6 ms·

How to support PGP encryption in Gmail

113 points by conorpp 11y ago

arat 11y ago
At the moment, end-to-end is NOT production ready, and will likely undergo further hardening in the coming months. Use at your own risk.
- mikefaille 11y ago
  https://www.mailvelope.com/ https://www.mailvelope.com/ still exist if you want production ready stuff.
- DrewHintz 11y ago
  I agree that it's not yet ready for general use, but what hardening do you expect to happen in the coming months? I'm one of the original end-to-end authors, but haven't worked on it recently.
  - koto1sa 11y ago
    I'm an developer on E2E team as well and can confirm that there's no 'hardening' going on. E2E is, to the best of our knowledge and we have expressed what that exactly means in our threat model: https://github.com/google/end-to-end/wiki/Threat-model https://github.com/google/end-to-end/wiki/Threat-model. E2E is under Google VRP (https://www.google.ch/about/appsecurity/reward-program/ https://www.google.ch/about/appsecurity/reward-program/), so if you're aware of any vulnerabilities, let us know. E2E extension is not production ready, but I myself am using the compiled version as it is, in my biased opinion, the most secure of existing PGP-in-the-browser extensions.
- kpcyrd 11y ago
  > end-to-end is NOT production ready This sounds wrong, given that "end-to-end encryption" as a concept is very much production ready.
  - coldpie 11y ago
    For better or worse, "End-To-End" is the specific Google Chrome extension being discussed in the article: https://github.com/google/end-to-end/ https://github.com/google/end-to-end/ Proper capitalization would help; Google choosing a less overloaded name in the first place would have helped more.
    - kpcyrd 11y ago
      Agreed. I was refering to the ambiguous name of the project. We're going to have a very hard time talking about end-to-end crypto to consumers without at least one person confusing this with googles addon. (Thanks google)
edent 11y ago
At the moment, I use the Mailvelope extension. https://www.mailvelope.com/ https://www.mailvelope.com/ Excellent in Chrome - a bit slow in Firefox.
- borski 11y ago
  Mailvelope is wonderful.
- leni536 11y ago
  There is WebPG too: https://www.webpg.org/ https://www.webpg.org/ It wraps around your existing gnupg installation.
jaaron 11y ago
The fact that you lose your draft when the window loses focus kills it for me.
tristor 11y ago
What is so terrible for people about using an email client? I find using the Gmail web interface to be frustrating because they've removed the ability to pop out the compose view into it's own window, so I can't easily reference information in another browser tab while writing an email for instance. Meanwhile, Gmail has excellent IMAP support, which lets me use Thunderbird + Enigmail to get excellent PGP support.
- arjie 11y ago
  Nothing is terrible, I suppose, but in the web client I personally enjoy the fast search, filtering, labeling, split pane smart inboxes, integration with Calendar, modal keyboard shortcuts (they aren't operative when you're typing in a text box but are active otherwise) and non-intrusive threading (conversation-view). The fact that all this is the same on my Macbook Pro, on my Arch Linux desktop, or when I reboot to Windows, without any effort on my part to synchronize settings makes this all rather excellent.
  - jagermo 11y ago
    Same here. I use at least 2 PCs as well as mobile Systems. I love to have the same data everywhere without having to sync something. That beeing said, I wouldn't mind running my own webmailer as long as it has most of the google apps/office 365 features. I'm hoping for mailpile myself even if it still takes some time.
  - TsiCClawOfLight 11y ago
    Except for the split inboxes, I have all of that in Thunderbird with lightning.
- viraptor 11y ago
  My main issue is that search and labels just don't work as well as in gmail webapp. Also, I'm sending 90% of emails from my phone anyway and I don't know of any good client that works both with gmail (with transparent caching of recent/viewed messages) and gpg.
  - 11y ago
leni536 11y ago
I tried to use gnupg but can't wrap my head around the web of trust. My main concern of WoT: What my signature of an other guy's public key actually means? My takeaway is that there is an implicit statement that you sign, but I don't really know what it is. According to the gnupg privacy handbook[1] this statement is roughly "I trust that this guy can properly sign other stuff" which is kind of recursive, but I like it. But when you validate if a message is really written buy a guy named John Doe then the trust path doesn't actually verify this. The trust path verifies that this guy who claims to be John Doe is good at signing other guy's keys. I don't care about that at this point. Of course people don't actually think of the statement written in the privacy handbook, they implicitly sign the statement "I trust that this guy can properly trust other stuff and I know that this guy's name is what he currently has as an ID.". There are several problems with this in practice: - Now you are signing two statements with one signature and you can't separate the two. Now using anonymous public keys becomes tricky as you lose one half of your statement. - Signing the id happens at the wrong place. Malory can revoke her identity than push "Barack Obama" as her new id, now she can send messages in the name of the president. Of course in practice it's hard, because you can't delete revoked ids from key servers. But at this point you trust the key servers. I thought that key servers are not trusted part of PGP. - gnupg guys advocate key signing parties: you gather at one place, bring your ID then sign each other's keys. The problem with this that you only verify half of your statement (id). The other half is tricky to verify (Can this guy properly protect his priv key? Will this guy just randomly sign everything he sees?), I think it makes more sense to trust a friend who you already know well. Of course there are trust levels and I think you should only use marginal trust at these parties, however I don't know what's the practice. - There are keys that are not tied to people, they are typically tied to software packages. Now what does it mean when someone signs such a key? Take putty as an example. Its master key is signed by several people. Each signature could mean that "this is the putty project's master key that is used to sign the binaries themselves" which can be verified by the given guy knowing the developer and that he is trustworthy (at this point PGP is misused though, the guy should have signed the developer's key instead and only the developer should sign the binary signing key, but it would make trust paths longer). It could also mean that "I trust that PuTTY is a great software and doesn't do anything nasty behind your back" which requires an entirely different verification. In the end the trust path a way too simplified projection of these statements and most likely you can't actually verify the statement that you care about. [1] https://www.gnupg.org/gph/en/manual.html#AEN282 https://www.gnupg.org/gph/en/manual.html#AEN282
viraptor 11y ago
FAQ is a bit confusing. They say there's only one keyring, but at https://github.com/google/end-to-end/wiki/Keyring https://github.com/google/end-to-end/wiki/Keyring they admit it was not a great idea and that they're splitting the responsibilities. Based on the last planned implementation (External Key Manager (GnuPG bridge, other hardware, network oracle etc..)), I hope it will "just work" with hardware keys.
- koto1sa 11y ago
  One of the developers here: Yes, the Keyring reimplementation is in progress and ends very soon. After the redesign, applications built on top of E2E library will be able to use different sources of both public and private keys (so it's easy to do integrations with GnuPG, hardware keys HKP, or e.g. Facebook). The API will be similar to what's in https://github.com/google/end-to-end/wiki/Keyring https://github.com/google/end-to-end/wiki/Keyring.
  - mikekchar 11y ago
    One thing that is currently missing from E2E (as far as I can tell having played with it a little in the last month) is any kind of web of trust. When I import a key, I can't tell if it has been signed by me or someone I trust. Is this on the radar for the UI after the Keyring reimplementation is finished? At the moment, what we've suggested at our work is that people manage keys in GPG and then only export keys into E2E if they trust them. But it would be nice be able to do those kinds of things in E2E (or at least be able to tell if a key was signed by me). BTW, thanks for working on this!
    - koto1sa 11y ago
      See https://github.com/google/end-to-end/wiki/Key-Distribution https://github.com/google/end-to-end/wiki/Key-Distribution. In short, we don't invest much into WoT.
      - timboslice 11y ago
mtgx 11y ago
Good to see that E2E has been progressing, but I still wish we had a PFS alternative to PGP. With today's hacks and the total state of surveillance in which we are in, it's a little crazy to expect people to use the same key 10+ years without it getting compromised. Even a year seems too much.
kweks 11y ago
It's worth mentioning Mailvelope ( https://www.mailvelope.com/ https://www.mailvelope.com/ ) - Free - Supported in FF / Chrome - Supports Gmail, Yahoo, Outlook and GMX I've been using it extensively for about 12 months now. It's solid, unobtrustive, and just .. works. Decryption of attachments would be nice, but it's definitely not a deal breaker.
- mikekchar 11y ago
  Signing of encrypted messages is not supported at the moment. Unfortunately that's a deal breaker for me :-( But it does look very nice.
  - kweks 11y ago
    Plain vanilla signing obviously works, and you could (and can, according to a quick check) - just paste your encrypted message back into the window and sign it (unless I grossly mis-understand signing, which I might do..)
- brightsize 11y ago
  FWIW Mailvelope also works fine with Fastmail in my experience.
chromano 11y ago
There's no way I'd share my private key with whatever extensions there are. It just doesn't feel right.
feld 11y ago
Wait, you have to install a JDK to use this chrome extension?
- lallysingh 11y ago
  No, to build the chrome extension from source.
  - feld 11y ago
    oh, thanks for clarifying.
drdaeman 11y ago
Does it use inline PGP or PGP/MIME? (On an unrelated note, I wonder if there's anything on mobile that supports PGP/MIME. K-9 Mail only knows about inline.)

113 points by conorpp 11y ago

arat 11y ago

At the moment, end-to-end is NOT production ready, and will likely undergo further hardening in the coming months. Use at your own risk.

mikefaille 11y ago
https://www.mailvelope.com/ https://www.mailvelope.com/ still exist if you want production ready stuff.
DrewHintz 11y ago
I agree that it's not yet ready for general use, but what hardening do you expect to happen in the coming months? I'm one of the original end-to-end authors, but haven't worked on it recently.
- koto1sa 11y ago
  I'm an developer on E2E team as well and can confirm that there's no 'hardening' going on. E2E is, to the best of our knowledge and we have expressed what that exactly means in our threat model: https://github.com/google/end-to-end/wiki/Threat-model https://github.com/google/end-to-end/wiki/Threat-model. E2E is under Google VRP (https://www.google.ch/about/appsecurity/reward-program/ https://www.google.ch/about/appsecurity/reward-program/), so if you're aware of any vulnerabilities, let us know. E2E extension is not production ready, but I myself am using the compiled version as it is, in my biased opinion, the most secure of existing PGP-in-the-browser extensions.
kpcyrd 11y ago
> end-to-end is NOT production ready This sounds wrong, given that "end-to-end encryption" as a concept is very much production ready.
- coldpie 11y ago
  For better or worse, "End-To-End" is the specific Google Chrome extension being discussed in the article: https://github.com/google/end-to-end/ https://github.com/google/end-to-end/ Proper capitalization would help; Google choosing a less overloaded name in the first place would have helped more.
  - kpcyrd 11y ago
    Agreed. I was refering to the ambiguous name of the project. We're going to have a very hard time talking about end-to-end crypto to consumers without at least one person confusing this with googles addon. (Thanks google)

edent 11y ago

At the moment, I use the Mailvelope extension. https://www.mailvelope.com/ https://www.mailvelope.com/ Excellent in Chrome - a bit slow in Firefox.

borski 11y ago
Mailvelope is wonderful.
leni536 11y ago
There is WebPG too: https://www.webpg.org/ https://www.webpg.org/ It wraps around your existing gnupg installation.

jaaron 11y ago

The fact that you lose your draft when the window loses focus kills it for me.

tristor 11y ago

What is so terrible for people about using an email client? I find using the Gmail web interface to be frustrating because they've removed the ability to pop out the compose view into it's own window, so I can't easily reference information in another browser tab while writing an email for instance. Meanwhile, Gmail has excellent IMAP support, which lets me use Thunderbird + Enigmail to get excellent PGP support.

arjie 11y ago
Nothing is terrible, I suppose, but in the web client I personally enjoy the fast search, filtering, labeling, split pane smart inboxes, integration with Calendar, modal keyboard shortcuts (they aren't operative when you're typing in a text box but are active otherwise) and non-intrusive threading (conversation-view). The fact that all this is the same on my Macbook Pro, on my Arch Linux desktop, or when I reboot to Windows, without any effort on my part to synchronize settings makes this all rather excellent.
- jagermo 11y ago
  Same here. I use at least 2 PCs as well as mobile Systems. I love to have the same data everywhere without having to sync something. That beeing said, I wouldn't mind running my own webmailer as long as it has most of the google apps/office 365 features. I'm hoping for mailpile myself even if it still takes some time.
- TsiCClawOfLight 11y ago
  Except for the split inboxes, I have all of that in Thunderbird with lightning.
viraptor 11y ago
My main issue is that search and labels just don't work as well as in gmail webapp. Also, I'm sending 90% of emails from my phone anyway and I don't know of any good client that works both with gmail (with transparent caching of recent/viewed messages) and gpg.
- 11y ago

leni536 11y ago

I tried to use gnupg but can't wrap my head around the web of trust. My main concern of WoT: What my signature of an other guy's public key actually means? My takeaway is that there is an implicit statement that you sign, but I don't really know what it is. According to the gnupg privacy handbook[1] this statement is roughly "I trust that this guy can properly sign other stuff" which is kind of recursive, but I like it. But when you validate if a message is really written buy a guy named John Doe then the trust path doesn't actually verify this. The trust path verifies that this guy who claims to be John Doe is good at signing other guy's keys. I don't care about that at this point. Of course people don't actually think of the statement written in the privacy handbook, they implicitly sign the statement "I trust that this guy can properly trust other stuff and I know that this guy's name is what he currently has as an ID.". There are several problems with this in practice: - Now you are signing two statements with one signature and you can't separate the two. Now using anonymous public keys becomes tricky as you lose one half of your statement. - Signing the id happens at the wrong place. Malory can revoke her identity than push "Barack Obama" as her new id, now she can send messages in the name of the president. Of course in practice it's hard, because you can't delete revoked ids from key servers. But at this point you trust the key servers. I thought that key servers are not trusted part of PGP. - gnupg guys advocate key signing parties: you gather at one place, bring your ID then sign each other's keys. The problem with this that you only verify half of your statement (id). The other half is tricky to verify (Can this guy properly protect his priv key? Will this guy just randomly sign everything he sees?), I think it makes more sense to trust a friend who you already know well. Of course there are trust levels and I think you should only use marginal trust at these parties, however I don't know what's the practice. - There are keys that are not tied to people, they are typically tied to software packages. Now what does it mean when someone signs such a key? Take putty as an example. Its master key is signed by several people. Each signature could mean that "this is the putty project's master key that is used to sign the binaries themselves" which can be verified by the given guy knowing the developer and that he is trustworthy (at this point PGP is misused though, the guy should have signed the developer's key instead and only the developer should sign the binary signing key, but it would make trust paths longer). It could also mean that "I trust that PuTTY is a great software and doesn't do anything nasty behind your back" which requires an entirely different verification. In the end the trust path a way too simplified projection of these statements and most likely you can't actually verify the statement that you care about. [1] https://www.gnupg.org/gph/en/manual.html#AEN282 https://www.gnupg.org/gph/en/manual.html#AEN282

viraptor 11y ago

FAQ is a bit confusing. They say there's only one keyring, but at https://github.com/google/end-to-end/wiki/Keyring https://github.com/google/end-to-end/wiki/Keyring they admit it was not a great idea and that they're splitting the responsibilities. Based on the last planned implementation (External Key Manager (GnuPG bridge, other hardware, network oracle etc..)), I hope it will "just work" with hardware keys.

koto1sa 11y ago
One of the developers here: Yes, the Keyring reimplementation is in progress and ends very soon. After the redesign, applications built on top of E2E library will be able to use different sources of both public and private keys (so it's easy to do integrations with GnuPG, hardware keys HKP, or e.g. Facebook). The API will be similar to what's in https://github.com/google/end-to-end/wiki/Keyring https://github.com/google/end-to-end/wiki/Keyring.
- mikekchar 11y ago
  One thing that is currently missing from E2E (as far as I can tell having played with it a little in the last month) is any kind of web of trust. When I import a key, I can't tell if it has been signed by me or someone I trust. Is this on the radar for the UI after the Keyring reimplementation is finished? At the moment, what we've suggested at our work is that people manage keys in GPG and then only export keys into E2E if they trust them. But it would be nice be able to do those kinds of things in E2E (or at least be able to tell if a key was signed by me). BTW, thanks for working on this!
  - koto1sa 11y ago
    See https://github.com/google/end-to-end/wiki/Key-Distribution https://github.com/google/end-to-end/wiki/Key-Distribution. In short, we don't invest much into WoT.
    - timboslice 11y ago

mtgx 11y ago

Good to see that E2E has been progressing, but I still wish we had a PFS alternative to PGP. With today's hacks and the total state of surveillance in which we are in, it's a little crazy to expect people to use the same key 10+ years without it getting compromised. Even a year seems too much.

kweks 11y ago

It's worth mentioning Mailvelope ( https://www.mailvelope.com/ https://www.mailvelope.com/ ) - Free - Supported in FF / Chrome - Supports Gmail, Yahoo, Outlook and GMX I've been using it extensively for about 12 months now. It's solid, unobtrustive, and just .. works. Decryption of attachments would be nice, but it's definitely not a deal breaker.

mikekchar 11y ago
Signing of encrypted messages is not supported at the moment. Unfortunately that's a deal breaker for me :-( But it does look very nice.
- kweks 11y ago
  Plain vanilla signing obviously works, and you could (and can, according to a quick check) - just paste your encrypted message back into the window and sign it (unless I grossly mis-understand signing, which I might do..)
brightsize 11y ago
FWIW Mailvelope also works fine with Fastmail in my experience.

chromano 11y ago

There's no way I'd share my private key with whatever extensions there are. It just doesn't feel right.

feld 11y ago

Wait, you have to install a JDK to use this chrome extension?

lallysingh 11y ago
No, to build the chrome extension from source.
- feld 11y ago
  oh, thanks for clarifying.

drdaeman 11y ago

Does it use inline PGP or PGP/MIME? (On an unrelated note, I wonder if there's anything on mobile that supports PGP/MIME. K-9 Mail only knows about inline.)