So, following on from the theme of other week’s post, this is a very quick plugin which will opportunistically encrypt email sent by Known.

It works in much the same way as the similar WordPress code; if a key for a user is in the keyring, the email is encrypted before it is sent. It is particularly handy when combined with my PGP Signin code, since that will provide key discovery.

I wrote this for my own use, so it’s not perfect. For example, since Known sends all email as HTML (unless my plain text email patch is also applied this patch was merged into core), my plugin currently just strips tags, which at least makes the email somewhat readable.

Anyway, kick it around.

» Visit the project on Github...

On the Indiewebcamp wiki, there’s a page discussing HTTPS, the support for which is strongly recommended. As I’ve mentioned previously, at this stage all non-encrypted communication forms (including traditional port 80 HTTP) should be considered deprecated and dangerous.

Indieweb compatible sites are encouraged to get a higher level as possible, and thanks to some prodding, I’ve finally moved both this blog and my feed over to HTTPS only, with HSTS and forward secrecy.

This got me thinking, perhaps it would be worth adding a “Level 7” (or perhaps Level 6.5) to this, and to suggest that Indieweb sites should also be made available as .onion hidden services on Tor?


  • Anonymity. Would go a large way towards protecting communication metadata (who know’s whom), which is a goal we should move towards in a world of endemic selector based surveillance.
  • Encryption. Traffic within the tor network is end to end encrypted, and there is some discussion of whether this renders HTTPS unnecessary.


  • Tor has nothing to do with HTTPS, although it is encrypted. However, the HTTPS levels page seemed a good place to put the suggestion.
  • Could be seen as endorsing one service. Tor is Free software and is pretty much the only game in town when it comes to anonymity networks, but does that constitute a silo? Probably not, but is a point for discussion.
  • No certificates for .onion. There are currently no certificate providers available for .onion domains. But, this may not be a problem.

Anyway, just mooting this as a point for discussion.

We all know how important it is to secure web servers with encryption. As I’ve mentioned before, port 80 HTTP should be considered deprecated at this point!

Just as important (potentially more so), but often overlooked, is to ensure that your email server is also secure.

STARTTLS is a technology that lets you start an encrypted session during a standard SMTP connection. In the same way as HTTPS secures web, STARTTLS will secure email in transit from your mail client to the server, and from server to server. This makes it much harder to passively read the traffic, and having more encrypted traffic on the internet is only ever a good thing.

This only protects email in transit from server to server of course, so this is not a replacement for end to end encryption methods like PGP, but it does complement it… and since most email is still sent insecurely, this adds extra security without requiring your users do any extra work.

It’s easy to set up (for Exim at least), and it transparently runs on port 25, so there’s no reason not to!

Generate your keys

As with web, you’ll need a server key and certificate file.

For my public mail and MX relay servers, I decided to use valid certificate authority certificates. Clients, and some relaying servers, will throw a certificate error for self signed certificates, but others will not. Better safe than sorry, and since I already had a valid certificate on my site for the server in question, I simply recycled the certificate.

If this is your internal server, you can use a certificate signed by your own certificate authority, supported by the machines in your organisation.

The default exim configuration expects to find certificates in /etc/exim4/exim.key and /etc/exim4/exim.crt.

Enable TLS

The basic STARTTLS configuration by simply editing exim4.conf.template and setting MAIN_TLS_ENABLE = yes in the tlsoptions section. Restart exim and you should have STARTTLS support enabled.

As with a web server, you can configure ciphers etc at this stage. On my server at least, the defaults seemed reasonably strong, but as we learn which ciphers have been compromised by GCHQ and the NSA, we might need to tweak these.

Test your configuration

Next, you should test your configuration.

To do this, the simplest way is to use a program called swaks, which you should find in your distro’s package library.

Should produce a result something like…

If you get an error when starting TLS examine your exim log for the cause.