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I'm giving up on PGP

blog.filippo.io

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Re: I'm giving up on PGP

#311

Post by dom0 »

devilsavocado wrote: post #107

People who use PGP keys, can you give examples of your use? I'm genuinely curious. Who are you contacting, or who is contacting you? The author says he only receives 2 encrypted emails a year. Not only do I not have a PGP key, I don't think I've ever found myself in a situation where it was even an option to use one.

    1) Company communication
    2) Signing critical commits, tags
    3) Encrypted-mail-to-self
    4) Encrypting critical files
    5) Communicating about security vulnerabilities
I don't use it for backups (I use Borg), or for SSH (25519 keys).

Re: I'm giving up on PGP

#312

Post by blunte »

The #1 problem, beyond the usability issues, is that most users still just do not care. They are willfully ignorant (a mentality which is actively celebrated these days in some influential countries), and cannot be convinced in the value of privacy or security.

I have tried without much success to get people to move to ProtonMail. I have tried without much success to get people to move to Wire messenger. (And incidentally, the author mentions Signal and WhatsApp... I wonder why he doesn't use Wire?)

So without consumers who care, the only audience for PGP and other security focused tools are the geeks who too easily tolerate bad interfaces.

Re: I'm giving up on PGP

#313

Post by mbrock »

cowholio4 wrote: post #248
devilsavocado wrote: post #107

People who use PGP keys, can you give examples of your use? I'm genuinely curious. Who are you contacting, or who is contacting you? The author says he only receives 2 encrypted emails a year. Not only do I not have a PGP key, I don't think I've ever found myself in a situation where it was even an option to use one.

- All internal company emails. - Mailing Lists Side note: using pgp with MacOs Mail is super easy https://gpgtools.org/ (the project is currently working on Sierra support)

Super easy until you upgrade your operating system and suddenly you can't use your mail client for months while the understaffed open source project is trying to reverse engineer whatever Apple changed...

Re: I'm giving up on PGP

#314

Post by vic-traill »

at612 wrote: post #228
user5994461 wrote: post #209

Earlier quoted context omitted.

I have to partially disagree with that. Calling PGP an utter failure is an understatement. Just like calling a cat a small tiger. PGP is possibly the WORST experience in usability for any well known software that ever lived. This thing should be taught in courses for decades to come as how to fail a product by 1) having no UI 2) no integrations with anything 3) zero usability 4) not even trying to give a fuck about n…

> Just get the national government to distribute RSA USB keys to every citizen. I lived in a country that did exactly that. And it was a disaster. The keys were trivially easy to steal, even by accident (personal experience here), and you still have the same trust problem as before, except that with a central authority now you do not have as much control. I have also used the electronic-signature-comes-with-your-ID-c…

Interesting.

If you don't mind me asking, what country?

Re: I'm giving up on PGP

#315

Post by bigbugbag »

lbenes wrote: post #193
dom0 wrote: post #32

Earlier quoted context omitted.

> I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here. I don't think the "WoT" is conceptually flawed, and frankly, the argument that "people of average intelligence" can't grasp the concept comes from a very high horse and is also untrue. It's simply that any and all software for PGP utterly fails in the UX and functionality department when it comes to key management. Web of Tr…

I worked in IT for an engineering company that required all external emails to be PGP encrypted. Despite all engineers having Symantec PGP software installed and setup, training, and support of IT, they would often ignore this policy. The excuse, often valid, was it would require IT from both companies to setup the encrypted keys for the first time for new users. If the system is too complex for engineers, the idea o…

> PGP needs to be as simple as the SSL Lock in a browser if there is to ever be any hope of widespread adoption.

Something like the level of confidentiality feature in (soon to be) caliopen[1]:

>> What is behind the idea of confidentiality level?

In Caliopen, every element has its own "confidentiality level" which tells the user what is the security level for any contact or message or conversation...

Each terminal declared by the user is graded according to its use (e.g. strictly personal, at home or as a public access within the enterprise), its type (a phone is necessarily less secure than a desktop PC, as it is much easier to loose). When used for the first time, a non declared terminal receives a note of zero.

Incoming messages are rated whether they are or not encrypted, and also according to the type of encryption key. The type of transport (secured or not) influences the rating as well as confidentiality level associated to the related contact if it is known. The algorithm that rates a conversation is more complex, but takes into account all described elements.

For a user's contact, the confidentiality level is equal to the global confidentiality level of this contact's account: this global confidentiality level is the only public element of a CaliOpen account.

Finally, every CaliOpen instance should eventually geWhat is behind the idea of confidentiality level? [1]: https://caliopen.org/

Re: I'm giving up on PGP

#316

Post by mkesper »

caf wrote: post #241
DigitalJack wrote: post #219

Earlier quoted context omitted.

I hate color coding. I'm in the 8-12% of men that have red-green deficient vision. You can use 10% as a rule of thumb. If I'm not mistaken in my probability math, that means in a group of 5 men, there is a 50% chance one of them is "color blind." Yet the world insists on using red/green as bad/good indicators. Drives me nuts.

You are mistaken. If probability of each of the 5 men being colorblind is independent (so eg. they're not related etc), then there's a 41% chance that at least one of them is (1 - 0.9⁵). (There's a 33% chance that exactly one of them is: 0.1 × 0.9⁴ × ⁵C₁).

That's not soo much lower, though.

Re: I'm giving up on PGP

#317

Post by NoGravitas »

kkl wrote: post #71
NoGravitas wrote: post #45

Earlier quoted context omitted.

Signal is nice, and I use it. But it's an instant messaging system. Email has different use cases. I think what we're going to need is a new, non-SMTP protocol, which preserves all of the good things about email, while providing e2e encryption and (pseudonymous) identity assurance. I don't know enough to be involved in designing that protocol, though, other than saying what I want to see as an end-user.

What properties does email have that asynchronous messaging services (e.g. Signal) do not?

There are protocol properties, and client properties. I think some of both are important.

### Protocol

* Easily federated

* Identifiers can be memorable/meaningful (unlike phone numbers) while still being globally unique (thanks to federation)

* Device independent (not tied to a phone number, can generally use the same account on different devices)

* Can contact people you don't know/haven't met (this is possible with Signal, but they'd have to publicly share their personal cell phone number, which is a no-go).

### Client

* Optimized for longer-form, less immediate messaging (folders, drafts, rich text)

* MIME attachments (Signal supports only a limited number of predefined types of attachments)

I feel like you could probably layer an email-equivalent on top of Matrix, but I'm not 100% sure about that.

Re: I'm giving up on PGP

#318

Post by NoGravitas »

psiconaut wrote: post #57
NoGravitas wrote: post #45

Earlier quoted context omitted.

Signal is nice, and I use it. But it's an instant messaging system. Email has different use cases. I think what we're going to need is a new, non-SMTP protocol, which preserves all of the good things about email, while providing e2e encryption and (pseudonymous) identity assurance. I don't know enough to be involved in designing that protocol, though, other than saying what I want to see as an end-user.

pond has interesting properties, I think the next generation mail will have to implement some of those ideas. and Signal/WhatsApp comes to replace (and kill) xmpp, not email. Another issue is the generational shift away from email, that is only for Spam and Work, more and more everytime...

Since Pond is hard to search for, [link attached][0].

[0]: https://github.com/agl/pond

Re: I'm giving up on PGP

#319

Post by matheusd »

user5994461 wrote: post #209
dom0 wrote: post #32

Earlier quoted context omitted.

> I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here. I don't think the "WoT" is conceptually flawed, and frankly, the argument that "people of average intelligence" can't grasp the concept comes from a very high horse and is also untrue. It's simply that any and all software for PGP utterly fails in the UX and functionality department when it comes to key management. Web of Tr…

I have to partially disagree with that. Calling PGP an utter failure is an understatement. Just like calling a cat a small tiger. PGP is possibly the WORST experience in usability for any well known software that ever lived. This thing should be taught in courses for decades to come as how to fail a product by 1) having no UI 2) no integrations with anything 3) zero usability 4) not even trying to give a fuck about n…

Brazil is heading in that direction.

Every single corporation here and even freelance service workers are required by law to have a key/certificate pair to be able to do file taxes.

Pretty much every single commercial transaction is signed with a certificate.

It is not yet required for every individual citizen to have one, but everything points to that happening at some time in the future.

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