Using LetsEncrypt

Lets Encrypt is a new service to provide free SSL keys [1]. I’ve just set it up on a few servers that I run.


The first thing to note is that the client is designed to manage your keys and treat all keys on a server equally with a single certificate. It shouldn’t be THAT difficult to do things in other ways but it would involve extra effort. The next issue that can make things difficult is that it is designed that the web server will have a module to negotiate new keys automatically. Automatically negotiating new keys will be really great when we get that all going, but as I didn’t feel like installing a slightly experimental Apache module on my servers that meant I had to stop Apache while I got the keys – and I’ll have to do that again every 3 months as the keys have a short expiry time.

There are some other ways of managing keys, but the web servers I’m using Lets Encrypt with at the moment aren’t that important and a couple of minutes of downtime is acceptable.

When you request multiple keys (DNS names) for one server to make it work without needless effort you have to get them all in the one operation. That gives you a single key file for all DNS names which is very convenient for services that don’t support getting the hostname before negotiating SSL. But it could be difficult if you wanted to have one of the less common configurations such as having a mail server and a web server on the same IP addess but using different keys

How To Get Keys

deb testing main

The letsencrypt client is packaged for Debian in Testing but not in Jessie. Adding the above to the /etc/apt/sources.list file for a Jessie system allows installing it and a few dependencies from Testing. Note that there are problems with doing this, you can’t be certain that all the other apps installed will be compatible with the newer versions of libraries that are installed and you won’t get security updates.

letsencrypt certonly --standalone-supported-challenges tls-sni-01

The above command makes the letsencrypt client listen on port 443 to talk to the Lets Encrypt server. It prompts you for server names so if you want to minimise the downtime for your web server you could specify the DNS names on the command-line.

If you run it on a SE Linux system you need to run “setsebool allow_execmem 1” before running it and “setsebool allow_execmem 0” afterwards as it needs execmem access. I don’t think it’s a problem to temporarily allow execmem access for the duration of running this program, if you use KDE then you will be forced to allow such access all the time for the desktop to operate correctly.

How to Install Keys

[ssl:emerg] [pid 9361] AH02564: Failed to configure encrypted (?) private key, check /etc/letsencrypt/live/

The letsencrypt client suggests using the file fullchain.pem which has the key and the full chain of certificates. When I tried doing that I got errors such as the above in my Apache error.log. So I gave up on that and used the separate files. The only benefit of using the fullchain.pem file is to have a single line in a configuration file instead of 3. Trying to debug issues with fullchain.pem took me a lot longer than copy/paste for the 3 lines.

Under /etc/letsencrypt/live/$NAME there are symlinks to the real files. So when you get new keys the old keys will be stored but the same file names can be used.

SSLCertificateFile "/etc/letsencrypt/live/"
SSLCertificateChainFile "/etc/letsencrypt/live/"
SSLCertificateKeyFile "/etc/letsencrypt/live/"

The above commands are an example for configuring Apache 2.

smtpd_tls_cert_file = /etc/letsencrypt/live/
smtpd_tls_key_file = /etc/letsencrypt/live/
smtpd_tls_CAfile = /etc/letsencrypt/live/

Above is an example of Postfix configuration.

ssl_cert = </etc/letsencrypt/live/
ssl_key = </etc/letsencrypt/live/
ssl_ca = </etc/letsencrypt/live/

Above is an example for Dovecot, it goes in /etc/dovecot/conf.d/10-ssl.conf in a recent Debian version.


At this stage using letsencrypt is a little fiddly so for some commercial use (where getting the latest versions of software in production is difficult) it might be a better option to just pay for keys. However some companies I’ve worked for have had issues with getting approval for purchases which would make letsencrypt a good option to avoid red tape.

When Debian/Stretch is released with letsencrypt I think it will work really well for all uses.

3 comments to Using LetsEncrypt

  • Donald Gordon

    You can get the letsencrypt client to write its challenge files out to your web-root — they go in a directory called .well-known/acme. I’ve done this with HAProxy forwarding only requests for that folder to webfs, and all other traffic on to the “real” server.

    You can also run the client multiple times to get multiple certificates, if you want to have a different certificate for your mailserver. As long as your web server will serve up the .well-known/acme folder when presented with an appropriate Host: header, it should all work.

  • Akshay Kumar

    Does this work with Nginx ?


    There is no nginx package similar to the above, and from the design of nginx there might never be.

    The method of writing challenge files to the web root should work with nginx and the method that I’ve used so far of stopping the web server before running the letsencrypt client will work too.