Some notes on LetsEncrypt

December 22, 2015

I’ve been playing with LetsEncrypt for a bit now, and on the whole, I like it. However, it’s still early days, and I wanted to share my experiences.

For the examples I use, I’m looking at my own set-up (or more precisely, NO2ID’s, which I superintend/am Tech Director of) — I find real examples are useful.

Debian & Python

I started using wheezy but took this as an opportunity to upgrade to jessie; I wanted Apache 2.4, as well as a more modern version of Python.

(You might want to upgrade first; it’ll make your life easier.)

Python versions are quite important, too: if you start on an older version, it’s probably advisable to zap (rm) your virtualenv (/root/.local/…), after upgrading — it saves a lot of time and frustration.

You don’t want to run into the urllib3/OpenSSL issues that are loosely documented, but not always obvious; use Python 2.7.9 (or more recent) and save yourself some ballache.

A REQUIREMENTS file might be useful (and even better, say, a REQUIREMENTS.{debian,centos,freebsd,macos,ubuntu} file).

Rate limits

There are rate limits.

However, it seems that the documentation (and the recommended tool) doesn’t deign to mention this. Nor does letsencrypt-auto default to using the staging infra (use letsencrypt-auto --server

In the real-world, we should accept that people will go for the easy option, and no one reads long documents like terms and conditions. Especially not when one needs to view a PDF and is working entirely in a console.

The rate limits really hit me, and prevented an earlier adoption, as I created too many in live, not staging, especially at first, and when I had a “broken” (not to what letsencrypt could parse) configuration.

Error messages

Aren’t always that helpful or very useful, and not helped by information being scattered around in:

  • the RTD
  • the GitHub README
  • Python module docs (see below)
  • Source code comments (which wretched part’s causing this so I can dig more)
  • Your letsencrypt log file, even with --verbose being passed as an ARG
  • IRC
  • A few StackOverflow questions + answers
  • The forum (and issues with how up to date is this; is it canonical; gah, searching; it’s not stackoverflow)

— or not existing at all.

This (lack of documentation, and left to fend for oneself), I think represents a real problem: especially if ordinary users (including the sort who screen grab terminal outputs (rather than just fucking copy and pasting — or even pipe-ing to pastebin/gists)) are going to use things.

At least there’s not a Mailing list, as well as the forum, or worse, the mailing list (archive) being syndicated to seventeen different forums.


In this case, I still use Apache. At some point, I’ll be switching over to nginx, as I prefer nginx, and find it faster, but ho-hum. At time of writing, nginx support isn’t as fully fledged as Apache, at least according to the docs (I have a hatred of forums).

There are some gotchas to be aware of, that are loosely documented, but have atrocious error messages that are, quite plainly misleading.


You may need to bind Apache to use an IPv4 address of your interface to get things working.

	<IfModule ssl_module>
		Listen 443

	<IfModule mod_gnutls.c>
		Listen 443

	<IfModule mod_ssl.c>
		Listen 443


	<IfModule ssl_module>

	<IfModule mod_gnutls.c>

	<IfModule mod_ssl.c>

(a plain Listen 443 in ports.conf didn’t help)

Config files and quoting

If you have Rewrites in your configs, make sure they’re quoted.

e.g, apachectl configtest will let you have something like

    RewriteRule ^index\.php$ - [L]
    RewriteRule ^wp-admin$ wp-admin/ [R=301,L]
    RewriteCond %{REQUEST_FILENAME} -f [OR]
    RewriteCond %{REQUEST_FILENAME} -d
    RewriteRule ^ - [L]
    RewriteRule ^(wp-(content|admin|includes).*) $1 [L]
    RewriteRule ^(.*\.php)$ $1 [L]
    RewriteRule . index.php [L]

but to get letsencrypt-auto (or letsencrypt --apache) to run, you’ll need

    RewriteRule "^index\.php$" "-" [L]
    RewriteRule "^wp-admin$" "wp-admin/" [R=301,L]
    RewriteCond "%{REQUEST_FILENAME}" "-f" [OR]
    RewriteCond "%{REQUEST_FILENAME}" "-d"
    RewriteRule "^" "-" [L]
    RewriteRule "^(wp-(content|admin|includes).*)" "$1" [L]
    RewriteRule "^(.*\.php)$" "$1" [L]
    RewriteRule "." "index.php" [L]

(for WordPress — why on earth one would put these in a .htaccess file when one can chuck ‘em in the vhost config…)

The error message here, is something along the lines of ‘Apache not found’.


There’s an optional setting to define a rewrite to take insecure visitors to the secure version of the site.

This balks if you already have some, and isn’t particularly good; as well as not leaving things in what I’d say is not an ideal state, especially if you have a lot of Rewrites (and you’ll want to check in your -le-ssl.conf that these now point to https:// not http://).

In an ideal world, something like

<VirtualHost *:80>
	Redirect		/foo	/baa
	Redirect		/one	/two
	Redirect		/join
	RewritePermanent	/baz	/downloads/baz


<VirtualHost *:443>
	Redirect		/foo	/baa
	Redirect		/one	/two
	Redirect		/join
	RewritePermanent	/baz	/downloads/baz

<VirtualHost *:80>
	RewriteEngine on
	RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [L,QSA,R=permanent]

would be awesome.


Constant update

On every run. So annoying. I wish this would timestamp, and just check once an hour/day/week…

Revoking certificates

There’s very little documentation on this, and I didn’t find it particularly useful / working.

Which cert file should you pass as your parameter? (discovered via IRC)

./letsencrypt-auto revoke --cert-path /etc/letsencrypt/archive/

seemed to revoke, but the certificates were still offered when I tried to create again. A --delete option might be useful in future versions.

You may want to do something involving find and xargs (in /etc/letsencrypt/), but y’know, YMMV.

In testing, I wasn’t too bothered, so did the LazyThing™ and issued and rm -r /etc/letsencrypt but you don’t just copy and paste things you read on the intertubes, do you?

It’d be nice if there were a curses interface for revocation.

No wildcard support (yet)

But see below…

Defining the ‘master’ certificate

Let’s say you’re mitigating against the wildcard lack-of-support; and you want to have various sites on the same cert; no problem, except you might want to use the root domain, not a subdomain as the main factor here; I found a two-step approach works here:

  1. Create using apex and www (e.g. and
  2. When that’s done, re-run and extend the certificate to include others (,,; but note, if you don’t want punters to see you have a cert for don’t include that; of course, security through obscurity is not especially useful; YMMV. Create an extra cert (but note ratelimit) for say dev and administrative things.

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