6 ms·

It is unlikely that built-in email encryption will ever be available in Gmail

196 points by wil_I_am_27 8y ago

nukeop 8y ago
Advertisement for tutanota. Just use GPG like everybody who knows what they're doing.
politelemon 8y ago
It was dead the moment they put it on Github. Their blog post[1] claimed: > E2EMail is not a Google product, it’s now a fully community-driven open source project, to which passionate security engineers from across the industry have already contributed. But looking at the commit history[2] makes it clear that was not the case at all. Although this post is by Tutanota (and I can't tell if Tutanota supports PGP), Protonmail does support PGP emails. 1: https://security.googleblog.com/2017/02/e2email-research-project-has-left-nest_24.html https://security.googleblog.com/2017/02/e2email-research-pro... 2: https://github.com/e2email-org/e2email/commits/master https://github.com/e2email-org/e2email/commits/master
- coldtea 8y ago
  AKA "death by open sourcing it", the hideous cousin to the equally awful "Death by acquisition" (aka "We will continue working on this now that we've been acquired").
- bad_user 8y ago
  All email services selling encrypted email as a service are snake oil in my opinion. You won't gain anything more than when using GPG by yourself, except you're now trusting a third-party app to do it for you, using a non-standard adapter for allowing IMAP / SMTP apps to still work while at the same time obscuring the fact that end-to-end encryption will only happen when the recipients support it as well, which is at most 1% of all recipients you're communicating with.
Leace 8y ago
The article has a point but do know that Tutanota is using their own custom encryption scheme. I can understand they don't want to support PGP if they have something better but judging from their FAQ [0] they just replicated what PGP already can do [1] [2] effectively reinventing square wheel. As for browser encryption Mailvelope [3] works and can even use local GnuPG (through NativeMessaging). FlowCrypt [4] is a little bit more tightly integrated with Gmail (through their API). [0]: https://tutanota.com/faq/#pgp https://tutanota.com/faq/#pgp [1]: "That's why we have developed a solution that is also based on recognized algorithms (RSA and AES) and that automatically encrypts the subject, the content and the attachments." [2]: https://github.com/autocrypt/memoryhole#memory-hole-protected-e-mail-headers https://github.com/autocrypt/memoryhole#memory-hole-protecte... [3]: https://www.mailvelope.com/en https://www.mailvelope.com/en [4]: https://flowcrypt.com/ https://flowcrypt.com/
- jrochkind1 8y ago
  Hmm. Solutions like signal or whatsapp also used their "own custom encryption scheme" (in that sense), instead of PGP. I'm not sure PGP is actually good enough that alternatives aren't desirable. Here's a Wired article saying "PGP is dead... use Signal for your encrypted messaging instead": https://www.wired.co.uk/article/efail-pgp-vulnerability-outlook-thunderbird-smime https://www.wired.co.uk/article/efail-pgp-vulnerability-outl... Here's respected cryptographer Matthew Green saying PGP is "a model of email encryption that’s fundamentally broken" in 2014. https://blog.cryptographyengineering.com/2014/08/13/whats-matter-with-pgp/ https://blog.cryptographyengineering.com/2014/08/13/whats-ma... I think there was another more recent "what's the matter with PGP" post I saw on HN, I found these above while trying to see if I could remember what I saw more recently.
  - Leace 8y ago
    > Solutions like signal or whatsapp also used their "own custom encryption scheme" (in that sense), instead of PGP. But Signal's "own custom encryption scheme" have obvious advantages over PGP, for example forward secrecy. That's what I meant by "I can understand (...) if they have something better". In Tutanota's case judging from their public descriptions the scheme doesn't have any advantages over PGP as it is currently used. Implementing custom crypto usually ends up with something like this: https://tutanota.uservoice.com/forums/237921-general/suggestions/7858974-tutanota-is-using-unauthenticated-aes-cbc-encrypti https://tutanota.uservoice.com/forums/237921-general/suggest...
tkfu 8y ago
> While it is possible to encrypt certain emails in Gmail with GPG, Google can still read all email meta-data such as email addresses and subject lines. Better use a Gmail alternative that encrypts your entire mailbox and contacts automatically. This is nonsense. Any email service will be able to see the recipients (and senders) of your messages, because that's how email works. Subject lines too, again, because that's how email works. E2E encryption of email is a good thing, GPG is hard. These things have be true forever.
- alfiedotwtf 8y ago
  This. Can we please kill the idea of "safe email" forever. Email leaks like a sieve. In fact, It would be interesting to see if the Carbon Copy (CC:) feature of email violates GDPR.
  - alias_neo 8y ago
    Don't even get me started on domain spoofing. I get so much junk every day due to bounce backs of people spoofing my domain to send junk. SPF, DKIM and DMARC have done (and can do) nothing to help. Email is broken, and this, sadly, is the price we pay for the federation it provides for a technology of its age.
    - simias 8y ago
      Are you sure your server is correctly configured? I host my own server on a custom domain and while I do receive a non-negligible amount of spam I don't think I've ever noticed my domain being spoofed. >SPF, DKIM and DMARC have done (and can do) nothing to help. Isn't that precisely what these technologies are supposed to help? Why do you say that they can't do anything?
      - kikoreis 8y ago
        You are right that they are designed to prevent spoofing. The problem is that the recipient server needs to be configured to use it and not all servers do, for reasons spanning false positives to ignorance. So if you have a fairly old or known domain you will get non trivial amounts of backscatter from spoofed email being sent to invalid or otherwise rejected addresses.
hannob 8y ago
I know it's a bit old, but since I read this I cannot possibly take Tutanota seriously on anything crypto: https://tutanota.uservoice.com/forums/237921-general/suggestions/7858974-tutanota-is-using-unauthenticated-aes-cbc-encrypti https://tutanota.uservoice.com/forums/237921-general/suggest... https://seclists.org/fulldisclosure/2015/Jun/58 https://seclists.org/fulldisclosure/2015/Jun/58
snvzz 8y ago
We need the Dark Mail Alliance more than ever. https://en.wikipedia.org/wiki/Dark_Mail_Alliance https://en.wikipedia.org/wiki/Dark_Mail_Alliance https://darkmail.info/downloads/dark-internet-mail-environment-june-2018.pdf https://darkmail.info/downloads/dark-internet-mail-environme... https://github.com/lavabit/ https://github.com/lavabit/
hguhghuff 8y ago
The problem with Email is that it’s routed, store and forward, whereas there’s no reason why it shouldnt be point to point. If you wanted to revolutionize email then you’d create a point to point email service.
- robjan 8y ago
  That shouldn't be a problem if it's properly encrypted. The whole internet is routed over various switches owned by various entities.
- flurdy 8y ago
  Point to point is very fragile and inflexible. There are many good reasons for email (and internet in general) was designed to be routable.
- krageon 8y ago
  There's a reason peer to peer isn't seen as a great idea for messaging and that reason is it's been tried many, many times and it doesn't work well. For some people it just won't work well ever. Furthermore, it doesn't mesh with the expectations most people will have of a mail service (you push the mail out and it will arrive some day regardless of what you do), which makes it a bad fit for the use-case to begin with.
mikekchar 8y ago
In the meantime I'm using mutt on the desktop on K9 on Android. I have to say that K9 is brilliant (mutt less so, but I like it ;-)). It's the closest "it just works" E2E mail client I've ever used. Unfortunately the reality of PGP is that it's hard for a normal person to use, although I've got my Dad using it for all of our email.
kjar 8y ago
Mass surveillance is kinda Google’s model
yuz 8y ago
This is a promotion article for an end-to-end encrypted mail service called tutanota. They claim that google abandonment of the mail encryption project impiles that gmail encryption will necessarily never be available for gmail users.
vlastik 8y ago
Why not something like Let's Encrypt, but for S/MIME?
- rtnl 8y ago
  That's actually what a Swiss startup called Vereign seems to be working on: https://medium.com/@ggreve/nobody-cares-about-signatures-a56505b8ce04 https://medium.com/@ggreve/nobody-cares-about-signatures-a56...
Causality1 8y ago
"shows where Google's real interests are: Not in protecting their users' private data, but in harvesting it for their own benefit." Well, Duh. That's the deal. "in exchange for this service we will scrape your data in order to serve ads". If you don't like it go somewhere else. Google doesn't owe you a free email service.
rdxm 8y ago
OK, did anyone ever honestly think this would happen? 'Cause if they did that was pretty naive...
chiefalchemist 8y ago
I'm not a fan of email, and not only because of security / privacy. Yes, it's ubiquitous and convenient; and great for quick simple messages. But it's not (in a biz / life context) a project management tool. So aside from "where do you want to go for lunch?" the appropriateness of email breaks down pretty quick. Unfortunately, the habit and convenience not so much so. Ideally, we're nudging towards a tipping point where email gets replaced by more appropriate (planning and proj management) tools - even at the personal level.
- arbitrage 8y ago
  I'm not a fan of cars, because they don't perform well in lakes. I'm hoping we're moving toward a world where we use different tools for different tasks. Something engineered to float would be much better, in my opinion.
  - chiefalchemist 8y ago
    Yes! Thank you for proving my point[1]!! That is, at this point email is the internet equivalent of a fax machine. It's a hammer (or car) that most are using as a screwdriver (or boat). Factor in the lack of security / privacy and email should be marginalized, just as the fax machine was. [1] Yes, I realize it was not your intent. But the fact is, your analogy is a good one for the point I'm trying to make.
stirfrykitty 8y ago
If all one wants to do is communicate securely with another person and what your typing is private but not "illegal", then why even send email. Simply use the Drafts in GMail. Compose an email and leave it in Drafts. Each person amends the draft and they can agree on times to check and update. This has been done with great success before if you want nothing "going across the wire" so to speak.
LinuxBender 8y ago
GPG is hard for some, but 7-zip is easy for most. Not perfect, but perfect is enemy of good. Just put your email, files, whatever in a 7-zip encrypted and compressed file and email that. Tell your friend the password over voice chat, or some other chat that is in no way related to your mail provider. Even a weak password is better than trusting the mail provider to handle this job. Here is a 7-zip file with a very simple password. [1] Please reply with the contents of the text file in the 7z. [1] - https://tinyvpn.org/5/e/f/5efed61e6efe235d965547999292279e.7z https://tinyvpn.org/5/e/f/5efed61e6efe235d965547999292279e.7...
jimnutt 8y ago
So, I'm sure this idea has holes all over it, but how about a very simple service that you log into with your PGP public key, then would allow you to post encrypted messages to other PGP public keys and retrieve messages posted to your public key. It could be fully anonymous, depending on your choice of keys. It would be very similar to the mixmaster remailers, except it wouldn't actual mail anything as it wouldn't have any identifiable information other than the public key.
- dredmorbius 8y ago
  PGP itself leaks a huge amount of metadata. A known problem on open mailing lists and Usenet.

196 points by wil_I_am_27 8y ago

Advertisement for tutanota. Just use GPG like everybody who knows what they're doing.

It was dead the moment they put it on Github. Their blog post[1] claimed: > E2EMail is not a Google product, it’s now a fully community-driven open source project, to which passionate security engineers from across the industry have already contributed. But looking at the commit history[2] makes it clear that was not the case at all. Although this post is by Tutanota (and I can't tell if Tutanota supports PGP), Protonmail does support PGP emails. 1: https://security.googleblog.com/2017/02/e2email-research-project-has-left-nest_24.html https://security.googleblog.com/2017/02/e2email-research-pro... 2: https://github.com/e2email-org/e2email/commits/master https://github.com/e2email-org/e2email/commits/master

coldtea 8y ago
AKA "death by open sourcing it", the hideous cousin to the equally awful "Death by acquisition" (aka "We will continue working on this now that we've been acquired").
bad_user 8y ago
All email services selling encrypted email as a service are snake oil in my opinion. You won't gain anything more than when using GPG by yourself, except you're now trusting a third-party app to do it for you, using a non-standard adapter for allowing IMAP / SMTP apps to still work while at the same time obscuring the fact that end-to-end encryption will only happen when the recipients support it as well, which is at most 1% of all recipients you're communicating with.

Leace 8y ago

The article has a point but do know that Tutanota is using their own custom encryption scheme. I can understand they don't want to support PGP if they have something better but judging from their FAQ [0] they just replicated what PGP already can do [1] [2] effectively reinventing square wheel. As for browser encryption Mailvelope [3] works and can even use local GnuPG (through NativeMessaging). FlowCrypt [4] is a little bit more tightly integrated with Gmail (through their API). [0]: https://tutanota.com/faq/#pgp https://tutanota.com/faq/#pgp [1]: "That's why we have developed a solution that is also based on recognized algorithms (RSA and AES) and that automatically encrypts the subject, the content and the attachments." [2]: https://github.com/autocrypt/memoryhole#memory-hole-protected-e-mail-headers https://github.com/autocrypt/memoryhole#memory-hole-protecte... [3]: https://www.mailvelope.com/en https://www.mailvelope.com/en [4]: https://flowcrypt.com/ https://flowcrypt.com/

jrochkind1 8y ago
Hmm. Solutions like signal or whatsapp also used their "own custom encryption scheme" (in that sense), instead of PGP. I'm not sure PGP is actually good enough that alternatives aren't desirable. Here's a Wired article saying "PGP is dead... use Signal for your encrypted messaging instead": https://www.wired.co.uk/article/efail-pgp-vulnerability-outlook-thunderbird-smime https://www.wired.co.uk/article/efail-pgp-vulnerability-outl... Here's respected cryptographer Matthew Green saying PGP is "a model of email encryption that’s fundamentally broken" in 2014. https://blog.cryptographyengineering.com/2014/08/13/whats-matter-with-pgp/ https://blog.cryptographyengineering.com/2014/08/13/whats-ma... I think there was another more recent "what's the matter with PGP" post I saw on HN, I found these above while trying to see if I could remember what I saw more recently.
- Leace 8y ago
  > Solutions like signal or whatsapp also used their "own custom encryption scheme" (in that sense), instead of PGP. But Signal's "own custom encryption scheme" have obvious advantages over PGP, for example forward secrecy. That's what I meant by "I can understand (...) if they have something better". In Tutanota's case judging from their public descriptions the scheme doesn't have any advantages over PGP as it is currently used. Implementing custom crypto usually ends up with something like this: https://tutanota.uservoice.com/forums/237921-general/suggestions/7858974-tutanota-is-using-unauthenticated-aes-cbc-encrypti https://tutanota.uservoice.com/forums/237921-general/suggest...

tkfu 8y ago

> While it is possible to encrypt certain emails in Gmail with GPG, Google can still read all email meta-data such as email addresses and subject lines. Better use a Gmail alternative that encrypts your entire mailbox and contacts automatically. This is nonsense. Any email service will be able to see the recipients (and senders) of your messages, because that's how email works. Subject lines too, again, because that's how email works. E2E encryption of email is a good thing, GPG is hard. These things have be true forever.

alfiedotwtf 8y ago
This. Can we please kill the idea of "safe email" forever. Email leaks like a sieve. In fact, It would be interesting to see if the Carbon Copy (CC:) feature of email violates GDPR.
- alias_neo 8y ago
  Don't even get me started on domain spoofing. I get so much junk every day due to bounce backs of people spoofing my domain to send junk. SPF, DKIM and DMARC have done (and can do) nothing to help. Email is broken, and this, sadly, is the price we pay for the federation it provides for a technology of its age.
  - simias 8y ago
    Are you sure your server is correctly configured? I host my own server on a custom domain and while I do receive a non-negligible amount of spam I don't think I've ever noticed my domain being spoofed. >SPF, DKIM and DMARC have done (and can do) nothing to help. Isn't that precisely what these technologies are supposed to help? Why do you say that they can't do anything?
    - kikoreis 8y ago
      You are right that they are designed to prevent spoofing. The problem is that the recipient server needs to be configured to use it and not all servers do, for reasons spanning false positives to ignorance. So if you have a fairly old or known domain you will get non trivial amounts of backscatter from spoofed email being sent to invalid or otherwise rejected addresses.

hannob 8y ago

I know it's a bit old, but since I read this I cannot possibly take Tutanota seriously on anything crypto: https://tutanota.uservoice.com/forums/237921-general/suggestions/7858974-tutanota-is-using-unauthenticated-aes-cbc-encrypti https://tutanota.uservoice.com/forums/237921-general/suggest... https://seclists.org/fulldisclosure/2015/Jun/58 https://seclists.org/fulldisclosure/2015/Jun/58

snvzz 8y ago

We need the Dark Mail Alliance more than ever. https://en.wikipedia.org/wiki/Dark_Mail_Alliance https://en.wikipedia.org/wiki/Dark_Mail_Alliance https://darkmail.info/downloads/dark-internet-mail-environment-june-2018.pdf https://darkmail.info/downloads/dark-internet-mail-environme... https://github.com/lavabit/ https://github.com/lavabit/

hguhghuff 8y ago

The problem with Email is that it’s routed, store and forward, whereas there’s no reason why it shouldnt be point to point. If you wanted to revolutionize email then you’d create a point to point email service.

robjan 8y ago
That shouldn't be a problem if it's properly encrypted. The whole internet is routed over various switches owned by various entities.
flurdy 8y ago
Point to point is very fragile and inflexible. There are many good reasons for email (and internet in general) was designed to be routable.
krageon 8y ago
There's a reason peer to peer isn't seen as a great idea for messaging and that reason is it's been tried many, many times and it doesn't work well. For some people it just won't work well ever. Furthermore, it doesn't mesh with the expectations most people will have of a mail service (you push the mail out and it will arrive some day regardless of what you do), which makes it a bad fit for the use-case to begin with.

mikekchar 8y ago

In the meantime I'm using mutt on the desktop on K9 on Android. I have to say that K9 is brilliant (mutt less so, but I like it ;-)). It's the closest "it just works" E2E mail client I've ever used. Unfortunately the reality of PGP is that it's hard for a normal person to use, although I've got my Dad using it for all of our email.

kjar 8y ago

Mass surveillance is kinda Google’s model

yuz 8y ago

This is a promotion article for an end-to-end encrypted mail service called tutanota. They claim that google abandonment of the mail encryption project impiles that gmail encryption will necessarily never be available for gmail users.

vlastik 8y ago

Why not something like Let's Encrypt, but for S/MIME?

rtnl 8y ago
That's actually what a Swiss startup called Vereign seems to be working on: https://medium.com/@ggreve/nobody-cares-about-signatures-a56505b8ce04 https://medium.com/@ggreve/nobody-cares-about-signatures-a56...

Causality1 8y ago

"shows where Google's real interests are: Not in protecting their users' private data, but in harvesting it for their own benefit." Well, Duh. That's the deal. "in exchange for this service we will scrape your data in order to serve ads". If you don't like it go somewhere else. Google doesn't owe you a free email service.

rdxm 8y ago

OK, did anyone ever honestly think this would happen? 'Cause if they did that was pretty naive...

chiefalchemist 8y ago

I'm not a fan of email, and not only because of security / privacy. Yes, it's ubiquitous and convenient; and great for quick simple messages. But it's not (in a biz / life context) a project management tool. So aside from "where do you want to go for lunch?" the appropriateness of email breaks down pretty quick. Unfortunately, the habit and convenience not so much so. Ideally, we're nudging towards a tipping point where email gets replaced by more appropriate (planning and proj management) tools - even at the personal level.

arbitrage 8y ago
I'm not a fan of cars, because they don't perform well in lakes. I'm hoping we're moving toward a world where we use different tools for different tasks. Something engineered to float would be much better, in my opinion.
- chiefalchemist 8y ago
  Yes! Thank you for proving my point[1]!! That is, at this point email is the internet equivalent of a fax machine. It's a hammer (or car) that most are using as a screwdriver (or boat). Factor in the lack of security / privacy and email should be marginalized, just as the fax machine was. [1] Yes, I realize it was not your intent. But the fact is, your analogy is a good one for the point I'm trying to make.

stirfrykitty 8y ago

If all one wants to do is communicate securely with another person and what your typing is private but not "illegal", then why even send email. Simply use the Drafts in GMail. Compose an email and leave it in Drafts. Each person amends the draft and they can agree on times to check and update. This has been done with great success before if you want nothing "going across the wire" so to speak.

LinuxBender 8y ago

GPG is hard for some, but 7-zip is easy for most. Not perfect, but perfect is enemy of good. Just put your email, files, whatever in a 7-zip encrypted and compressed file and email that. Tell your friend the password over voice chat, or some other chat that is in no way related to your mail provider. Even a weak password is better than trusting the mail provider to handle this job. Here is a 7-zip file with a very simple password. [1] Please reply with the contents of the text file in the 7z. [1] - https://tinyvpn.org/5/e/f/5efed61e6efe235d965547999292279e.7z https://tinyvpn.org/5/e/f/5efed61e6efe235d965547999292279e.7...

jimnutt 8y ago

So, I'm sure this idea has holes all over it, but how about a very simple service that you log into with your PGP public key, then would allow you to post encrypted messages to other PGP public keys and retrieve messages posted to your public key. It could be fully anonymous, depending on your choice of keys. It would be very similar to the mixmaster remailers, except it wouldn't actual mail anything as it wouldn't have any identifiable information other than the public key.

dredmorbius 8y ago
PGP itself leaks a huge amount of metadata. A known problem on open mailing lists and Usenet.