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Backwards compatibility is the killer. The whole design of PGP is to be the envelope to make email private, versus the plaintext postcard that everybody can re
by Decade 11y ago
Backwards compatibility is the killer.
The whole design of PGP is to be the envelope to make email private, versus the plaintext postcard that everybody can read. It works with existing servers and existing mail clients.
The biggest Snowden revelation is the importance of metadata. Just knowing whom you talk to, when, is frequently enough to compromise the parties involved. You might be doing something legal now, but you can’t tell when some despot takes over and makes your activity illegal. When data can potentially last your lifetime, you need to consider this sort of thing. Illustration: Using Metadata to find Paul Revere. [1]
So, we need a new mail transmission protocol that limits the amount of metadata that can be seen. Something like Dark Mail [2]. I don’t think Open Whisper Signal hides the metadata.
The problem is that Dark Mail needs to be developed and its security reviewed, and people need to adopt it. It needs new servers and clients, and the prevalence of Windows shows just how difficult that problem is. Also, any new messaging program these days needs a story about web and mobile.
In practice, I heard someone say that the biggest improvement in people’s privacy has been use of Gmail. The clients connect to it with SSL certificates controlled by Google; Google promotes 2-factor authentication and access tokens; and Google’s legal team challenges subpoenas. As long as you are not leaking national security secrets, I think this is adequate until a better system is deployed.
[1] http://kieranhealy.org/blog/archives/2013/06/09/using-metadata-to-find-paul-revere/ http://kieranhealy.org/blog/archives/2013/06/09/using-metada...
[2] https://darkmail.info https://darkmail.info
- baudehlo 11y agoSMTP with TLS doesn't leak any metadata except the connecting IP address. And with DMARC you can mandate it. Calls for whole new protocols for email are usually made by people who don't understand the email ecosystem as it currently stands.
- function_seven 11y agoCan the TLS be enforced by the sender all the way through the chain to the destination mailbox?
- evook 11y agoYes, as well as PGP or S/MIME. It just depends or your relay configuration. We've implemented it switch able. We've customers that are bouncing non PGP encrypted E-Mails.
- Arnt 11y agoThe sender (the sender's service provider or organization) decides when to use TLS while the message bounces around internally, then (this is the typical long hop) the recipient's server and the sender's SMTP client negotiate, and then the recipient gets to decide. The sender may have opinions, but as soon as the message is handed over to the recipient's server, that's it. That's the end of the sender's influence, and that's how it has to be on a global internet. People can connect without having their infrastructure approved by anyone else.
- gnaritas 11y agoNo, it can't. The receiver could be using a non secure SMTP server.
- cbhl 11y agoBut SMTP with TLS is opportunistic -- and if we're talking "national state secrets" it's trivial for a state to MITM the connection and do a TLS downgrade attack.
- Spooky23 11y agoIf you actually care about the data, it does nothing. It only guarantees that the front door is encrypted. With the number of cloud anti spam and archive companies out there, you have no idea what happens between those providers and the mail servers.
- acqq 11y ago> In practice, I heard someone say that the biggest improvement in people’s privacy has been use of Gmail. In practice, until Snowden happened, NSA was able to access all the Google's internal data as Google replicated in plaintext its whole datacenters through the links snooped by the NSA or the GCHQ. http://www.slate.com/blogs/future_tense/2013/10/30/nsa_smiley_face_muscular_spying_on_google_yahoo_speaks_volumes_about_agency.html http://www.slate.com/blogs/future_tense/2013/10/30/nsa_smile...
- late2part 11y agoCorrect. And now they encrypt all the inter-data center traffic. Question: Is that done on an end-to-end basis? Or do they encrypt the links between data centers? I want to encrypt a 10g ethernet and all the solutions look quite expensive. Has anyone done high speed encryption (i.e. 10gbps/1500 byte packets) with strongswan or similar?
- acqq 11y agoI believe end to end is simpler when you control all the ends and can tweak all the software, like they do. There's also an advantage of having very fast processors already provided.
- nocarrier 11y agoYou have to encrypt the transport at the application layer when you're talking about the scale of major internet companies--there are so many links going out of each datacenter that it's not feasible to do IPsec or similar lower level encryption. There aren't many hardware devices sold that can do the encryption at the 10-100+ Gbps speeds that datacenter links use (if any), and it's much easier to amortize the encryption cost across all your application cpus versus having a small number of devices or dedicated hosts doing crypto at a lower layer.
- Sephr 11y ago> There aren't many hardware devices sold that can do the encryption at the 10-100+ Gbps speeds You are vastly underestimating AES-NI. Most modern Intel CPUs can handle that kind of encryption throughput (when paired with fast enough memory). Even my old Sandy Bridge-E CPU from 2011 gives me ~96 Gbps of AES throughput (with quad channel memory).
- nailer 11y agoAnyone on HN know what Signal does for envelope encryption? AFAICT it's the only crypto app that's OSS and still cares about usability.
- mikeokner 11y agoI'm reasonably certain all communication with the routing servers is done via https. You could double check their source on GitHub
- MichaelGG 11y agoDark Mail turned out to be a joke. Apart from the silly fields like "political party", the fundamental security model's broken. It has essentially zero benefits of "just use Gmail". The suggested security level delegates security to the receiver's mail server. Basically if we just had a " require TLS with verified cert for SMTP" option, that'd do most of what Dark Mail does. In fact, big companies already so this. When LM talks to the DOD over SMTP, you can bet they have mandatory TLS. Exchange offers this out of the box. DM offers higher capabilities with no usability benefits over PGP or whatever. Disclaimer: Since the beginning, I've said the DMA had a zero chance of success. The problem isn't solvable.
- aevernon 11y agoIn these discussions about the importance of metadata, I'm surprised that Bitmessage is rarely mentioned. The Bitmessage protocol is decentralized, trustless, and hides metadata such as the sender and receiver of messages.
- tmalsburg2 11y agoI was really excited when I first read about bitmessage. As far as I can tell, it solves more problems than any other messaging protocol. It's a mystery to me why is doesn't get more attention.
- Spooky23 11y agoI can't agree with this assessment. Personally, the NSA or pervasive surveillance use case is overblown and a low risk threat to me. Anyone reasonably competent conducting the most cursory of investigations could figure out who I do business with in hours. The NSA boogeyman with omniscient network surveillance capability will come up with ways to find the source/destination of obfuscates messages anyway. Sensitive data that I routinely handle is content. Employees improperly reading mail (on either sender or recipient side), or some data breach affecting mail servers, desktops, or relays are much higher risks. PGP is a great way to encrypt ad hoc data at rest. I think the reason it isn't pervasive is that once you figure out what is really secret, you develop specific tools to transmit that data more seamlessly.
- will_pseudonym 11y agoWhat about the chilling effect? People change their behaviors when they know they're being watched. It goes completely against the spirit of the US Constitution. How can I pursue happiness if I'm worried that what I write will be a liability in the future? EDIT: grammar
- Spooky23 11y agoI disagree with the surveillance society, but I can't control that policy. So I choose to focus on what I can control.
- deleted 11y ago[deleted]
- will_pseudonym 11y agoI absolutely agree with "focus on what you can do." I think that we can also engage in the conversation as a community and network, which of course you are doing. The main thing that stuck out to me about your post was "low risk to me." I have studied risk extensively, and I would like to point out that generally, risks are classified with ratings of both frequency and severity. I would categorize the NSA spying as moderate-high risk (to you) due to their extremely high frequency. Yes, the severity to you will be relatively moderate (chilling effect, etc), but the cumulative, unrelenting effect it has is incredible. As I'm thinking about this more, it's not even a true "risk," because risk always entails uncertainty. You are certainly being affected by it. The true risk of the spying program is that somehow you are hung by your own words, which has an extremely high severity (prison aka slavery). I hope that this rings true to you. Rereading what I've written, it seems like I could be projecting a lot of my own feelings and experiences onto you, but this stuff is just so universal in its effects. Thanks for discussing this! Have a great day.
- cbsmith 11y agoWe've had mixminion[1] around for years, which handles backwards compatibility with aplomb. [1] https://github.com/mixminion/mixminion/ https://github.com/mixminion/mixminion/
- XorNot 11y agoBackwards compatibility has nothing to do with it. No one can read GPG encrypted mail. It isn't built into their clients, they don't by default get their own keypairs, it is simply straight up impossible to send encrypted email to even friends and family and have them be able to read it. Everything else is window dressing to this problem.
- sigjuice 11y agoHow about S/MIME? At least, the programs that I use on a regular basis have it built in. (iOS and OS X Mail, Thunderbird, Outlook). It still does not help at all with the management and distribution of key pairs.
- kristopolous 11y agoMy idea has been to have a system that works on top of email but sends out "fraud" email to other participants in the network. The encrypted payload gets unencrypted at each endpoint and has a marker as to whether it was, what i call a "fuzzer" email, in which case it's discarded - otherwise it gets graduated to the users inbox. Under this system, Eve will see Alice exchanging encrypted messages with Bob and Carol but won't know if they're automated dummy messages or authentic communication. It lowers the information fidelity through an intentional introduction of noise. The "fuzzing model" has wide use cases: for instance, a web browser can programmatically "browse" a variety of websites so that Eve can't tell what Alice is truly looking at. Every user in a system will have "red flag" websites in the "auto browse" list.
- joesmo 11y ago"In practice, I heard someone say that the biggest improvement in people’s privacy has been use of Gmail" Technologically that might be true, but since Google is a third party they're required to provide their data to the government so practically, the technological considerations like SSL are absolutely meaningless.