5 ms·

A plea to Google: Protect our e-mail privacy

23 points by iProject 14y ago

napoleond 14y ago
My little company has started working on a solution to this: http://parley.co http://parley.co Google will never store email in a properly encrypted fashion, because their incentives lie with advertisers rather than with users. The only way for encrypted email to both work and reach mass appeal is for it to be implemented in such a way that private keys never touch the server while still being ridiculously simple to use at a highly accessible price point.
- duaneb 14y ago
  > Google will never store email in a properly encrypted fashion, because their incentives lie with advertisers rather than with users. Also I'm pretty sure search would suck with encryption, which is easily the primary draw of GMail for many people.
  - napoleond 14y ago
    I agree that search is pretty nice to have, but most of the time I find myself searching for "messages from so-and-so" or "that email I wrote about X" which is still searchable after encryption (subject fields remain unencrypted, and you obviously also have to/from/date/time). For deeper searches, a client could decrypt and search a smaller time span (messages to X last week containing Y). It's still a trade-off, but I don't think it's a deal-breaker at all. I also think we overestimate how much non-geeks know about search features in GMail.
    - thezilch 14y ago
      Why are those fields still searchable after encryption? Doesn't that fly in the face of the article's utopian state of email? I can still see you're emailing with this contact, at this frequency, and with these subjects; seems like an awful lot of insecure leakage.
      - napoleond 14y ago
        PGP doesn't encrypt the recipient's address for obvious reasons. Subject and sender are useful for the recipient; it's a tradeoff, as all security is.
    - duaneb 14y ago
      Most of my searches are for content, unfortunately. I'm sure I could retrain myself for some of the queries to operate solely on metadata/subject, but not all of them. However, it's not like we can't do this now, at least for outgoing mail. PGP encryption works as well with gmail as it does with other encryptions, and you could just delete any non-encrypted incoming email. On a personal note, there's really nothing in my email that I feel a need to encrypt- at worst, someone might find eight digits of a credit card, or an old password, or an embarrassing email to an old girlfriend. Certainly nothing that would scare me out of the immense convenience of allowing GMail my unencrypted email.
      - napoleond 14y ago
        You have a really valid point, and I appreciate the feedback. (If we're way off the mark for how many people would use this, that's obviously a good thing to know.) PGP encryption can indeed work with any mail service but it's way too cumbersome for the average person, and "deleting any non-encrypted incoming email" wouldn't really be sufficient--to my knowledge there's no public data on the amount of time between Google flagging an item as being deleted and the time where it actually disappears from all disks but due to backups, etc, I would expect it to be a really long time. Either way, for external (non-gmail) messages unless both parties are using PGP the whole exchange can easily be intercepted at any point along the way (users are connected to gmail over SSL but external email servers typically aren't). Many people send sensitive information over email without any hesitation (eg. it's probably the most commonly used method for exchanging passwords) and the amount of ways your benign emails could be used against you (in court or otherwise) is probably scarier than you think. You don't need to be plotting a violent overthrow of the government for your words to be used against you. EDIT: FWIW, it's really hard to talk about this stuff without sounding like the guy on the street corner with a placard. I don't think a rogue employee at Google is going to destroy your life, nor do I expect the thought police to someday arrest you based on your email history. I do believe that we have a legitimate right to privacy in our communications which just isn't being met today, and I think that if more people were aware of the current reality they would agree. Protecting our data is ultimately our own responsibility, and I think there are better options for "normal" people than what's currently out there.
  - dredmorbius 14y ago
    Search would have to rely on a local storage option. More reason why email as a service on a centralized server shared by multiple interests without assured user security zones independent of the server has fundamental limitations.
jmillikin 14y ago
(disclaimer: I'm employed by Google, though not in anything related to Gmail) The article quotes Vint Cerf as saying that encryption isn't being used because it would inhibit advertising, but I think that's incorrect. There is no obvious reason why ads couldn't be selected client-side, with the text of a message sent to Google over an encrypted connection and not stored. In my opinion, there are at least three much more significant reasons why Gmail won't support end-to-end encryption: 1) It puts a huge barrier in front of new users. Instead of picking a username and password, now they have to create an encryption key, have a (strong!) password for the key, install client-side software to manage it, keep a backup of the key, and keep backups of their email in an encrypted form (with yet another strong password). Can you imagine any ordinary person going through with all that just to read email? -- 2) User-managed encryption would be a support nightmare. Imagine: your grandmother buys a new laptop, and donates her old beige box to a local school. After getting home, she tries to check her email. Except she can't, because the encryption keys were on her old computer, and now they're just noise on some platters because the school's IT guy wiped the drive. Would you want to be the customer support agent who had to tell her that her email was gone forever, and that she would have to make a new account with a new address? This is why no major company encourages users to manage their own encryption keys, and why every company that does will never become a major company. -- 3) Google's primary value-add to anything is search. That's their brand, they are the company people go to for finding stuff. End-to-end encryption means that Gmail can't do search any more, and then what's the point of even having Gmail? Even if you could somehow convince users that it's worth putting up with all the extra hassle to protect their email, you'll never convince a company that it should scrap one of its most successful products just because a fraction of a percent of its userbase thinks its existing security features are insufficient. ------------------------ Here's another thought. The world the author describes, where people install special client software to manage their keys and read their email, ALREADY EXISTS. If people actually want to, they can download Thunderbird and GPG and set up their keys and treat Gmail as just another IMAP/SMTP service. It's an annoying process, but the only ways to make it simpler would also render it useless by reducing the security. So really the author isn't asking for Gmail to support encrypted email, he's asking Gmail to stop supporting un-encrypted email. Hands up if you think this will ever happen. The fact that nobody outside the crypto-nerd community uses existing client-side encryption support is strong evidence that most users consider the convenience of provider-readable mail to be more important than protection against police warrants.
jackpirate 14y ago
GMail will probably never encrypt our emails for us. But what it could do is automatically decrypt someone else's email and verify the signature. This would make encryption much more accessible without any (advertising) cost to Google.
- jmillikin 14y ago
  Automatic decryption would require uploading a copy of the recipient's private key to Gmail, which rather defeats the purpose of end-to-end encryption. For protecting mail in transit, SMTP TLS is just as secure and much easier to deploy.
  - AnthonyMouse 14y ago
    SMTP TLS has to be deployed by the email server admin. Google could implement PGP (with the private key stored on their server) and it would work with any PGP-compatible email client regardless of support by the peer's email server. So for example, if your company runs your email server and doesn't use SMTP TLS, you can still use e.g. Thunderbird with GPG and correspond with someone who uses gmail without the gmail user having to take any steps whatsoever -- it would be trivial for google to supply a page like 'https://gmail.com/[username@gmail.com]/PGP https://gmail.com/[username@gmail.com]/PGP (and autogenerate a new key for any guessed address to thwart spammers guessing addresses), where you could get a copy of the user's public key and then send encrypted messages without the gmail user having to do a single thing. That doesn't keep the email private from Google, but if your only concern is to keep your communications private from your email provider for some reason (or from your ISP etc. if you like your email provider other than the fact that they don't use SMTP TLS), it gives you something you didn't have before.
    - jmillikin 14y ago
      "That doesn't keep the email private from Google, but if your only concern is to keep your communications private from your email provider" If you use Gmail, then Google is your email provider.
graue 14y ago
Someone needs to invent a Firefox or Chrome addon that solves this problem. Here's how I see it working. You get a message on Gmail, and it looks like this: This message is encrypted with FooAddon. To view it, copy and paste the encrypted message to a FooAddon tab. ----FOOADDON MESSAGE START ...a bunch of base64-encoded binary data... ----FOOADDON MESSAGE END You paste that into the addon's tab and it uses your private key to decrypt and show the message. To send, you select the recipient's public key in a FooAddon tab and type your message there, then click Encrypt. It gives you something like the above which you then copy and paste back into Gmail. Clumsy, yes, but you'd have a working proof-of-concept that would allow you to send and receive encrypted messages through any website with a text field without leaving the browser. The security implications of being able to type a secure message directly in Gmail and be sure Google isn't reading it with JavaScript are no doubt much more complicated.
- jmillikin 14y ago
  http://www.mozilla.org/en-US/thunderbird/ http://www.mozilla.org/en-US/thunderbird/ https://addons.mozilla.org/en-us/thunderbird/addon/enigmail/ https://addons.mozilla.org/en-us/thunderbird/addon/enigmail/
  - graue 14y ago
    Since you missed it, the key point of my proposal was that it works: > through any website with a text field > without leaving the browser
    - jmillikin 14y ago
      I don't consider either of those to be useful, because once you've had to open a new window/tab, you might as well just have opened another application. This recent obsession with rewriting the world to run in a jumped-up document rendering system is unhealthy and insane.
      - graue 14y ago
woodchuck64 14y ago
Don't quite understand why Google drafts would be thought safer than Google email (between Google addresses). Aren't both sent via (technically unsafe) https and stored on some google disk somewhere?
- pavel_lishin 14y ago
  If I send you an e-mail, it exists in at least two places on Google's servers, and on whatever devices you've used to read and send the message.
  - woodchuck64 14y ago
    I agree that it exists on two places on Google's servers, but a draft also exists on every device that has used that account (and viewed or edited the draft).

23 points by iProject 14y ago

My little company has started working on a solution to this: http://parley.co http://parley.co Google will never store email in a properly encrypted fashion, because their incentives lie with advertisers rather than with users. The only way for encrypted email to both work and reach mass appeal is for it to be implemented in such a way that private keys never touch the server while still being ridiculously simple to use at a highly accessible price point.

duaneb 14y ago
> Google will never store email in a properly encrypted fashion, because their incentives lie with advertisers rather than with users. Also I'm pretty sure search would suck with encryption, which is easily the primary draw of GMail for many people.
- napoleond 14y ago
  I agree that search is pretty nice to have, but most of the time I find myself searching for "messages from so-and-so" or "that email I wrote about X" which is still searchable after encryption (subject fields remain unencrypted, and you obviously also have to/from/date/time). For deeper searches, a client could decrypt and search a smaller time span (messages to X last week containing Y). It's still a trade-off, but I don't think it's a deal-breaker at all. I also think we overestimate how much non-geeks know about search features in GMail.
  - thezilch 14y ago
    Why are those fields still searchable after encryption? Doesn't that fly in the face of the article's utopian state of email? I can still see you're emailing with this contact, at this frequency, and with these subjects; seems like an awful lot of insecure leakage.
    - napoleond 14y ago
      PGP doesn't encrypt the recipient's address for obvious reasons. Subject and sender are useful for the recipient; it's a tradeoff, as all security is.
  - duaneb 14y ago
    Most of my searches are for content, unfortunately. I'm sure I could retrain myself for some of the queries to operate solely on metadata/subject, but not all of them. However, it's not like we can't do this now, at least for outgoing mail. PGP encryption works as well with gmail as it does with other encryptions, and you could just delete any non-encrypted incoming email. On a personal note, there's really nothing in my email that I feel a need to encrypt- at worst, someone might find eight digits of a credit card, or an old password, or an embarrassing email to an old girlfriend. Certainly nothing that would scare me out of the immense convenience of allowing GMail my unencrypted email.
    - napoleond 14y ago
      You have a really valid point, and I appreciate the feedback. (If we're way off the mark for how many people would use this, that's obviously a good thing to know.) PGP encryption can indeed work with any mail service but it's way too cumbersome for the average person, and "deleting any non-encrypted incoming email" wouldn't really be sufficient--to my knowledge there's no public data on the amount of time between Google flagging an item as being deleted and the time where it actually disappears from all disks but due to backups, etc, I would expect it to be a really long time. Either way, for external (non-gmail) messages unless both parties are using PGP the whole exchange can easily be intercepted at any point along the way (users are connected to gmail over SSL but external email servers typically aren't). Many people send sensitive information over email without any hesitation (eg. it's probably the most commonly used method for exchanging passwords) and the amount of ways your benign emails could be used against you (in court or otherwise) is probably scarier than you think. You don't need to be plotting a violent overthrow of the government for your words to be used against you. EDIT: FWIW, it's really hard to talk about this stuff without sounding like the guy on the street corner with a placard. I don't think a rogue employee at Google is going to destroy your life, nor do I expect the thought police to someday arrest you based on your email history. I do believe that we have a legitimate right to privacy in our communications which just isn't being met today, and I think that if more people were aware of the current reality they would agree. Protecting our data is ultimately our own responsibility, and I think there are better options for "normal" people than what's currently out there.
- dredmorbius 14y ago
  Search would have to rely on a local storage option. More reason why email as a service on a centralized server shared by multiple interests without assured user security zones independent of the server has fundamental limitations.

jmillikin 14y ago

(disclaimer: I'm employed by Google, though not in anything related to Gmail) The article quotes Vint Cerf as saying that encryption isn't being used because it would inhibit advertising, but I think that's incorrect. There is no obvious reason why ads couldn't be selected client-side, with the text of a message sent to Google over an encrypted connection and not stored. In my opinion, there are at least three much more significant reasons why Gmail won't support end-to-end encryption: 1) It puts a huge barrier in front of new users. Instead of picking a username and password, now they have to create an encryption key, have a (strong!) password for the key, install client-side software to manage it, keep a backup of the key, and keep backups of their email in an encrypted form (with yet another strong password). Can you imagine any ordinary person going through with all that just to read email? -- 2) User-managed encryption would be a support nightmare. Imagine: your grandmother buys a new laptop, and donates her old beige box to a local school. After getting home, she tries to check her email. Except she can't, because the encryption keys were on her old computer, and now they're just noise on some platters because the school's IT guy wiped the drive. Would you want to be the customer support agent who had to tell her that her email was gone forever, and that she would have to make a new account with a new address? This is why no major company encourages users to manage their own encryption keys, and why every company that does will never become a major company. -- 3) Google's primary value-add to anything is search. That's their brand, they are the company people go to for finding stuff. End-to-end encryption means that Gmail can't do search any more, and then what's the point of even having Gmail? Even if you could somehow convince users that it's worth putting up with all the extra hassle to protect their email, you'll never convince a company that it should scrap one of its most successful products just because a fraction of a percent of its userbase thinks its existing security features are insufficient. ------------------------ Here's another thought. The world the author describes, where people install special client software to manage their keys and read their email, ALREADY EXISTS. If people actually want to, they can download Thunderbird and GPG and set up their keys and treat Gmail as just another IMAP/SMTP service. It's an annoying process, but the only ways to make it simpler would also render it useless by reducing the security. So really the author isn't asking for Gmail to support encrypted email, he's asking Gmail to stop supporting un-encrypted email. Hands up if you think this will ever happen. The fact that nobody outside the crypto-nerd community uses existing client-side encryption support is strong evidence that most users consider the convenience of provider-readable mail to be more important than protection against police warrants.

jackpirate 14y ago

GMail will probably never encrypt our emails for us. But what it could do is automatically decrypt someone else's email and verify the signature. This would make encryption much more accessible without any (advertising) cost to Google.

jmillikin 14y ago
Automatic decryption would require uploading a copy of the recipient's private key to Gmail, which rather defeats the purpose of end-to-end encryption. For protecting mail in transit, SMTP TLS is just as secure and much easier to deploy.
- AnthonyMouse 14y ago
  SMTP TLS has to be deployed by the email server admin. Google could implement PGP (with the private key stored on their server) and it would work with any PGP-compatible email client regardless of support by the peer's email server. So for example, if your company runs your email server and doesn't use SMTP TLS, you can still use e.g. Thunderbird with GPG and correspond with someone who uses gmail without the gmail user having to take any steps whatsoever -- it would be trivial for google to supply a page like 'https://gmail.com/[username@gmail.com]/PGP https://gmail.com/[username@gmail.com]/PGP (and autogenerate a new key for any guessed address to thwart spammers guessing addresses), where you could get a copy of the user's public key and then send encrypted messages without the gmail user having to do a single thing. That doesn't keep the email private from Google, but if your only concern is to keep your communications private from your email provider for some reason (or from your ISP etc. if you like your email provider other than the fact that they don't use SMTP TLS), it gives you something you didn't have before.
  - jmillikin 14y ago
    "That doesn't keep the email private from Google, but if your only concern is to keep your communications private from your email provider" If you use Gmail, then Google is your email provider.

graue 14y ago

Someone needs to invent a Firefox or Chrome addon that solves this problem. Here's how I see it working. You get a message on Gmail, and it looks like this: This message is encrypted with FooAddon. To view it, copy and paste the encrypted message to a FooAddon tab. ----FOOADDON MESSAGE START ...a bunch of base64-encoded binary data... ----FOOADDON MESSAGE END You paste that into the addon's tab and it uses your private key to decrypt and show the message. To send, you select the recipient's public key in a FooAddon tab and type your message there, then click Encrypt. It gives you something like the above which you then copy and paste back into Gmail. Clumsy, yes, but you'd have a working proof-of-concept that would allow you to send and receive encrypted messages through any website with a text field without leaving the browser. The security implications of being able to type a secure message directly in Gmail and be sure Google isn't reading it with JavaScript are no doubt much more complicated.

jmillikin 14y ago
http://www.mozilla.org/en-US/thunderbird/ http://www.mozilla.org/en-US/thunderbird/ https://addons.mozilla.org/en-us/thunderbird/addon/enigmail/ https://addons.mozilla.org/en-us/thunderbird/addon/enigmail/
- graue 14y ago
  Since you missed it, the key point of my proposal was that it works: > through any website with a text field > without leaving the browser
  - jmillikin 14y ago
    I don't consider either of those to be useful, because once you've had to open a new window/tab, you might as well just have opened another application. This recent obsession with rewriting the world to run in a jumped-up document rendering system is unhealthy and insane.
    - graue 14y ago

woodchuck64 14y ago

Don't quite understand why Google drafts would be thought safer than Google email (between Google addresses). Aren't both sent via (technically unsafe) https and stored on some google disk somewhere?

pavel_lishin 14y ago
If I send you an e-mail, it exists in at least two places on Google's servers, and on whatever devices you've used to read and send the message.
- woodchuck64 14y ago
  I agree that it exists on two places on Google's servers, but a draft also exists on every device that has used that account (and viewed or edited the draft).