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There are many, many use-case problems with PGP and email, to the point that most serious security people just don't bother with PGP. It's relegated to niche an

There are many, many use-case problems with PGP and email, to the point that most serious security people just don't bother with PGP. It's relegated to niche and die-hard users. The problems are so many that it's better to use an alternative messaging platform that is built from the ground-up with encryption in mind, like Signal. For example... 1. what happens when you send an encrypted email, and the recipient forwards it? 2. What happens when the recipient replies? Will your original email be included encrypted, or decrypted? Most likely the latter, meaning the same cleartext is now present in two messages. 3. What happens when you email more than one person? What entity handles the encryption for each recipient? 3.a. what if only some of your recipients support encryption? What's the point of encrypting if you're sending some in the clear anyhow? 4. What happens when you email a mailing list, with unknown participants?... 5. What should be canonically encrypted? Just the message body? What about the subject, which is a header of the email? What about any other headers? 5.a. Oh you just want it signed? Again, what is canonically getting signed? How does that survive the many transformations the text receives in a conversation?

AceJohnny2 3y ago
I'd say the problem of PGP and email is that it suffers from a "90% of features is good enough" mindset that is prevalent in open-source (which otherwise isn't a bad thing!) But when it comes to true security, 90%, or even 99%, is so far from "good enough" as to be pointless.
- rovr138 3y ago
  Do you have examples? Not sure if you mean security or ergonomics.
colordrops 3y ago
These big companies could have extended or replaced the current mail protocol to support these cases if they wished.
- deleted 3y ago
  [deleted]
reaperman 3y ago
1) It's decrypted and forwarded re-encrypted with the receiver's public key. 2) It's decrypted and re-encrypted with your public key. 3) Same thing that happens right now? Two separate emails get sent out each encrypted separately with the receiver's public key. 3a) It gets sent unencrypted. Frontend client warns the sender. 4) Separate emails get sent out with the receivers' public keys. 5) Everything except the receiver's single email address. Optionally, everything except the receiver's and sender's email address for spam filtering. 5a) Everything. Not sure why any of this would prevent Apple, Gmail, and Office365 from implementing a transparent PGP encryption layer. If just those three entities worked this out, the vast, vast majority of emails in the western world would be encrypted effectively. Just because some emails wouldn't be well-encrypted doesn't change that this would be a huge benefit for privacy.
- withinboredom 3y ago
  All emails are basically signed these days via DKIM by your mail service. Each server along the chain should also be signing them too, so your whole path is known and validated. You can validate those keys via DNS. True story, I was an expert witness on a case once where I showed how the other guys were submitting forged emails into evidence -- by using DKIM signatures/hashes. That was probably some of the most fun I've ever had.
  - Infernal 3y ago
    I’ve always wondered about tampering of digital evidence like that, how much it might happen and not be detected, and what the penalty would be if it were.
    - withinboredom 3y ago
      Part of the work was explaining that a print out of an email is just a representation of the email, an actual email contains headers (like a digital stamp) that explain how the email got to where it is (in gmail -- "show original" -- that naming really helped, btw) and without it, you just have a piece of paper with words on it. The equivalent would be printing out the body of a newspaper article without the author or source. You have words, but you can't prove that it came from that newspaper unless someone else can corroborate it.
deleted 3y ago
[deleted]
autoexec 3y ago
> The problems are so many that it's better to use an alternative messaging platform that is built from the ground-up with encryption in mind, like Signal. I'm not sure signal is what people who really care about their security should be using. Signal refuses to update its privacy policy to reflect the fact that for years now they've been permanently storing sensitive user data in the cloud. At this point I consider the fact that the very first sentence of their privacy policy has been a lie since 2020 to be a dead canary. That, combined with their very unclear and misleading communications surrounding the data collection along with the dropping of highly popular features (the ability to handle unsecured SMS/MMS as well as secure communication) and inclusion of sketchy crypto features nobody asked for, makes me suspect even more that Signal may be telling people as loudly as they can to look for alternate solutions. To anyone unaware that Signal was collecting and forever storing sensitive personal data in the cloud, that should tell you everything you need to know about how trustworthy it is. For more info on this see: https://community.signalusers.org/t/proper-secure-value-security-pins-are-too-easy-to-brute-force-sgx-is-not-reliable-enough/15096 https://community.signalusers.org/t/proper-secure-value-secu... https://community.signalusers.org/t/dont-want-pin-dont-want-anything-stored-in-cloud/14057 https://community.signalusers.org/t/dont-want-pin-dont-want-... https://old.reddit.com/r/signal/comments/htmzrr/psa_disabling_pins_will_now_upload_nothing_to_the/fyjy7a5/ https://old.reddit.com/r/signal/comments/htmzrr/psa_disablin...
thayne 3y ago
> The problems are so many that it's better to use an alternative messaging platform that is built from the ground-up with encryption in mind, like Signal I mostly agree. Although I don't know of something that can really replace email. Signal for example is not great for long form content, is kind of difficult to use on a desktop, is tied to your phone number, doesn't have a way to programmatically send messages (besides unsanctioned third party clients), and doesn't have a good way to group messages into conversations or threads. Most other e2e encrypted system have similar limitations. Matrix is perhaps the most promising I've seen for replacing email. But the biggest problem is the network effect. It doesn't matter how good a system is if no one you know uses it.
LinuxBender 3y ago
It's relegated to niche and die-hard users. This is not entirely true. I am not allowed to mention their names but there are a myriad of companies that use PGP in their software integrations. It is very heavily used for B2B in the financial world. That isn't to say that devs don't shake their fists in anger when trying to do QA testing on software/library matrix of tools that businesses use with PGP, there is plenty of that. On a personal level I have taught many in my circle to use GPG with Thunderbird as it is really just a couple clicks to set it up and no effort to use it. Mozilla did a great job making that easy to use though I have no doubt that prior implementations had soured peoples experiences to the point of not wanting to try it again. Some of your examples are real issues though. Mailing lists are a pseudo-problem in that it doesn't really make sense to use on a public distribution. I've seen it used on Usenet in that fashion long ago but adoption was low for that use case and people complained they could not read the messages not intended for them and that they should use email directly to the people it was intended for instead. What happens when you email more than one person? What entity handles the encryption for each recipient? The email client handles this.

AceJohnny2 3y ago

I'd say the problem of PGP and email is that it suffers from a "90% of features is good enough" mindset that is prevalent in open-source (which otherwise isn't a bad thing!) But when it comes to true security, 90%, or even 99%, is so far from "good enough" as to be pointless.

rovr138 3y ago
Do you have examples? Not sure if you mean security or ergonomics.

colordrops 3y ago

These big companies could have extended or replaced the current mail protocol to support these cases if they wished.

deleted 3y ago
[deleted]

reaperman 3y ago

1) It's decrypted and forwarded re-encrypted with the receiver's public key. 2) It's decrypted and re-encrypted with your public key. 3) Same thing that happens right now? Two separate emails get sent out each encrypted separately with the receiver's public key. 3a) It gets sent unencrypted. Frontend client warns the sender. 4) Separate emails get sent out with the receivers' public keys. 5) Everything except the receiver's single email address. Optionally, everything except the receiver's and sender's email address for spam filtering. 5a) Everything. Not sure why any of this would prevent Apple, Gmail, and Office365 from implementing a transparent PGP encryption layer. If just those three entities worked this out, the vast, vast majority of emails in the western world would be encrypted effectively. Just because some emails wouldn't be well-encrypted doesn't change that this would be a huge benefit for privacy.

withinboredom 3y ago
All emails are basically signed these days via DKIM by your mail service. Each server along the chain should also be signing them too, so your whole path is known and validated. You can validate those keys via DNS. True story, I was an expert witness on a case once where I showed how the other guys were submitting forged emails into evidence -- by using DKIM signatures/hashes. That was probably some of the most fun I've ever had.
- Infernal 3y ago
  I’ve always wondered about tampering of digital evidence like that, how much it might happen and not be detected, and what the penalty would be if it were.
  - withinboredom 3y ago
    Part of the work was explaining that a print out of an email is just a representation of the email, an actual email contains headers (like a digital stamp) that explain how the email got to where it is (in gmail -- "show original" -- that naming really helped, btw) and without it, you just have a piece of paper with words on it. The equivalent would be printing out the body of a newspaper article without the author or source. You have words, but you can't prove that it came from that newspaper unless someone else can corroborate it.

deleted 3y ago

[deleted]

autoexec 3y ago

> The problems are so many that it's better to use an alternative messaging platform that is built from the ground-up with encryption in mind, like Signal. I'm not sure signal is what people who really care about their security should be using. Signal refuses to update its privacy policy to reflect the fact that for years now they've been permanently storing sensitive user data in the cloud. At this point I consider the fact that the very first sentence of their privacy policy has been a lie since 2020 to be a dead canary. That, combined with their very unclear and misleading communications surrounding the data collection along with the dropping of highly popular features (the ability to handle unsecured SMS/MMS as well as secure communication) and inclusion of sketchy crypto features nobody asked for, makes me suspect even more that Signal may be telling people as loudly as they can to look for alternate solutions. To anyone unaware that Signal was collecting and forever storing sensitive personal data in the cloud, that should tell you everything you need to know about how trustworthy it is. For more info on this see: https://community.signalusers.org/t/proper-secure-value-security-pins-are-too-easy-to-brute-force-sgx-is-not-reliable-enough/15096 https://community.signalusers.org/t/proper-secure-value-secu... https://community.signalusers.org/t/dont-want-pin-dont-want-anything-stored-in-cloud/14057 https://community.signalusers.org/t/dont-want-pin-dont-want-... https://old.reddit.com/r/signal/comments/htmzrr/psa_disabling_pins_will_now_upload_nothing_to_the/fyjy7a5/ https://old.reddit.com/r/signal/comments/htmzrr/psa_disablin...

thayne 3y ago

> The problems are so many that it's better to use an alternative messaging platform that is built from the ground-up with encryption in mind, like Signal I mostly agree. Although I don't know of something that can really replace email. Signal for example is not great for long form content, is kind of difficult to use on a desktop, is tied to your phone number, doesn't have a way to programmatically send messages (besides unsanctioned third party clients), and doesn't have a good way to group messages into conversations or threads. Most other e2e encrypted system have similar limitations. Matrix is perhaps the most promising I've seen for replacing email. But the biggest problem is the network effect. It doesn't matter how good a system is if no one you know uses it.

LinuxBender 3y ago

It's relegated to niche and die-hard users. This is not entirely true. I am not allowed to mention their names but there are a myriad of companies that use PGP in their software integrations. It is very heavily used for B2B in the financial world. That isn't to say that devs don't shake their fists in anger when trying to do QA testing on software/library matrix of tools that businesses use with PGP, there is plenty of that. On a personal level I have taught many in my circle to use GPG with Thunderbird as it is really just a couple clicks to set it up and no effort to use it. Mozilla did a great job making that easy to use though I have no doubt that prior implementations had soured peoples experiences to the point of not wanting to try it again. Some of your examples are real issues though. Mailing lists are a pseudo-problem in that it doesn't really make sense to use on a public distribution. I've seen it used on Usenet in that fashion long ago but adoption was low for that use case and people complained they could not read the messages not intended for them and that they should use email directly to the people it was intended for instead. What happens when you email more than one person? What entity handles the encryption for each recipient? The email client handles this.