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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#91

Post by tptacek »

Tepix wrote: post #74
pdog wrote: post #72

Earlier quoted context omitted.

Is WhatsApp secure? It's a totally closed protocol owned by a company (Facebook) known for rampant issues with privacy.

Yes with no control over what happens to your key and you don't know if your message has been encrypted after it is sent and by default you aren't even told if the key of your recipient changes.

By making the discredited argument that WhatsApp's key-change behavior is a fatal flaw, you're disagreeing with:

* The EFF

* Moxie Marlinspike

* Matthew Green

* Bruce Schneier

* Isis Lovecruft from Tor

* the grugq

* Matt Blaze

* Avi Rubin

* Steve Bellovin

* Joseph Lorenzo Hall

* Bart Preneel

* Peter Honeyman

* Jon Callas (who cofounded PGP Corp)

* Paulo Barreto

... and about 50 more experts equally respected in the field if less known to the typical HN reader.

Re: Encrypted email is still a pain

#92

Post by wtbob »

tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

> at best you're attempting to tunnel encrypted messaging over an unencrypted transport.

That covers pretty much all communication encryption: ultimately, encrypted data goes out over an unencrypted link.

> A protocol that leaks metadata, including some message content, at the envelope layer.

That is indeed the major problem I have with it.

> Hundreds of millions of users that primarily access messages through browser clients that can't meaningfully implement crypto.

The solution IMNSHO is to get off of the browser. Browsers are great for what they were designed for, but they're a terrible general-purpose computing platform.

> End user demands for things like search that can only be delivered efficiently at scale by databases of plaintext (most likely at centralized servers).

I think that one's home computers can probably handle the load of searching all of one's own data. If that's not the case, encrypted search protocols may be of use.

In general, though, your last point argues against any encryption or other user-privacy measure: if users are right when they demand centralised search, then encryption is a bad thing. I don't agree that encryption is a bad thing, thus I refuse to believe that users are right to demand centralised search.

> But: why bother? Email is just one of dozens of messaging systems available to Internet users.

It's the only decentralised one atop which a trustworthy system could be built. Signal, WhatsApp & Wire all have critical flaws which prevent their widespread use (Signal is centralised, tied to a phone number, leaks contact information to OWS; WhatsApp is centralised, owned by Facebook & default insecure; Wire looks appealing, but it too is centralised and controlled by a single company).

I tend to agree with your conclusion that email encryption is not worth the trouble; I disagree that it cannot be used securely.

Re: Encrypted email is still a pain

#93

Post by tptacek »

mikecb wrote: post #87
lmm wrote: post #60

Earlier quoted context omitted.

Plaintext email doesn't resist state-level adversaries. Email with OpenPGP does.

If you are an active target of a tier 1 state, your endpoint will be compromised, your decrypted communication will be read, and no cryptosystem will prevent this.

Furthermore, if you're using PGP to evade a state-level adversary, the odds are overwhelming that you've own-goaled yourself many times over:

* You keep plaintext archives and drafts of your messages, because that's a fundamental feature of email clients going back 3 decades.

* You use a server-mediated PGP provider like Protonmail that has your security one surreptitious Javascript injection on an XHR call away from complete collapse.

* Your peer accidentally forgot to encrypt a response and quoted your own plaintext back to you.

These things aren't intrinsic problems of encrypted messaging systems, which is something I feel like HN is not doing a good job of grokking. They're intrinsic problems of email.

Re: Encrypted email is still a pain

#94

Post by FabHK »

guenp wrote: post #2

https://gpgtools.org/ works great for Mac.

It does work well, except when there's a macOS major version bump (10.9 -> 10.10 -> 10.11 etc.).

Then you update your system (maybe after a prudent 3 week wait) and everything works, except the GPG Suite, and you can't send encrypted emails for a while, nor can you read ones you receive, or old ones stored locally.

(For macOS 10.12 sierra, released 2016-09-20, there's now a beta of the GPG Suite, released 2017-01-23, 4 months later.)

There was also a bug (or feature?) a while ago where email drafts that you had open in windows would vanish after a while.

It is a good solution for the Mac, but this is something to be mindful of (and it sort of supports the main thrust of the article).

Re: Encrypted email is still a pain

#95

Post by lmm »

mikecb wrote: post #87
lmm wrote: post #60

Earlier quoted context omitted.

Plaintext email doesn't resist state-level adversaries. Email with OpenPGP does.

If you are an active target of a tier 1 state, your endpoint will be compromised, your decrypted communication will be read, and no cryptosystem will prevent this.

There are a large number of other things we need to fix to make individuals able to resist state attackers, sure. We need much better software security in general, more transparency around firmware.... Still, good crypto makes attacking more costly, even for states. My sense is that the cost of attacking someone using email and OpenPGP will be higher than for any existing alternative (including WhatsApp/Signal), at least for an adversary with the US security services onside.

Re: Encrypted email is still a pain

#96

Post by tptacek »

lmm wrote: post #89
tptacek wrote: post #64

Earlier quoted context omitted.

That's exactly the point. Take a step back and think about what you just said. It's true: most people don't care about crypto. But here's are two other true statements: * In modern messaging protocols, they don't have to care about encryption. The protocols are designed to reliably encrypt messages without user intervention, and security isn't "opt-in". * The people who most need encryption are not the ones who are m…

> In modern messaging protocols, they don't have to care about encryption. The protocols are designed to reliably encrypt messages without user intervention, and security isn't "opt-in". Sounds good. Doesn't sound worth giving up decentralisation for. Doesn't even seem like something we'd need to give up OpenPGP to get - if client design were equal (and it isn't at the moment, but I see no reason it can't be) I'd far…

There are also people that use OpenOffice on Desktop Linux, and believe in their bones that everyone else should too.

Re: Encrypted email is still a pain

#97

Post by Cyph0n »

mikecb wrote: post #87
lmm wrote: post #60

Earlier quoted context omitted.

Plaintext email doesn't resist state-level adversaries. Email with OpenPGP does.

If you are an active target of a tier 1 state, your endpoint will be compromised, your decrypted communication will be read, and no cryptosystem will prevent this.

And if you were aware that a state-level actor is targeting you, you'd be using a programmable, self-contained HSM for all sensitive computation. This is a topic I'm working on actually.

Re: Encrypted email is still a pain

#98

Post by tptacek »

wtbob wrote: post #92
tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

> at best you're attempting to tunnel encrypted messaging over an unencrypted transport. That covers pretty much all communication encryption: ultimately, encrypted data goes out over an unencrypted link. > A protocol that leaks metadata, including some message content, at the envelope layer. That is indeed the major problem I have with it. > Hundreds of millions of users that primarily access messages through browse…

You're disagreeing with an argument I didn't make. "Cannot" isn't the word I would choose.

Re: Encrypted email is still a pain

#99

Post by twsted »

tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

> Better to move sensitive conversations to things like Signal, WhatsApp, or Wire

Really? Come on!

WhatsApp is owned by a company whose business is done by retrieving all the information it can from users and by tracking their behaviors.

Re: Encrypted email is still a pain

#100

Post by mnw21cam »

cyphar wrote: post #35
parennoob wrote: post #16

Do any of these keyservers perform email verification? It would go a good way towards some kind of verification that a user's GPG key corresponds to their email. Otherwise, anyone can generate a key with any email address and push it up to the servers. The standard way of verifying it (key-signing parties) is somewhat difficult.

Making users assume that emails are in _any way_ verified is dangerous because it is far too low of a bar to provide any practical security for PGP keys. Not to mention that PGP keys can be used outside the context of email (so the email could be empty or otherwise incorrect).

Agreed. The keyservers are public posting boards. You are meant to verify that the key is sufficiently signed in a chain all the way to yourself before you trust it. Anything on the keyservers that makes people think the key has already been verified is a bad thing.
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