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How to make e-mail encrypted for everyone

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Re: How to make e-mail encrypted for everyone

#11

Post by hannob »

EmilStenstrom wrote: post #6
vbit wrote: post #2

> When you send an e-mail today it’s sent in plaintext. This means that when you connect to your local coffee shop’s WiFi they can intercept all e-mail that is sent through their router. This is probably not the relationship you have with your barista… Um, how many users use native clients on unencrypted ports as opposed to https based web-clients or TLS?

I don't have any stats, but I imagine lots of users still connect over unencrypted ports directly to their ISP. We have to remember that most users are not like the HackerNews demographics. If you have stats that points to this conclusion being wrong I'm happy to change my mind.

Fortunately most ISPs and mail providers have disabled unencrypted logins. And many mail clients give really scary warnings if you try to use unencrypted imap or pop3.

Re: How to make e-mail encrypted for everyone

#12

Post by nickpsecurity »

EmilStenstrom wrote: post #7
hannob wrote: post #4

DNS-based key discovery has already been invented twice: PKA and OPENPGPKEY. Nobody is using it. It has an obvious problem: DNS is not secure. There is DNSSEC, but it's practically undeployed on clients, therefore building on it doesn't make sense. GPG recently added support for key discovery via HTTPS (Web Key Service, WKS). That goes in the right direction, because it takes the best deployed working authentication…

I don't think this is about inventing a new protocol. It's about getting Gmail and Thunderbird on board. Has anyone put them in a room together?

https://thehackernews.com/2014/12/gmail-end-to-end-encryptio...

https://www.enigmail.net/index.php/en/

I haven't seen them in a room together but they each have something available. Making it Chrome/Gmail extension, Firefox plugin, and Thunderbird Enigmail interoperable may go a long way. Still UI issues and apathy that will hurt uptake. To start with.

Re: How to make e-mail encrypted for everyone

#13

Post by Matt_Cutts »

EmilStenstrom wrote: post #6
vbit wrote: post #2

> When you send an e-mail today it’s sent in plaintext. This means that when you connect to your local coffee shop’s WiFi they can intercept all e-mail that is sent through their router. This is probably not the relationship you have with your barista… Um, how many users use native clients on unencrypted ports as opposed to https based web-clients or TLS?

I don't have any stats, but I imagine lots of users still connect over unencrypted ports directly to their ISP. We have to remember that most users are not like the HackerNews demographics. If you have stats that points to this conclusion being wrong I'm happy to change my mind.

It looks like 80-85% of emails to/from Google are encrypted in transit, according to this page: https://www.google.com/transparencyreport/saferemail/

Encryption at rest is still a difficult UX/UI issue, but encryption during transit seems like something that most mail providers can get behind.

Re: How to make e-mail encrypted for everyone

#14

Post by nickpsecurity »

It's not going to work. All the main problems must be overcome in theory and practice before it gets deployed. Here's a summary of them from Collin Robbins:

https://cybermatters.info/2012/08/13/why-has-encrypted-email...

Note: He was one of LDAP's inventors. His company Nexor deploys both encrypted mail and high-security guards regularly. That's his credentials.

Re: How to make e-mail encrypted for everyone

#15

Post by mjevans »

The two biggest detraction points are completely valid:

1) The need to install ANY (non-standard) software (by definition -everyone- should already be able to use it).

2) The need for users to manage their own keys.

I envision a solution to point 1 is making it a /feature/ of every OS to implement the required software for the open protocol. Prototype on BSD/Linux, get MacOS to ship slick versions of the protocol, and use THAT to club Microsoft over the head for also shipping support with Windows.

Paired with point 1, smart USB attached keys. End users should think of that as their signature and their 'mark' for signing official legal things and literally inking a document with blood.

The USB key should at least have a few lights as an indicator and a couple of buttons.

It should be easy for the user to:

* Allow it to AUTHENTICATE a provided datastream.

* Allow it to decode and provide the unlock key for a datastream back to the computer.

* Allow it to provide a signature for a datastream.

I order those in the least to most trusted operations it should perform.

It might, for a smarter device, support multiple keys or different trust levels of keys.

With the above two frameworks in place all other problems become /far/ easier to solve, and the user experience will be much better (so it'll actually /happen/).

Re: How to make e-mail encrypted for everyone

#16

Post by jcranmer »

The goal of encryption in email boils down to preventing your email provider from being able to read the email. (If you don't want to prevent that, then your email is already encrypted from everyone else if you and your recipient uses SSL and you use major email providers that try SSL over the internet backbone). Keeping your email provider away means your email provider can't have your private key, which means you need some way to keep the key in sync between different email clients--say desktop and smartphone.

Re: How to make e-mail encrypted for everyone

#17

Post by jcranmer »

Matt_Cutts wrote: post #13
EmilStenstrom wrote: post #6

Earlier quoted context omitted.

I don't have any stats, but I imagine lots of users still connect over unencrypted ports directly to their ISP. We have to remember that most users are not like the HackerNews demographics. If you have stats that points to this conclusion being wrong I'm happy to change my mind.

It looks like 80-85% of emails to/from Google are encrypted in transit, according to this page: https://www.google.com/transparencyreport/saferemail/ Encryption at rest is still a difficult UX/UI issue, but encryption during transit seems like something that most mail providers can get behind.

Note that this is MX-MX routing of emails between email providers, which sort have has to allow plaintext in practice.

The question of user-level IMAP/POP/SMTP access is different, but I'd expect somewhere in the region of 95+%. Note that the IMAP specification prohibits authentication that sends passwords in the plaintext [1] (although I don't know if the various IMAP servers permit AUTHENTICATE PLAIN before STARTTLS--checking, Outlook doesn't, and the other servers I had access to aren't open on 143 anyways), which means IMAP in practice requires SSL.

[1] The alternative is to use schemes like CRAM-MD5 or SCRAM-SHA-1 which don't send the password in plaintext, although these have become quite rare in practice.

Re: How to make e-mail encrypted for everyone

#18

Post by gruez »

EmilStenstrom wrote: post #6
vbit wrote: post #2

> When you send an e-mail today it’s sent in plaintext. This means that when you connect to your local coffee shop’s WiFi they can intercept all e-mail that is sent through their router. This is probably not the relationship you have with your barista… Um, how many users use native clients on unencrypted ports as opposed to https based web-clients or TLS?

I don't have any stats, but I imagine lots of users still connect over unencrypted ports directly to their ISP. We have to remember that most users are not like the HackerNews demographics. If you have stats that points to this conclusion being wrong I'm happy to change my mind.

...and how many people still use their ISP's mail as opposed to the "big" providers?

Re: How to make e-mail encrypted for everyone

#19

Post by Thespian2 »

Sounds like you are talking about Identity Based Encryption (IBE)

https://en.wikipedia.org/wiki/ID-based_encryption

There are mature, commercial products which use this to address the "PKI benefits without the overhead of managing PKI" problems. Read the wikipedia page for the gory details, but essentially, you get to use someone's email address functionally as a public key (as per traditional PKI email schemes) wihtout the recipient having to, a priori, create the pub/priv keypair. They can be derived statelessly on the fly.

For one example, See Hewlett Packard Enterprise - Data Security "SecurMail" product.

Full disclosure: I work on this product.

Here is some basic background information on how it works.

https://www.voltage.com/products/email-security/hpe-securema...

There is still a "trusted 3rd party" running the key generator (a deal-breaker for some threat models of privacy) but that generator entity doesn't have to be the ISP or email provider involved at either end.

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