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Convenient End-To-End Encryption for E-Mail

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121–130 of 190 posts

Re: Convenient End-To-End Encryption for E-Mail

#121
post #8

Unpopular but very probably true fact: email can't practicably be made secure, and people should stop trying. Email is itself archaic, and there aren't good reasons people should use it for routine peer-to-peer communications that need secrecy. Why? Because: * It's default-plaintext. We don't generally love the way websites ensure they're viewed securely, but email doesn't even have the basic mechanisms HTTP has to p…

> and instead just get people to adopt serious secure messengers

And here is the main issue, they don't substitute email:

- Async

- Allowing long form text/attachments

- User friendly address (phone numbers are not very easy - we just got accustomed)

- Threaded and archivable conversations

Re: Convenient End-To-End Encryption for E-Mail

#122
post #77

Earlier quoted context omitted.

I agree with you on everything here except for your "don't use email" point in the followups. For 99+% of people, being able to recover your archive when you forget your password or lose your device is more valuable than being secure against a state-level adversary. I think the security debate around email suffers from an over-supply of confidentiality absolutists, in which both integrity and availability take the ba…

Indeed just getting most senders and servers to use TLS would be a good start. That said, lots of businesses deal with sophisticated attackers who are trying to steal trade secrets, patents in progress, etc. Sometimes these attackers are state sponsored too (I would definitely suspect China, US and Russia for this kind of crimes).

Most email on the Internet today does use TLS at present. Google's Safer Email transparency report includes metrics for the rates of inbound and outbound email encryption at Gmail, and both are about 90%.

These days all major providers and software support TLS and will employ it by default. (There are some holdouts though, just like for HTTP.)

[1] https://transparencyreport.google.com/safer-email/overview

Re: Convenient End-To-End Encryption for E-Mail

#123
post #57

Earlier quoted context omitted.

Oh look, another "middlebrow dismissal" ( https://news.ycombinator.com/item?id=4693920 ) upvoted to the top of a HN post. Color me surprised.

Using the terminology of your link, tptacek is not "slightly more than unsophisticated" wrt security. Dismissive, sure, but "middlebrow" it is not. I like that term, and I don't want it to turn into a generic, meaningless slap like "fascist" or something. And it's worth taking seriously any comment about security on HN when we're lucky enough to get one by an expert, whether it's tptacek, moxie, cperciva, the profess…

> the professor who goes by his initials

djb?

Re: Convenient End-To-End Encryption for E-Mail

#124
post #112

Earlier quoted context omitted.

I have colleagues and students that don't use smart phones. As much as I agree with your sentiment, the unfortunate truth is that right now there isn't a good drop in replacement that we could move to. Signal is drop in for WhatsApp and I can tell everyone I talk to on WhatsApp to just contact me on Signal instead. What do I tell people to move to from EMail?

WhatsApp is an ok substitute for Email in my opinion. Sure, it is not open source and but federated. Signal, Wire, Matrix, etc should catch up in the next years. What do you need from Email that a messenger lacks?

> What do you need from Email that a messenger lacks?

Discussion threads. Say I work on two different projects with the same colleague, or that I am also friends with a coworker and do things together outside of work. In whatsapp the different topics would all be mixed together into a big mess. With email I can just reply to a particular thread.

Re: Convenient End-To-End Encryption for E-Mail

#125
post #124
post #112

Earlier quoted context omitted.

WhatsApp is an ok substitute for Email in my opinion. Sure, it is not open source and but federated. Signal, Wire, Matrix, etc should catch up in the next years. What do you need from Email that a messenger lacks?

> What do you need from Email that a messenger lacks? Discussion threads. Say I work on two different projects with the same colleague, or that I am also friends with a coworker and do things together outside of work. In whatsapp the different topics would all be mixed together into a big mess. With email I can just reply to a particular thread.

I prefer Telegram now but this should work in Whatsapp as well:

Just create a group for each context and name them properly.

Re: Convenient End-To-End Encryption for E-Mail

#126
post #115
post #32

Earlier quoted context omitted.

> It's that we should stop using email pretty much altogether. Like I said: it's archaic Sorry but have you ever used Signal or any other IM to send anything longer than a few sentences? Email can be as long as you want, and it is totally appropriate when you want to write a longer document.

How often do you send emails longer than a few sentences? I don't really see a problem with long messages on Signal. The only annoyance is that the desktop clients are always browser-based (Electron or website or plugin).

> How often do you send emails longer than a few sentences?

Actually every single day, and not just once. Maybe I am an outlier?

Re: Convenient End-To-End Encryption for E-Mail

#127
post #124
post #112

Earlier quoted context omitted.

WhatsApp is an ok substitute for Email in my opinion. Sure, it is not open source and but federated. Signal, Wire, Matrix, etc should catch up in the next years. What do you need from Email that a messenger lacks?

> What do you need from Email that a messenger lacks? Discussion threads. Say I work on two different projects with the same colleague, or that I am also friends with a coworker and do things together outside of work. In whatsapp the different topics would all be mixed together into a big mess. With email I can just reply to a particular thread.

Huh, i think you've just identified (for me at least) the crux of the issue.

What messaging system other than email allows for topic based discussion? I guess you could abuse groups to donsomething similar, but its not wuite the same.

The underlying one person to one person philosophy of messaging apps is infuriating for organised discussion over time. It makes finding info discussed harder too.

Does anyone have any suggestions for messaging apps that don't put person to person front and center but topic discussion like email?

(You might argue the last point i made there, but go and make two separately stored discussions with the same person on whatsapp or signal or wharever... I'll wait).

Re: Convenient End-To-End Encryption for E-Mail

#128
post #5
post #3

Here is a description how it works: https://posteo.de/en/blog/new-easy-email-encryption-with-aut...

>>The manual exchange and management of keys – which users often perceive as complicated – is becoming superfluous: Prior to the first encrypted communication, a regular empty email (without content) is sent. With this, the key is transferred in the background. Henceforth, messages can be encrypted automatically. doesn't sound like they solved the key exchange problem. they merely changed it to trust on first use.

And that still defends against the biggest howler with email, that in raw form it is a post card, not a enveloped letter.

The issue if trusting that the sender is who is being claimed is a very different issue, and one that i don't think anyone had solved yet beyond cumbersome exchange procedures (possibly involving locked suitcases).

Re: Convenient End-To-End Encryption for E-Mail

#129
post #8

Unpopular but very probably true fact: email can't practicably be made secure, and people should stop trying. Email is itself archaic, and there aren't good reasons people should use it for routine peer-to-peer communications that need secrecy. Why? Because: * It's default-plaintext. We don't generally love the way websites ensure they're viewed securely, but email doesn't even have the basic mechanisms HTTP has to p…

> Unpopular but very probably true fact [...]

That's not a fact. That's a conclusion based on the premises you put forth. You should put the conclusion on the bottom of your post. Now it is akin to a forecast or fortune-telling. There's no need to resort to such strong language in an otherwise decent post. Your premises don't need it, and your argument doesn't need it either. If you worded your post slightly less bifurcating it would've been an excellent post without sparkling the controversial discussion.

As for your premises,

> Email leaks metadata. [...]

Agreed, but

> stuff like subject lines are simply content.

Its optional content because if sender wants it to be gibberish or deceiving, that's possible.

> * Most email users get their email from a website. Unless you make them install something on all their computers

That's a matter of RFCs and implementing the new technology in client and server. If we follow your reasoning, we'd still be sitting in the previous century in old standards "because the poor users must upgrade their software."

For the other premises (such as for example "It's default-plaintext."), can you demonstrate it is impossible to fix these issues? Because I don't see that being taken into account. What I see is: "let us break backwards compatibility and switch to this here which is better" but without authority to do that for a significant amount of users we're left with the practical situation of a chicken-egg problem of a defacto standard. And could you actually directly quote from the article what and why is not feasible instead of a general dismissal? The latter feels like a rant the former feels like an in depth discussion. Someone could've written a rant like that about DNS (because IPv4), or about TCP because BGP, but what we need is solutions. IPv4 is an interesting discussion because of IPv6. Its a recent, significant example of the chicken-egg problem of an inferior standard, backwards compatibility, and how to make the switch.

Re: Convenient End-To-End Encryption for E-Mail

#130
post #8

Unpopular but very probably true fact: email can't practicably be made secure, and people should stop trying. Email is itself archaic, and there aren't good reasons people should use it for routine peer-to-peer communications that need secrecy. Why? Because: * It's default-plaintext. We don't generally love the way websites ensure they're viewed securely, but email doesn't even have the basic mechanisms HTTP has to p…

> Most email users get their email from a website. I'd argue thats not the case. Business users are likely still using outlook/etc. Personal users are likely using their smart phone for email. Also by what standard is pgp "the most popular". Its popular with technical people sure, but there is fuck all support in commercial mail clients. S/mime is supported, and due to ca roots, doesnt require you keep using the sams…

Thunderbird and apple mail are both very popular clients that support PGP via plugins.
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