc. If you don't stop caring and send some document scan full of PII as an email attachment after a few weeks - congratulations.
    - tinus_hn 5y ago
      Does it matter? If you send it securely or provide the documents for scanning at the office, they will go on and email it around themselves anyway. If this ever is to stop there needs to be a strict ban on using email for these things combined with checks and serious consequences for violations. But that will not happen anywhere soon because guess what, the government that would have to create these rules violates them routinely.
    - sneak 5y ago
      You have to set up a corporation that has your attorney (or other trustworthy authorized representative) as manager of the LLC. Then all the docs have their name/email/signature, and the LLC can just keep the name of the member in its own records. It's still PII, but at least it isn't your PII. The droids that process these things are not going to change their means of communication or list of requirements for your deal, so you just have to ensure that the information being plugged into their systems is the information of a placeholder person (ie your attorney/business manager) instead of your own.
- mLuby 5y ago
  And when you send it over Signal you ALWAYS do so as a disappearing message, because as the article says, "every archived message will eventually leak." (Also you hope nobody quote-replies to your message.)
- gruez 5y ago
  What about the use case of "I don't want my email provider to be able to read all my past transactional emails at a moment's notice"? Sure, there are "reputable" non-encrypting mail providers, but why not have a reputable mail provider AND encryption, so there's a barrier if they try to go rogue?
- 08-15 5y ago
  Unfortunately, every device that has Signal installed, also has a root kit installed: the play store. If I use PGP-encrypted mail, I have to trust that the receiver is not stupid. If I use Signal, I have to trust that Google is not evil. Hmm...
  - growse 5y ago
    Play services / store isn't needed to run Signal (try it on AOSP, works just fine) and none of the iOS devices that run Signal have the play store installed.
Aerroon 5y ago
The case the article is trying to make is "don't use email". Use something else to send messages you wish to not be compromised.
- thayne 5y ago
  Unfortunately, there isn't a ubiquitous enough system for a lot of messages that should be secure. Like password reset links, financial and medical documents, vulnerability disclosures, etc. Besides the fact that no encrypted messaging system is sufficiently ubiquitous, Signal is not a great fit for these things because it is tied to a phone number (what would be the equivalent of security@mycompany.example? What if you don't want to give out your phone number, or your phone number changes?) And it is optimized for mobile messaging, and while there is a desktop app it isn't a great experience, and Signal strongly discourages third party clients. And I do love Signal, I just don't think it can really fully replace email. And I don't know of anything else that is well positioned to do so either, though I would love to learn of something.
  - OctopusLupid 5y ago
    I think Matrix would be a good fit. It strongly encourages E2EE and is federated like email.
yuvadam 5y ago
Encrypted email maybe works if both you and your counterparts are power users that know how to use GPG, or how to properly configure it through Thunderbird or any other email client. The moment you have to implement encrypted emails in a high-risk organization or ad-hoc collective, it all goes out the window. There are simply way too many pitfalls to get it working properly. You have to continuously educate your users and ensure they don't shoot themselves in the foot.
- PenguinCoder 5y ago
  What's the issue with S/MIME in such an organization?
jrm4 5y ago
This all day. I don't get why you'd take time out of your day to write "Stop Using Encrypted Email" instead of "Can Encrypted Email Be Done Right?" unless the answer is provable and obvious no.
- lamontcg 5y ago
  The author is arguing that it cannot ever be done right. Hasn't been fixed in 25 years and has fairly unfixable downgrade-to-plaintext attacks. You could enforce encrypted communications in the protocol by changing it, but you'd need to block downgrade-to-plaintext in the process, which would remove backwards compatibility and what you've got is something that looks like e-mail but is incompatible with the entire rest of the existing e-mail system and you've forked the whole ecosystem anyway. Might as well just write a better protocol and app while you're at it.
  - sneak 5y ago
    Unauthenticated TLS has trivial downgrade to plaintext attacks too, but it's still better than unencrypted HTTP because it upgrades the necessity for a passive attack into an active one.
    - tooltower 5y ago
      It is? I thought HSTS headers did a pretty good job of preventing downgrades, at least for sites I frequently visit.
    - tptacek 5y ago
      You've smuggled "unauthenticated" in there to make a reference to a mode of deployment that nobody thinks is secure. "Real" TLS (the alternative) doesn't have trivial downgrade attacks.
      - sneak 5y ago
        I mean --no-check-certificate. It's still better than http:. Eavesdropping requires an active attack instead of simply a passive one.
soneil 5y ago
The argument is essentially that the only thing worse than no security, is the illusion of security. Encryption on email is like a padlock on a suitcase. It makes you feel good, but really doesn't prevent much. It's common knowledge that you don't trust your valuables to unattended luggage. My reading of the article is that we should shed the illusion to help promote the same common knowledge for email.
deleted 5y ago
[deleted]
anm89 5y ago
This author seems to share an absolutist view of the sort Stallman likes to make. Your technology is imperfect and therefor should never be used

ameliaquining 5y ago

The point being made is that, if something is sensitive enough that you would hesitate to send it in the clear, you should send it over Signal or some other system that doesn't have the security flaws that encrypted email has. Given that that option exists, and that encrypted email isn't suitable for many use cases that people are tempted to use it for (and is therefore an attractive nuisance securitywise), there's not much reason to use or support encrypted email at all.

sneak 5y ago
Normal people assume that email is a perfectly safe and secure way to transmit PII and other sensitive information, FWIW. The idea that "email is insecure" is not a widely known one.
- viraptor 5y ago
  One of the best ways for the "secure online communication with normies" idea to die is to try to buy a house, especially when not living in a city close to the relevant banks/lawyers/etc. If you don't stop caring and send some document scan full of PII as an email attachment after a few weeks - congratulations.
  - tinus_hn 5y ago
    Does it matter? If you send it securely or provide the documents for scanning at the office, they will go on and email it around themselves anyway. If this ever is to stop there needs to be a strict ban on using email for these things combined with checks and serious consequences for violations. But that will not happen anywhere soon because guess what, the government that would have to create these rules violates them routinely.
  - sneak 5y ago
    You have to set up a corporation that has your attorney (or other trustworthy authorized representative) as manager of the LLC. Then all the docs have their name/email/signature, and the LLC can just keep the name of the member in its own records. It's still PII, but at least it isn't your PII. The droids that process these things are not going to change their means of communication or list of requirements for your deal, so you just have to ensure that the information being plugged into their systems is the information of a placeholder person (ie your attorney/business manager) instead of your own.
mLuby 5y ago
And when you send it over Signal you ALWAYS do so as a disappearing message, because as the article says, "every archived message will eventually leak." (Also you hope nobody quote-replies to your message.)
gruez 5y ago
What about the use case of "I don't want my email provider to be able to read all my past transactional emails at a moment's notice"? Sure, there are "reputable" non-encrypting mail providers, but why not have a reputable mail provider AND encryption, so there's a barrier if they try to go rogue?
08-15 5y ago
Unfortunately, every device that has Signal installed, also has a root kit installed: the play store. If I use PGP-encrypted mail, I have to trust that the receiver is not stupid. If I use Signal, I have to trust that Google is not evil. Hmm...
- growse 5y ago
  Play services / store isn't needed to run Signal (try it on AOSP, works just fine) and none of the iOS devices that run Signal have the play store installed.

Aerroon 5y ago

The case the article is trying to make is "don't use email". Use something else to send messages you wish to not be compromised.

thayne 5y ago
Unfortunately, there isn't a ubiquitous enough system for a lot of messages that should be secure. Like password reset links, financial and medical documents, vulnerability disclosures, etc. Besides the fact that no encrypted messaging system is sufficiently ubiquitous, Signal is not a great fit for these things because it is tied to a phone number (what would be the equivalent of security@mycompany.example? What if you don't want to give out your phone number, or your phone number changes?) And it is optimized for mobile messaging, and while there is a desktop app it isn't a great experience, and Signal strongly discourages third party clients. And I do love Signal, I just don't think it can really fully replace email. And I don't know of anything else that is well positioned to do so either, though I would love to learn of something.
- OctopusLupid 5y ago
  I think Matrix would be a good fit. It strongly encourages E2EE and is federated like email.

yuvadam 5y ago

Encrypted email maybe works if both you and your counterparts are power users that know how to use GPG, or how to properly configure it through Thunderbird or any other email client. The moment you have to implement encrypted emails in a high-risk organization or ad-hoc collective, it all goes out the window. There are simply way too many pitfalls to get it working properly. You have to continuously educate your users and ensure they don't shoot themselves in the foot.

PenguinCoder 5y ago
What's the issue with S/MIME in such an organization?

jrm4 5y ago

This all day. I don't get why you'd take time out of your day to write "Stop Using Encrypted Email" instead of "Can Encrypted Email Be Done Right?" unless the answer is provable and obvious no.

lamontcg 5y ago
The author is arguing that it cannot ever be done right. Hasn't been fixed in 25 years and has fairly unfixable downgrade-to-plaintext attacks. You could enforce encrypted communications in the protocol by changing it, but you'd need to block downgrade-to-plaintext in the process, which would remove backwards compatibility and what you've got is something that looks like e-mail but is incompatible with the entire rest of the existing e-mail system and you've forked the whole ecosystem anyway. Might as well just write a better protocol and app while you're at it.
- sneak 5y ago
  Unauthenticated TLS has trivial downgrade to plaintext attacks too, but it's still better than unencrypted HTTP because it upgrades the necessity for a passive attack into an active one.
  - tooltower 5y ago
    It is? I thought HSTS headers did a pretty good job of preventing downgrades, at least for sites I frequently visit.
  - tptacek 5y ago
    You've smuggled "unauthenticated" in there to make a reference to a mode of deployment that nobody thinks is secure. "Real" TLS (the alternative) doesn't have trivial downgrade attacks.
    - sneak 5y ago
      I mean --no-check-certificate. It's still better than http:. Eavesdropping requires an active attack instead of simply a passive one.

soneil 5y ago

The argument is essentially that the only thing worse than no security, is the illusion of security. Encryption on email is like a padlock on a suitcase. It makes you feel good, but really doesn't prevent much. It's common knowledge that you don't trust your valuables to unattended luggage. My reading of the article is that we should shed the illusion to help promote the same common knowledge for email.

deleted 5y ago

[deleted]

anm89 5y ago

This author seems to share an absolutist view of the sort Stallman likes to make. Your technology is imperfect and therefor should never be used