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This article ignores certified email built into almost every email client. I recently experimented with Thunderbird and Mac Mail because I wanted to set up enc

This article ignores certified email built into almost every email client. I recently experimented with Thunderbird and Mac Mail because I wanted to set up encrypted email, and I wanted to move from GMail to one of my domains through RunBox. Both clients are set up for encrypted email through certificates. The UI is pretty slick in both cases, the docs looked pretty clear! What I found as I tried to send an email saddened me: obtaining a signed personal certificate with a CA is nigh impossible (self-signed is easy, but useless). I have some friends in the military who's certs are on my keychain because they are signed by .mil, but for us schlubs? There's really no alternative that I could find that is trusted. Seems like if personal certs could be offered by a reliable CA, it would be pretty damn easy to use encrypted email.

inetknght 6y ago
I'm lucky enough to still have a job in a crisis. If that weren't the case, then a pet project of mine would be a LetsEncrypt-like service for personal certificates. Certificates you could install in your browser for TLS authentication, and some templates and examples showing how to configure nginx to authorize clients using one. I imagine email would be pretty similar. I'm just not as familiar with how to configure email clients to use certificates.
- floatingatoll 6y ago
  There were several free SMIME certificate providers, who would issue you a personal certificate verifying that you control a given email address. Most have shutdown their free products in the past few years, I suspect as a result of having to invest money in their decades-old web applications that no longer function correctly in modern browsers. One remains, but this blog post warns that they practice unsafe private key practices, so I'm inclined to suggest that none do. https://davidroessli.com/logs/2019/09/free-smime-certificates-in-2019/ https://davidroessli.com/logs/2019/09/free-smime-certificate...
- WorldMaker 6y ago
  "LetsEncryptEmail" sounds like a good idea. It seems like there would be lessons to learn from Mozilla's Persona / BrowserID project which followed similar goals at a technical level. For instance, in addition to falling back to OTP codes sent to an email address for verification, they had a reasonably smart idea that you could use OIDC ("OpenID Connect") to validate logins more directly to at least major email providers like Gmail and Yahoo since many of the majors do have an OIDC endpoint or two. (Mozilla Persona was a great project idea and a shame it never got enough market share. It didn't end up using personal certificates, though IIRC they explored that as an option and what they did use was technically very close.)
- jamieweb 6y ago
  I remember reading about Individual Validation (IV) certificates, which I believe were similar to Extended Validation (EV) certificates, but for individuals. I don't think they ever really took off (or even existed), and there isn't anything in the Baseline Requirements / EV Guidelines as far as I know. Nowadays they seem to be a bit of a myth, as there is very little evidence of them online except for use in code signing.
- tialaramex 6y ago
  In principle nothing stops you creating such a CA. The problem is, nothing stops anybody else creating such a CA. Why should I trust either of them? Why should anybody? Unless a critical mass trust the same CAs it's hopeless. What you need there is a PKI, a Public Key Infrastructure. A PKI has two components, firstly some technical agreements like what sort of certificates are used, how to write email addresses and so on, for which you can mostly rely upon PKIX in this scenario - but then you also need some consensus on the much more difficult and political trust problem. Mostly what happens is that PKIs are relatively small and private. EMV ("Chip and PIN" cards) has its own private PKI managed by EMVCo, the RIRs have one for route management called RPKI, lots of businesses have their own. Apple and Microsoft operate PKIs for "code signing" of various sorts. And there's one obvious public PKI, the Web PKI, which is why your browser agrees with mine that this is https://news.ycombinator.com/ https://news.ycombinator.com/ But there isn't one for email. So the far trickier problem than spinning up some "LetsEncrypt like service for personal certificates" is building that PKI.
jschwartzi 6y ago
CA certificate signing is orthogonal to encryption. If you only need to encrypt an email then a public key is sufficient. However if you also need a proof that you are who you say you are, then you would need a certificate that is authenticated by your PKI plus a public encryption key. It's strange to me that any tool that simply encrypts email requires a CA-signed certificate instead of a simple public key or a self-signed certificate. Self-signing is totally okay provided you have a way to distribute your certificate that allows the recipient to authenticate that it came from you. Then they can simply add your certificate to their list of trusted certificates.
- 0xff00ffee 6y ago
  > CA certificate signing is orthogonal to encryption. Yes in the broad sense and no in the specific case. In order to activate macOS Mail encryption you need a certificate on your keychain. So by having a CA issue you a certificate, the mail client can generate the keys to encrypt that mail without additional passwords (e.g., relying on in-situ authentication). So in this application they are interrelated.
- techntoke 6y ago
  Or you know, just use PGP/GPG (which have public keyservers) and forget about CA.
  - 0xff00ffee 6y ago
    Because that brings us to square one again, which is the article. You need a CA, PGP/GPG construct their own federated "CA" like entity, but its the same thing.
    - techntoke 6y ago
      You don't need a CA for PGP/GPG. In fact, it is generally advisable to never trust a CA for public keys. However, it is common to utilize the fingerprint to verify the key from a public server that has been provided by the user. Ideally though, you'd never trust an email provider to maintain a CA of keys that you'd actually use to send a confidential message.
firebird84 6y ago
Did you try instantssl? https://secure.instantssl.com/products/frontpage?area=SecureEmailCertificate https://secure.instantssl.com/products/frontpage?area=Secure...
- deleted 6y ago
  [deleted]
- 0xff00ffee 6y ago
  Weird, that was surprisingly easy. Wonder why that didn't show up in my search...
  - firebird84 6y ago
    I had to spend some time searching myself. I used to use Comodo's free certs back when they were still called Comodo. All these changes seem to have made things difficult.
indymike 6y ago
A LetsEncrypt for email would be a game changer.

inetknght 6y ago

I'm lucky enough to still have a job in a crisis. If that weren't the case, then a pet project of mine would be a LetsEncrypt-like service for personal certificates. Certificates you could install in your browser for TLS authentication, and some templates and examples showing how to configure nginx to authorize clients using one. I imagine email would be pretty similar. I'm just not as familiar with how to configure email clients to use certificates.

floatingatoll 6y ago
There were several free SMIME certificate providers, who would issue you a personal certificate verifying that you control a given email address. Most have shutdown their free products in the past few years, I suspect as a result of having to invest money in their decades-old web applications that no longer function correctly in modern browsers. One remains, but this blog post warns that they practice unsafe private key practices, so I'm inclined to suggest that none do. https://davidroessli.com/logs/2019/09/free-smime-certificates-in-2019/ https://davidroessli.com/logs/2019/09/free-smime-certificate...
WorldMaker 6y ago
"LetsEncryptEmail" sounds like a good idea. It seems like there would be lessons to learn from Mozilla's Persona / BrowserID project which followed similar goals at a technical level. For instance, in addition to falling back to OTP codes sent to an email address for verification, they had a reasonably smart idea that you could use OIDC ("OpenID Connect") to validate logins more directly to at least major email providers like Gmail and Yahoo since many of the majors do have an OIDC endpoint or two. (Mozilla Persona was a great project idea and a shame it never got enough market share. It didn't end up using personal certificates, though IIRC they explored that as an option and what they did use was technically very close.)
jamieweb 6y ago
I remember reading about Individual Validation (IV) certificates, which I believe were similar to Extended Validation (EV) certificates, but for individuals. I don't think they ever really took off (or even existed), and there isn't anything in the Baseline Requirements / EV Guidelines as far as I know. Nowadays they seem to be a bit of a myth, as there is very little evidence of them online except for use in code signing.
tialaramex 6y ago
In principle nothing stops you creating such a CA. The problem is, nothing stops anybody else creating such a CA. Why should I trust either of them? Why should anybody? Unless a critical mass trust the same CAs it's hopeless. What you need there is a PKI, a Public Key Infrastructure. A PKI has two components, firstly some technical agreements like what sort of certificates are used, how to write email addresses and so on, for which you can mostly rely upon PKIX in this scenario - but then you also need some consensus on the much more difficult and political trust problem. Mostly what happens is that PKIs are relatively small and private. EMV ("Chip and PIN" cards) has its own private PKI managed by EMVCo, the RIRs have one for route management called RPKI, lots of businesses have their own. Apple and Microsoft operate PKIs for "code signing" of various sorts. And there's one obvious public PKI, the Web PKI, which is why your browser agrees with mine that this is https://news.ycombinator.com/ https://news.ycombinator.com/ But there isn't one for email. So the far trickier problem than spinning up some "LetsEncrypt like service for personal certificates" is building that PKI.

jschwartzi 6y ago

CA certificate signing is orthogonal to encryption. If you only need to encrypt an email then a public key is sufficient. However if you also need a proof that you are who you say you are, then you would need a certificate that is authenticated by your PKI plus a public encryption key. It's strange to me that any tool that simply encrypts email requires a CA-signed certificate instead of a simple public key or a self-signed certificate. Self-signing is totally okay provided you have a way to distribute your certificate that allows the recipient to authenticate that it came from you. Then they can simply add your certificate to their list of trusted certificates.

0xff00ffee 6y ago
> CA certificate signing is orthogonal to encryption. Yes in the broad sense and no in the specific case. In order to activate macOS Mail encryption you need a certificate on your keychain. So by having a CA issue you a certificate, the mail client can generate the keys to encrypt that mail without additional passwords (e.g., relying on in-situ authentication). So in this application they are interrelated.
techntoke 6y ago
Or you know, just use PGP/GPG (which have public keyservers) and forget about CA.
- 0xff00ffee 6y ago
  Because that brings us to square one again, which is the article. You need a CA, PGP/GPG construct their own federated "CA" like entity, but its the same thing.
  - techntoke 6y ago
    You don't need a CA for PGP/GPG. In fact, it is generally advisable to never trust a CA for public keys. However, it is common to utilize the fingerprint to verify the key from a public server that has been provided by the user. Ideally though, you'd never trust an email provider to maintain a CA of keys that you'd actually use to send a confidential message.

firebird84 6y ago

Did you try instantssl? https://secure.instantssl.com/products/frontpage?area=SecureEmailCertificate https://secure.instantssl.com/products/frontpage?area=Secure...

deleted 6y ago
[deleted]
0xff00ffee 6y ago
Weird, that was surprisingly easy. Wonder why that didn't show up in my search...
- firebird84 6y ago
  I had to spend some time searching myself. I used to use Comodo's free certs back when they were still called Comodo. All these changes seem to have made things difficult.

indymike 6y ago

A LetsEncrypt for email would be a game changer.