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Comment by dylan604 | Hacker News Reader

The biggest issue of using PGP was using PGP. You were pretty nerdy to be on the internet back then, but even then using PGP was beyond what the majority of people wanted to do. Exchanging keys was problematic. Writing text in one app, encrypting in another app, copying encrypted back to an email was just tiresome.

I'm still glad that it existed as its mere existence seems to have pushed things in the right direction as far as protecting everyone's ability to use encryption if they chose. It just never became the panacea it was envisioned to be.

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One big usability issue these days is that PGP identities come in the form of a file. Lots of people don't have the concept of that anymore.

Dunno that things have gotten much better over the years. End to end encryption is still fairly unusable to most. I think that rather than spending so much time on the cryptography we should instead work on a E2EE usability standard. Having everyone doing their own thing with respect to usability is not working out.

ASCII armored exports suitable for plain text copying and pasting and inclusion in other documents and messages seem to be the norm for sharing. Keys are referred to by keyid or email. To the key database, files seem more like an implementation detail.

It provides the tools necessary to implement a simpler workflow.

The term E2EE has been subverted. Apps like WhatsApp claiming to be E2EE, but only if you actually enable it, so that people think they are being encrypted when they are not does not help. ProtonMail falls into this as well where allowing email to non-encrypted addresses means there is no encryption. It's obvious to some, but not so for the majority. Very few people read the caveats that WhatsApp and ProtonMail provide.

Telegram is the worst though, everyone thinks it's secure and it actually has no security features at all

Can you explain WhatsApp further? Every 1:1 chat I have typically leaves a little note saying it's e2ee

WhatsApp doesn't have any option to enable/disable encryption for standard messages that I can see. Business chat messages are not encrypted and neither are backups (by default) but if Alice messages Bob on a fresh WhatsApp install, the message is E2EE (as far as I know). Is that incorrect?

WhatsApp backups are not encrypted by default.

That’s Telegram. WhatsApp doesn’t have a toggle except for backups.

> ProtonMail falls into this as well where allowing email to non-encrypted addresses means there is no encryption.

You can send password protected mails that the recipient can read in the browser given a pre-shared password. https://proton.me/support/password-protected-emails

> One big usability issue these days is that PGP identities come in the form of a file. Lots of people don't have the concept of that anymore.

Mind. Blown.

There were (are? it's been a while) many PGP users on the various darkweb markets. It was great fun teaching people to use it and actually having a community to use it with.

It was pretty awkward to later emerge as the PGP expert at work. I was at that time a bit shy about explaining how I got so comfortable with it.

The fundamental idea of technology such as PGP is that the percentage of stuff worth finding for the authorities needs to be really low. Ie. an incredible amount of "legitimate" innocent traffic needs to be flowing through the technology.

Otherwise, anyone who is using it at all will get court ordered and then, with our current system, you just lose.

Tor solves this by making traffic entirely homogenous such that any "it could be anyone" and by making nodes extraordinarily easy to host (such that any nerd can just leave one running 24/7). Even so there are way too few nodes.

But PGP-over-email is way too metadata leaky, and if you're doing anything that actually has a threat model, you need PGP-over-email to be itself common.

Even today, you still need an external program to your email app to enable encrypted messages with in the email app. With that, the number of encrypted emails will be extremely low relatively. Even looking at Tor, the amount of users is still much lower than the internet in general. To the point, I doubt a very high amount of traffic is "regular" traffic to raise the noise floor.

Huh, Thunderbird ships with a PGP implementation by default? And it's actually very easy to use.

And how many people use Thunderbird compared to any of the other email clients? People keep pulling out esoteric products as an example of how PGP is not hard to use.

It's easy to explain. "I use PGP for my personal notes (symmetric) and for e-mailing my security conscious friends (public-key)". That's sufficient and not awkward.

Yes but that explanation doesn't help you teach people how to use it in an adversarial context. Then they're just following arbitrary rules set down by privacy nerds for seemingly arbitrary reasons.

To be honest: I keep hearing that PGP was / is difficult to use. That couldn‘t be further from the truth - but somehow it has become an urban myth. From the very first versions that I used on my first Mac up to GPG Mail or Proton Mail I never encountered any significant difficulties and could successfully exchange messages with my peers - both in business and private contexts.

I once had a chat with a security professor who had decided to try to get his group to use encrypted email for all of their communications. And they just couldn't get mailing lists working right with encrypted email.

The sender has to encrypt with everyones individual key wonder why he couldn't get it to work.

In general, a session/thread ephemeral key pair is exchanged with the participants, and only each users private origin signing validates each sender sections. Since the signatures are passively checked, it does not need redone after each append operation.

Thus, participants are pooled under 1 time constrained key exchange, participants sections origins are signed/time-stamped, and the ciphertext expires on a schedule.

Why? so at some future time side-channel key exfiltration can't be used to data mine the entire history of past tapped conversations/ciphertext. Even if a private signing key is stolen, it is difficult to rebuild the lost ephemeral key session.

Have a nice day. =3

My eyes glazed over reading that. I feel like 30 years of internet has proven one thing: the simplest solution always wins. PGP is many things, but simple and obvious are not among them.

Mozilla Thunderbird e-mail client, and Android k9 mail makes pgp/gpg public key handling fairly trivial.

Depends what you do, and if your organization has a persistent clown infestation. Some big business folks still use email as a human to API interface.

Running out-of-band public keychains is not something most people will ever need. =3

Please, enlighten me on how you used PGP where calling it hard to use is so far from the truth. ProtonMail only works if you send messages to another ProtonMail user. It does not protect you when you email someone else.

> ProtonMail only works if you send messages to another ProtonMail user.

Your wording is not entirely accurate.

ProtonMail works perfectly well with external PGP. You can import third-party keys and IIRC it also supports WKD.

So its not "only another ProtonMail user".

IN ADDITION .... you can also send an encrypted, password protected message to a non-Proton Mail email address. The recipient can read it in the browser: https://proton.me/support/password-protected-emails

Your use of ProtonMail+PGP is not how people expect ProtonMail to work when it is claimed to be encrypted email. ProtonMail+PGP is no different than GMail+PGP or AOL+PGP or FastMail+PGP or $coolNameMail+PGP. So what's your point?

Anything+PGP can be encrypted. You still have to use PGP which means creating public/private key pairs, store them correctly, and understand when to use the public key and when to use the private key. You still then need to know how to exchange keys in a trustworthy manner, but that's after you convince someone else to do all of that on their end as well.

So yeah, it's dead simple <facepalm>

What GP likely means is that a Protonmail user can exchange encrypted emails with a non-Protonmail user without doing anything except importing the non-Protonmail user's keys once.

This could allow a single technical user with an elaborate PGP key and email setup to convince his or her social circle (or at least email circle) to switch to Protonmail and follow a set of (comparatively) simple steps to get Proton to recognize the key to their non-Proton address.

Thereby having PGP-encrypted conversations with users who don't know how PGP works, but followed their friends' instructions to use a slightly different webmail interface. Meanwhile the technical user can use a smartcard, a self-hosted email server, or other madness that a normal user would never tolerate.

Thank you KAMSPioneer. This is exactly what I meant.

There is AFAIK only one other email service that offers a similar level of functionality, and that is Mailbox.org.

However the proton UI/UX experience for importing and managing keys is much better for the non-technical user in Proton. The UI/UX in Mailbox.org is messy.

"GMail+PGP or AOL+PGP or FastMail+PGP or $coolNameMail+PGP" is not the same thing and I hope the GP who replied to me knows that full well. ;)

At least the versions I remember had a really bad UX for marking keys as trusted.

The correct operation for (even locally) marking "this key belongs to person X" is signing the key. Marking it as "trusted" indicates "this key is a CA that can create statements who other keys belong to", but it's easier to find/"understand".

So if you haven't first studied the details of the security model and terminology, you just start increasing the trust level on the key of your communication partner until the warnings go away, not realizing that by doing this, you've made that key a CA and the reason the warnings disappeared is because you now trust the self-signature (in addition to all other signatures the key issued).

It's still extremely difficult.

If we assume that the threshold of what is "difficult" is for example 1) installing a desktop application, or even running a deskop OS.

2) Running an email provider other than what you are already doing (gmail, hotmail, yahoo mail, ...), or switching email providers

3) Copying and pasting text or using files.

This was perhaps a viable thing to do for users in 2005 because if you were on the internet, chances are you at least had a desktop computer, and if you used email chances are you already had to struggle with an email client.

But now? Anything that isn't as easy as installing an app on your device (a device that isn't a full computer) is "difficult".

It's not that it's harder today, it's that everything else is easier (Like telegram/signal and other privacy-minded services), and that there are now 6 billion internet users and most never used a computer and never will.

> It's still extremely difficult.

I don't see how. You just type "gpg -e -r receipient@domain.com filename.txt". It doesn't get much simpler than that. It's not like you are using ffmpeg, imagemagick, or other programs with a hundred switches in it.

Also PGP/GnuPG is not only for email. I encrypt and decrypt hundreds and hundreds of payloads per day, programmatically between trusted and untrusted networks.

And it is mandatory for each employee to upload their public key to our keystore so that we can deliver private information to them securely over Slack, Teams, or other communication channels.

> You just type "gpg -e -r receipient@domain.com filename.txt".

I assure you it is not that simple. For example, I'm a HN user, developer since 30 years. I know that you referred to what's known as a "terminal" or "shell" here, but that's already way WAY too difficult for 99.9% of users.

And even in my terminal I can assure you it won't work: "'gpg' is not recognized as an internal or external command, operable program or batch file."

I could install it. It would be a right pain though. and it doesn't help if the recipient of my email can't install it without me sending a long list of instructions!

Meanwhile my dad had zero problems installing signal. There's a difference to how easy it gets.

Tell me you're a nerd without telling me you're a nerd. Maybe you've moved the goalposts to "it's easy for tech dorks" vs "it's a total pain in the arse for your mom to use'. If the goal is to have encrypted email everywhere, running anything in via command line is out. If you can't recognize that, then you're clearly just trolling

I used it for a little while and Turnpike email software from the UKs Demon Internet integrated it pretty well.

The problem was only one other person I knew actually used it, it didn't really have a justifiable use for most people.

I did use the encrypted mountable drives for a while, that worked very well. I since moved to TrueCrypt and now onto Vercrypt and haven't used a PGP product for probably over 15 years.

Shame really but it just didn't get enough traction.

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