7 ms·

Gmail E2E is as terrible as expected

186 points by HypnoticOcelot 1y ago

cmdhaus 1y ago
[dead]
ranger_danger 1y ago
I think one of the growing threats lately in the community has been over malicious client-side javascript, especially when the client handles end-to-end encrypted content (used on sites like Proton, MEGA etc.), so requiring users to trust Google with the contents of these client pages, and by extension the emails themselves, seems (in my opinion) to defeat the entire point of this feature. Some work in this area has been done in the form of browser extensions that are used to verify signed assets delivered to the client: https://github.com/freedomofpress/webcat https://github.com/freedomofpress/webcat https://github.com/tasn/webext-signed-pages https://github.com/tasn/webext-signed-pages https://github.com/jahed/webverify https://github.com/jahed/webverify https://github.com/facebookincubator/meta-code-verify https://github.com/facebookincubator/meta-code-verify But unfortunately for now, none of these are seeing wide adoption and this remains an unsolved issue. It also does not require anyone to use known-good, audited and verified open-source components, meaning even if the client code is signed, it can still be malicious... there must be a greater reason to trust the code than just "trust me bro".
486sx33 1y ago
[flagged]
kardianos 1y ago
This is how all HIPAA "secure email" works. Outlook, Zoho, clinic comms, BECAUSE it lets you revoke email access. If you want an opportunity in this space, it isn't actually encrypted emails, but possibly standardizing and streamlining such "message pointers" and address endpoint verification.
- perching_aix 1y ago
  > lets you revoke (...) access That's pretty funny.
zer0zzz 1y ago
Doesn’t proton mail also do this for sending encrypted mail to folks with no encryption? They ought to do pgp though
- jitl 1y ago
  Can’t expect a civilian to manage pgp keys or go to key signing parties
  - XorNot 1y ago
    The anti-establishment fervor of open source crypto developers is the reason this is a problem though. Most people, for most things, don't need to verify trust outside of normal government channels. i.e. any business I correspond with, trust is via the government that they are a business bound by the relevant legal system I live in. Same story with communicating with basically anyone: if their GPG key was signed by the common government key, then hey, good enough for anyone. The problem is...we don't have the infrastructure for any of this. And GPG key servers are inadequate for maintaining suitable privacy for people if they were used at this scale. But we certainly could provide the means by existing technologies: e.g. nothing stops us making drivers licenses and other forms of ID smart cards.
    - solardev 1y ago
      It depends a lot on the government in question too. In the US very few people would trust the government to handle something like this. The certificate authority system is run by big tech companies and nonprofits, for example, not the government. Trusting the government as a peer makes sense for government sites, but for anything else, it just makes censorship way too easy. Even among businesses, we normally trust the middleman (the credit card issuer, and their protections and chargebacks) over the government. If a business screws over a regular consumer, the government isn't really going to do anything. Maybe you have a more civilized society and functional government where you live. We don't.
      - XorNot 1y ago
solardev 1y ago
Isn't this how banks send secure messages too? You can't send secure emails to arbitrary clients otherwise. PGP stands no chance of being adopted by regular users.
Freak_NL 1y ago
This was already happening, unfortunately. The user's mail agent is deemed untrustworthy (and so is the user), so every service which needs to send confidential data just turns your email into a notification with a link. There are so many of these, but often they are limited in scope. For sectors like healthcare you have companies offering this type of service to companies which need to adhere to security theatre standards such as ISO 27001, and because nations often have their own added requirements for specific sectors (think HIPAA in the US or NEN 7510 in the Netherlands) these services tend to remain focussed on single countries. Then there are the national governments and things like insurance companies. All happily sending message notifications where you need to sign in to their own portals. Securing email is too complex, so everyone builds their own secured portal thingy, and your mailbox has become a receptacle for notifications. Figuring out a solution would require cooperation, pragmatic lawmaking, and giving up those nice cashcows of moated portals, so it won't happen.
- modeless 1y ago
  I hate this so much. I will pay for a service that takes all these content-free messages and goes to the website and logs in and extracts the actual message content and puts it in my inbox. Anyone want to make that? I actually think there is a more general opportunity here with AI. Every app and website and UI I use is optimized by a gaggle of PMs to achieve business objectives that don't necessarily benefit me. AI is getting to the point where soon it will be able to use these non-aligned UIs for me, and present to me a much simpler UI customized just for me, that does what I actually want and no more.
  - jack0813 1y ago
    You can probably do this fairly easily already, like this: - Fetch your emails using any of the common local mail sync tools - Some processing to clean up the plaintext version, may not be necessary even - Send it to an LLM to extract a link - Open up a headless browser, trigger something like SingleFile to extract its content. Though you'll have to keep the cookie refreshed, but if it is initially logged in, this should be fine since you can also program something to keep refreshing every once in a while.
stwrzn 1y ago
What happens if the sender's Google account ceases to exist for whatever reason? What if Google ceases to exist? I know that there are a lot of HIPAA "secure email" solutions that also do this, but I don't want this to become more common practice then it already is...
- toomuchtodo 1y ago
  Keep HARs from the browser if you need your own record of the messages. Next step would be to determine how to extract the messages from a history of HARs and inject into your own mailbox or other storage system for archiving and search. Perhaps a browser extension to automate this automated logging of message retrieval.
- solardev 1y ago
  IMO those are different use cases. If that sender or Google itself were to disappear, hopefully the messages would just disappear too. It's better that they become inaccessible rather than public. Long term archival is a different use case altogether, especially of encrypted materials. It's questionable whether any provider or medium can survive over the long term, so it's better to use an encryption system where you hold the keys and the encrypted data can be migrated to any sort of storage or provider over the years.
- TJSomething 1y ago
  I just keep all my Gmail synced into local Thunderbird via IMAP.
  - weikju 1y ago
    Doesn’t matter. If using this and I send you an email, and my account disappears, you can no longer read the email you received because it’s merely a link to read something from my account on Google.
- philistine 1y ago
  Coming to Google's Blog in 2028: Focusing on the Future of Secure Communication [...] Starting next week, E2E emails on Gmail will no longer function, and all your E2E messages on Gmail will be deleted on February 1 2029.
n3storm 1y ago
I guess minimal gmail for e2e is the tariff we have to pay for privacy and freedom. wink.
otterley 1y ago
> I'm not going into how much this is not E2E, as this has already been proven By whom? It looks like E2E to me. It’s just that both ends are controlled by the same entity.
p2detar 1y ago
The E2E problem has already been solved long time ago. We used to have Thunderbird with an OpenPGP extension and GPG keys. Then there were a whole plethora of products were build around Lotus Notes Domino that provided a central place for securing outgoing E-mail using either S/MIME or GPG keys. All of this on premises. Then came the Cloud and obliterated these products. And for what? edit: typos
- bigfatkitten 1y ago
  > The E2E problem has already been solved long time ago. We used to have Thunderbird with an OpenPGP extension and GPG keys. It was never really solved, PGP email is a usability disaster. Client support (especially on mobile) is limited. Headers, including the subject line remain in cleartext. Users forget to click the "encrypt email" button and so messages go out in the clear; sometimes in reply, and so the entire conversation is exposed. Key exchange with new recipients is tedious to do securely. Not to mention the extra issues caused by HTML in message bodies. https://www.eff.org/deeplinks/2018/05/not-so-pretty-what-you-need-know-about-e-fail-and-pgp-flaw-0 https://www.eff.org/deeplinks/2018/05/not-so-pretty-what-you...
  - AshamedCaptain 1y ago
    Ah, the usual "A is an unpopular standard, so we decided to do our own proprietary thing". Guess what: for it become popular, it actually has to be implemented. If Google implemented it in Gmail, many of these purported issues would go away . It would still not truly be E2EE mail, but then again neither is this monstrosity.
  - aborsy 1y ago
    It’s a disaster because email providers don’t want to offer E2EE or make it easy. Is it that hard to generate a certificate for each email address client side and store that, and the private key encrypted with the user’s password, on the provider’s server? The majority of email is gmail and Google could make that E2EE by default. Countless products that have successfully implemented public key distribution (proton mail, instant messaging, …).
tptacek 1y ago
This is how most commercial secure email products work.
fnord77 1y ago
how else are they going to push ads?
jonathantf2 1y ago
This is exactly how M365's solution works. Decrypts if the recipient is using MSN or EXO, otherwise punt them to a webpage.
jurschreuder 1y ago
People in China could not open a url sent in Gmail. I happened to be in China, I tried to open the webpage and it worked, no firewall. I hovered on the link in Gmail and Chrome told me left bottom it was just that exact url. But when I opened the url it got blocked by the great firewall. Why? Any link in Gmail secretly gets replaced by a link to Google that tracks you and then redirects you to the original link. The most obnoxious thing about this I think is that Chrome shows the original link.
- josephg 1y ago
  That’s a classic technique to track click through rates. Google.com has done this forever. The technique is to make an actual link in HTML (<a href=…>) then add an event handler which cancels the link’s default behaviour when you click it - and replaces it with javascript, or a tracking link. I understand why Google.com wants that data. But in an email client it’s extremely obnoxious.
  - SparkyMcUnicorn 1y ago
    I thought Gmail didn't support js execution. Did Google make an exception for themselves?
    - fn-mote 1y ago
      It’s not JS in the message. It’s the JS of the GMail page.
  - ChadNauseam 1y ago
    If it’s replaced with a tracking link, I think it might be just as effective to use the `ping` property on browsers that support it
    - josephg 1y ago
      Huh - I didn't know that existed. Its not supported in firefox or IE11 though - and probably will never be. (IE11 probably isn't super relevant now - but it was almost certainly more relevant when that tracking code was written. You could use feature detection - but its much easier to just use their hacky javascript everywhere instead.) https://developer.mozilla.org/en-US/docs/Web/API/HTMLAnchorElement/ping https://developer.mozilla.org/en-US/docs/Web/API/HTMLAnchorE... https://caniuse.com/ping https://caniuse.com/ping
tky 1y ago
All the takes on this release miss one crucial point: if you want people to adopt E2E encryption, you must reduce friction. For users of Gmail, that means familiar elements and flow to their usual use of Gmail. If this lets even a handful of people use more secure messaging, it’s a win. For Google workspace-centric orgs it’s a good step in the right direction. If you disagree, go set up GPG on a non-tech’s computer, tell them they need to use Thunderbird or some other helper app(s), and see if you can even go home before being asked to remove it all.
- weikju 1y ago
  Like so many security gestures from Big Tech, it’s a win wrapped in a curse (or lock-in, tracking, what have you depending on the solution. )
commandersaki 1y ago
How does the E2EE happen if you're clicking a gmail link? One thought is the secret bit is tacked onto the anchor part of the URL, but the secret is in plaintext both on the senders sent email and on the recipient side.
Woodi 1y ago
email is dead, even gov's use chat clients with emoticons ;) That email is your internet id and majority countries digital id too ? Who cares, things usually need to be so broken that even elected officials families report problems :) Then we can have some "plans" announced. EU is especially good at this - announcing (and pushing for more centralization no matter what is happening) and not fixing anything, eg. sane CPU's, when ? Rhetoric question because not in this decade...

[dead]

I think one of the growing threats lately in the community has been over malicious client-side javascript, especially when the client handles end-to-end encrypted content (used on sites like Proton, MEGA etc.), so requiring users to trust Google with the contents of these client pages, and by extension the emails themselves, seems (in my opinion) to defeat the entire point of this feature. Some work in this area has been done in the form of browser extensions that are used to verify signed assets delivered to the client: https://github.com/freedomofpress/webcat https://github.com/freedomofpress/webcat https://github.com/tasn/webext-signed-pages https://github.com/tasn/webext-signed-pages https://github.com/jahed/webverify https://github.com/jahed/webverify https://github.com/facebookincubator/meta-code-verify https://github.com/facebookincubator/meta-code-verify But unfortunately for now, none of these are seeing wide adoption and this remains an unsolved issue. It also does not require anyone to use known-good, audited and verified open-source components, meaning even if the client code is signed, it can still be malicious... there must be a greater reason to trust the code than just "trust me bro".

486sx33 1y ago

[flagged]

kardianos 1y ago

This is how all HIPAA "secure email" works. Outlook, Zoho, clinic comms, BECAUSE it lets you revoke email access. If you want an opportunity in this space, it isn't actually encrypted emails, but possibly standardizing and streamlining such "message pointers" and address endpoint verification.

perching_aix 1y ago
> lets you revoke (...) access That's pretty funny.

zer0zzz 1y ago

Doesn’t proton mail also do this for sending encrypted mail to folks with no encryption? They ought to do pgp though

jitl 1y ago
Can’t expect a civilian to manage pgp keys or go to key signing parties
- XorNot 1y ago
  The anti-establishment fervor of open source crypto developers is the reason this is a problem though. Most people, for most things, don't need to verify trust outside of normal government channels. i.e. any business I correspond with, trust is via the government that they are a business bound by the relevant legal system I live in. Same story with communicating with basically anyone: if their GPG key was signed by the common government key, then hey, good enough for anyone. The problem is...we don't have the infrastructure for any of this. And GPG key servers are inadequate for maintaining suitable privacy for people if they were used at this scale. But we certainly could provide the means by existing technologies: e.g. nothing stops us making drivers licenses and other forms of ID smart cards.
  - solardev 1y ago
    It depends a lot on the government in question too. In the US very few people would trust the government to handle something like this. The certificate authority system is run by big tech companies and nonprofits, for example, not the government. Trusting the government as a peer makes sense for government sites, but for anything else, it just makes censorship way too easy. Even among businesses, we normally trust the middleman (the credit card issuer, and their protections and chargebacks) over the government. If a business screws over a regular consumer, the government isn't really going to do anything. Maybe you have a more civilized society and functional government where you live. We don't.
    - XorNot 1y ago

solardev 1y ago

Isn't this how banks send secure messages too? You can't send secure emails to arbitrary clients otherwise. PGP stands no chance of being adopted by regular users.

Freak_NL 1y ago

This was already happening, unfortunately. The user's mail agent is deemed untrustworthy (and so is the user), so every service which needs to send confidential data just turns your email into a notification with a link. There are so many of these, but often they are limited in scope. For sectors like healthcare you have companies offering this type of service to companies which need to adhere to security theatre standards such as ISO 27001, and because nations often have their own added requirements for specific sectors (think HIPAA in the US or NEN 7510 in the Netherlands) these services tend to remain focussed on single countries. Then there are the national governments and things like insurance companies. All happily sending message notifications where you need to sign in to their own portals. Securing email is too complex, so everyone builds their own secured portal thingy, and your mailbox has become a receptacle for notifications. Figuring out a solution would require cooperation, pragmatic lawmaking, and giving up those nice cashcows of moated portals, so it won't happen.

modeless 1y ago
I hate this so much. I will pay for a service that takes all these content-free messages and goes to the website and logs in and extracts the actual message content and puts it in my inbox. Anyone want to make that? I actually think there is a more general opportunity here with AI. Every app and website and UI I use is optimized by a gaggle of PMs to achieve business objectives that don't necessarily benefit me. AI is getting to the point where soon it will be able to use these non-aligned UIs for me, and present to me a much simpler UI customized just for me, that does what I actually want and no more.
- jack0813 1y ago
  You can probably do this fairly easily already, like this: - Fetch your emails using any of the common local mail sync tools - Some processing to clean up the plaintext version, may not be necessary even - Send it to an LLM to extract a link - Open up a headless browser, trigger something like SingleFile to extract its content. Though you'll have to keep the cookie refreshed, but if it is initially logged in, this should be fine since you can also program something to keep refreshing every once in a while.

stwrzn 1y ago

What happens if the sender's Google account ceases to exist for whatever reason? What if Google ceases to exist? I know that there are a lot of HIPAA "secure email" solutions that also do this, but I don't want this to become more common practice then it already is...

toomuchtodo 1y ago
Keep HARs from the browser if you need your own record of the messages. Next step would be to determine how to extract the messages from a history of HARs and inject into your own mailbox or other storage system for archiving and search. Perhaps a browser extension to automate this automated logging of message retrieval.
solardev 1y ago
IMO those are different use cases. If that sender or Google itself were to disappear, hopefully the messages would just disappear too. It's better that they become inaccessible rather than public. Long term archival is a different use case altogether, especially of encrypted materials. It's questionable whether any provider or medium can survive over the long term, so it's better to use an encryption system where you hold the keys and the encrypted data can be migrated to any sort of storage or provider over the years.
TJSomething 1y ago
I just keep all my Gmail synced into local Thunderbird via IMAP.
- weikju 1y ago
  Doesn’t matter. If using this and I send you an email, and my account disappears, you can no longer read the email you received because it’s merely a link to read something from my account on Google.
philistine 1y ago
Coming to Google's Blog in 2028: Focusing on the Future of Secure Communication [...] Starting next week, E2E emails on Gmail will no longer function, and all your E2E messages on Gmail will be deleted on February 1 2029.

n3storm 1y ago

I guess minimal gmail for e2e is the tariff we have to pay for privacy and freedom. wink.

otterley 1y ago

> I'm not going into how much this is not E2E, as this has already been proven By whom? It looks like E2E to me. It’s just that both ends are controlled by the same entity.

p2detar 1y ago

The E2E problem has already been solved long time ago. We used to have Thunderbird with an OpenPGP extension and GPG keys. Then there were a whole plethora of products were build around Lotus Notes Domino that provided a central place for securing outgoing E-mail using either S/MIME or GPG keys. All of this on premises. Then came the Cloud and obliterated these products. And for what? edit: typos

bigfatkitten 1y ago
> The E2E problem has already been solved long time ago. We used to have Thunderbird with an OpenPGP extension and GPG keys. It was never really solved, PGP email is a usability disaster. Client support (especially on mobile) is limited. Headers, including the subject line remain in cleartext. Users forget to click the "encrypt email" button and so messages go out in the clear; sometimes in reply, and so the entire conversation is exposed. Key exchange with new recipients is tedious to do securely. Not to mention the extra issues caused by HTML in message bodies. https://www.eff.org/deeplinks/2018/05/not-so-pretty-what-you-need-know-about-e-fail-and-pgp-flaw-0 https://www.eff.org/deeplinks/2018/05/not-so-pretty-what-you...
- AshamedCaptain 1y ago
  Ah, the usual "A is an unpopular standard, so we decided to do our own proprietary thing". Guess what: for it become popular, it actually has to be implemented. If Google implemented it in Gmail, many of these purported issues would go away . It would still not truly be E2EE mail, but then again neither is this monstrosity.
- aborsy 1y ago
  It’s a disaster because email providers don’t want to offer E2EE or make it easy. Is it that hard to generate a certificate for each email address client side and store that, and the private key encrypted with the user’s password, on the provider’s server? The majority of email is gmail and Google could make that E2EE by default. Countless products that have successfully implemented public key distribution (proton mail, instant messaging, …).

tptacek 1y ago

This is how most commercial secure email products work.

fnord77 1y ago

how else are they going to push ads?

jonathantf2 1y ago

This is exactly how M365's solution works. Decrypts if the recipient is using MSN or EXO, otherwise punt them to a webpage.

jurschreuder 1y ago

People in China could not open a url sent in Gmail. I happened to be in China, I tried to open the webpage and it worked, no firewall. I hovered on the link in Gmail and Chrome told me left bottom it was just that exact url. But when I opened the url it got blocked by the great firewall. Why? Any link in Gmail secretly gets replaced by a link to Google that tracks you and then redirects you to the original link. The most obnoxious thing about this I think is that Chrome shows the original link.

josephg 1y ago
That’s a classic technique to track click through rates. Google.com has done this forever. The technique is to make an actual link in HTML (<a href=…>) then add an event handler which cancels the link’s default behaviour when you click it - and replaces it with javascript, or a tracking link. I understand why Google.com wants that data. But in an email client it’s extremely obnoxious.
- SparkyMcUnicorn 1y ago
  I thought Gmail didn't support js execution. Did Google make an exception for themselves?
  - fn-mote 1y ago
    It’s not JS in the message. It’s the JS of the GMail page.
- ChadNauseam 1y ago
  If it’s replaced with a tracking link, I think it might be just as effective to use the `ping` property on browsers that support it
  - josephg 1y ago
    Huh - I didn't know that existed. Its not supported in firefox or IE11 though - and probably will never be. (IE11 probably isn't super relevant now - but it was almost certainly more relevant when that tracking code was written. You could use feature detection - but its much easier to just use their hacky javascript everywhere instead.) https://developer.mozilla.org/en-US/docs/Web/API/HTMLAnchorElement/ping https://developer.mozilla.org/en-US/docs/Web/API/HTMLAnchorE... https://caniuse.com/ping https://caniuse.com/ping

tky 1y ago

All the takes on this release miss one crucial point: if you want people to adopt E2E encryption, you must reduce friction. For users of Gmail, that means familiar elements and flow to their usual use of Gmail. If this lets even a handful of people use more secure messaging, it’s a win. For Google workspace-centric orgs it’s a good step in the right direction. If you disagree, go set up GPG on a non-tech’s computer, tell them they need to use Thunderbird or some other helper app(s), and see if you can even go home before being asked to remove it all.

weikju 1y ago
Like so many security gestures from Big Tech, it’s a win wrapped in a curse (or lock-in, tracking, what have you depending on the solution. )

commandersaki 1y ago

How does the E2EE happen if you're clicking a gmail link? One thought is the secret bit is tacked onto the anchor part of the URL, but the secret is in plaintext both on the senders sent email and on the recipient side.

Woodi 1y ago

email is dead, even gov's use chat clients with emoticons ;) That email is your internet id and majority countries digital id too ? Who cares, things usually need to be so broken that even elected officials families report problems :) Then we can have some "plans" announced. EU is especially good at this - announcing (and pushing for more centralization no matter what is happening) and not fixing anything, eg. sane CPU's, when ? Rhetoric question because not in this decade...