I’m not sure I completely agree here. For private use, this seems fine. However, this isn’t how email encryption is typically implemented in an enterprise environment. It’s usually handled at the mail gateway rather than on a per-user basis. Enterprises also ensure that the receiving side supports email encryption as well.
Your mail either needs to be encrypted reliably against real adversaries or it doesn't. A private emailing circle doesn't change that. If the idea here is, a private group of friends can just agree never to put anything in their subjects, or to accidentally send unencrypted replies, I'll just say I ran just such a private circle at Matasano, where we used encrypted mail to communicate about security assessment projects, and unencrypted replies happened.
> Your mail either needs to be encrypted reliably against real adversaries or it doesn't.
It is, GPG take care of that.
> If the idea here is, a private group of friends can just agree never to put anything in their subjects, or to accidentally send unencrypted replies
That’s not what I’m talking about. It’s an enterprise - you cannot send non-encrypted emails from your work mail account, the gateway takes care of it. It has many rules, including such based on the sender and recipient.
Surely, someone can print the mail and carry it out of the company’s premises, but at this point it’s intentional and the cat’s already out of the bag.
If you're relying on a trusted gateway, you don't need any of this; just do TLS to the gateway to exchange messages. This is how 95% of corporate "secure email" systems work.
But you don't know how many SMTP relays the recipient has and if they are all secured. E2E encryption, be it via GPG or x.509/SMIME, is still good in that case.
Can you give an example of an email provider or technology that’s doing GPG or SMIME at the gateway? I’ve never seen that configuration and it doesn’t seem like it would make sense.
Either it’s just theatre, encrypting emails internally and then stripping it when they’re delivered, or you still need every recipient to be managing their own keys anyways to be able to decrypt/validate what they’re reading.
I will not name it, but I worked on such product for some time. In fact it is still being sold, maybe 3rd decade already.
> you still need every recipient to be managing their own keys anyways to be able to decrypt/validate what they’re reading.
Nope, that is handled at the gateway on the receiving side.
edit: Again, the major point here is to ensure no plain text email gets relayed. TLS does not guarantee that plain text email doesn't get relayed by a wrongly configured relay on its route.
There's like one or two use cases where encrypting email could work. The best case I've come across--Bugzilla has the ability to let the user upload a public key to encrypt emails for updates to non-public bugs. It's not a big use case--pretty much the intersection of "must use email" and "can establish identity out of band," which does not describe most communication that uses email. (As tptacek notes in a sibling comment, you pretty much have to limit this to one-and-done stuff too, not anything that's going to be in an ongoing discussion, because leaks via unencrypted replies are basically guaranteed).
Even my doctor's office and local government agencies support PGP encrypted emails, and refuse to send personal data via unencrypted email, but tech nerds still claim no one can use it?
I'm yet to finish watching the talk, but it starts with them confirming the demo fraudulent .iso with sequoia also (they call it out by name), so this really makes me think. :)
Sequioa hasn't fixed the attack from the beginning of the talk, the one where they convert between cleartext and full signature formats and inject unsigned bytes into the output because of the confusion.
The latest version of a bad standard is still bad.
This page is a pretty direct indicator that GPG's foundation is fundamentally broken: you're not going to get to a good outcome trying to renovate the 2nd story.
There are people who use GPG for more than that. Those that are fine with just those two features, sure. Heck, you can encrypt with "openssh", no need for age. :D I have a bash function for encryption and decryption!
Why does Fedora / RPM still rely on GPG keys for verifying packages?
This is a staggering ecosystem failure. If GPG has been a known-lost cause for decades, then why haven't alternatives ^W replacements been produced for decades?
They are also correct, but that's indeed not what the person you replied to said.
> then why haven't alternatives ^W replacements been produced for decades?
Actually we do have alternatives for it.
For example Git supports S/MIME and could absolutely be used to sign commits and tags. Even just using self-signed certificates wouldn't be far off from what PGP offers. However if people used their digital IDs like many countries offer, mission-critical code could have signatures with verifiable strong identities.
Though there are other approaches as well, both for signing and for encrypting. It's more that people haven't really considered migrating.
But trust in Werner Koch is gone. Wontfix??