Letsencrypt on Debian 10 – switching to new ‘snap’ based Certbot

Official instructions: https://certbot.eff.org/lets-encrypt/debianbuster-nginx

If you’ve upgraded a machine Debian 10 (Buster) or later you’ll see a warning like this:

/etc/cron.weekly/certbot:
Your system is not supported by certbot-auto anymore.
certbot-auto and its Certbot installation will no longer receive updates.
You will not receive any bug fixes including those fixing server compatibility
or security problems.
Please visit https://certbot.eff.org/ to check for other alternatives.

Certbot, the tool for updating Let’s Encrypt certificates, is now distributed via Snap.  If you haven’t heard of that, Snap is a new package format – the point is it’s more cross platform – so a single package will currently support Ubuntu, Debian, Fedora, Arch Linux, Manjaro, and CentOS/RHEL.  More details >

This means you need to:

then, typically you already have a weekly cron file that calls certbot to renew the certificates, and restarts your apache or nginx server (the latter step is important because otherwise it’ll keep serving a cached copy of the old certificate, which will eventually expire).

Here’s the (old) contents of my /etc/cron.weekly/certbot:

#!/bin/bash
/home/william/letsencrypt/certbot-auto renew
service nginx reload

You need to remove the line calling certbot-auto, but leave the one restarting nginx once a week.  You might choose to rename the cron file or add a comment to make it clearer to your future self why it’s needed.

Next, check snap is to up to date:

sudo snap install core; sudo snap refresh core

Install the certbot package:

sudo snap install --classic certbot

Then you can test a manual update either:

sudo certbot certonly --nginx

(on the interactive version you’re presented with a list of sites to choose from)

Finally, do a renewal “dry-run” to check for problems:

sudo certbot renew --dry-run

The key points about dry-runs:

  • they use the Let’s Encrypt staging environment, so you don’t hit rate limits
  • therefore, real certificates aren’t requested or saved
  • it’s basically testing that Let’s Encrypt end is able successfully handshake with your server, can write files to correct places etc.

Renewals

Renewals can use one of three methods: crontab, cron files or systemctl timers.

On the servers I’ve installed so far, certbot has automatically setup a timer. You can verify it has by running systemctl as follows:

$ systemctl list-timers
NEXT LEFT LAST PASSED UNIT ACTIVATES
Mon 2021-02-15 12:12:00 GMT 1h 43min left Mon 2021-02-15 07:57:03 GMT 2h 31min ago snap.certbot.renew.timer snap.certbot.renew.service
```

So certificate refreshes will happen automatically, but remember you need to handle regularly restarting your web server (and weekly is as good an interval as any to do that).

Here’s another link to the documentation:
https://certbot.eff.org/lets-encrypt/debianbuster-nginx

HowTo: Nginx with HTTP2 support on Debian Jessie

The original problem:

  • SPDY has been replaced by HTTP2, which is better in a number of ways
  • As of June 2016, Chrome has dropped support for SPDY
  • HTTP2 uses ALPN
  • ALPN requires OpenSSL 1.0.2
  • Debian Stable (aka Jessie aka v8) and others OSes only had 1.0.1

What’s changed:

Procedure:

  • Add jessie-backports and jessie-nginx-http2 (ansible playbook)
  • Upgrade openssl them from the correct place: sudo apt-get install -t jessie-backports openssl
  • sudo apt-get install nginx-full (which should pull in various libnginx-mod packages)
  • Change any references in your Nginx config files from spdy to http2
  • Run sudo nginx -t to verify the configuration is valid
  • Start server

Verify HTTP2 is working (Chrome or Opera):

Developer Tools, Network tab, reload page, enable the Protocol column, look for H2, which means HTTP2.

Extra step for LetsEncrypt / Certbot compatibility:

A few days after doing this I got the following error when my weekly cronjob for renewing LetsEncrypt certificates ran:

    build/temp.linux-x86_64-2.7/_openssl.c:415:30: fatal error: openssl/opensslv.h: No such file or directory
     #include <openssl/opensslv.h>

And on running it manually I had this:

The following packages have unmet dependencies:
 libssl-dev : Depends: libssl1.0.0 (= 1.0.1t-1+deb8u6) but 1.0.2k-1~bpo8+1 is to be installed
 Recommends: libssl-doc but it is not going to be installed

The solution was just to pull in libssl-dev from jessie-backports too:

apt-get install -t jessie-backports libssl-dev

Note, in my case, I have a git clone of certbot rather than a packaged version, though it is now available as a backport for Debian Jessie.

Let’s Encrypt news – client name change and auto renewals

Updated Wed 14 Sep 2016 (new installation guide URL, clarify name change.)

Let’s Encrypt have updated their getting started page, but the following may help anyone trying to understand the latest changes.

If you’re installing from scratch, use Certbot (see below) and start here.  You’ll get custom instructions for your operating system and web server – the client can now be installed via a package on newer systems.

The name

The client (now at version 0.6.0) from letsencrypt-auto to Certbot – to be precise, the project/ecosystem is still called Let’s Encrypt, while Certbot is the EFF’s certificate deployment client.

You’ll find that certbot-auto (a shell script) is an exact copy of the letsencrypt-auto, so all previous commands will still work.

The git repository has also been renamed – the old one is redirected.

Old: https://github.com/letsencrypt/letsencrypt
New: https://github.com/certbot/certbot

You can update the location of your ‘origin’ remote in .git/config

Renewals

You can now renew all your certificates at once.

# to test
~/letsencrypt/certbot-auto renew --dry-run

# to actually do it
~/letsencrypt/certbot-auto renew

There’s some clever stuff going on here:

  • It uses all your previous settings.
  • It renews any certificates that will expire within 30 days.
  • Afterwards you get a list of which were renewed and which were skipped (“not due for renewal yet”)
  • --dry-run  use staging server, so doesn’t count towards API limits.
  • “renew” is designed for unattended use.
  • Remember you still need to reload apache/nginx afterwards.

Example of a cron.weekly script you could use:

#!/bin/bash
/path/to/letsencrypt/certbot-auto renew
service nginx reload

Introduction to Let’s Encrypt (and a few tips)

Note: this isn’t a How To or Getting Started guide – be sure to use the official documentation.  Updated Sun 25 Mar 2018.

13 May 2016 – see my summary of the latest changes.

Simpler installation process

Let’s Encrypt has been packaged on newer Linux systems – you no longer need to do manual installation. E.g, on Ubuntu 16.04 (Xenial) you can now simply do:

sudo apt-get install letsencrypt

The Certbot installation page prompts you to choose your web server and operating system/version and provides tailored instructions.

What is Let’s Encrypt?

Let’s Encrypt is a free and automated Certificate Authority.  Providing you run your own virtual or dedicated Linux server, you can quickly create and renew certificates for any domains (or subdomains) hosted on it.

Why use it (and why use https)?

Let’s Encrypt is completely free, whereas the cheapest certificates I’m aware of are currently £30+VAT per year for a single (sub)domain certificate or £80+VAT/year for a wildcard (*.example.com)

Until now, that’s made it common to avoid using https:// unless absolutely necessary – e.g. you have a customer database.  As the old process, described below, often involves clients, it can add the burden of justifying to them why spending the extra money is worthwhile.

Now, you can use TLS (https://) everywhere as standard and take advantage of the features of SPDY and HTTP/2, including faster page loads on mobile and a slight boost in your search ranking.  A secure connection also prevents mobile networks or other proxy servers from altering (or breaking) your HTML, changing your cache headers or compressing images.

Getting into the habit of building sites for https:// from the very beginning makes sense as you don’t have to check all your existing pages for insecure content as you do when migrating at a later date – I’d recommend always using a self-signed certificate on your development server.

Once you’re setup and organised – that is, you’ve installed Let’s Encrypt, written and tested a standard set of Apache or Nginx settings and been through the whole process for one domain – adding certificates for subsequent sites is going to take you little more than a minute or so.  Renewing them (note Let’s Encrypt certificates only last 90 days) takes just a few seconds.

By contrast, buying certificates the conventional way is tedious and error prone. You must:

  • pay (which also generates invoices you have to enter as part of your book-keeping)
  • generate and upload a CSR
  • (at a minimum) verify an email address on the domain name (which often involves other people and testing mailboxes in advance)
  • wait for approval and certificate generation (delays of an hour or two are common whenever I do it)
  • manually copy and paste your certificate
  • identify the correct intermediate certificate and add it to your bundle
  • install everything on the sever, check the configuration, reload and hope for the best

Browser support

At the time of writing, Let’s Encrypt is still technically in beta.

Until now, certificates haven’t worked in Windows XP, but this should be resolved by late March 2016. Because of that there are some sites I’ve not migrated from paid certificates yet, and some where I’ve only forced https:// for the admin pages.  For what it’s worth, my approach has been to check analytics data for existing sites but generally just go ahead with new ones – fortunately this won’t be a problem for much longer.

Tips and Troubleshooting

Minimising downtime, keep your existing server running

Originally, it was necessary to use the Let’s Encrypt standalone webserver to generate or renew certificates, which meant turning your existing server off temporarily to free up the port.

This is no longer the the case.  The webroot plugin creates a hidden .well_known directory in your docroot and places static files there as part of an ACME challenge to confirm ownership of the domain – therefore it’s compatible with Apache, Nginx or any other web server.

Directories beginning with a period (.) are usually protected (to stop people browsing .git or .htaccess files) so a brief bit of config is necessary. Nginx example:

location ~ /.well-known {
  allow all;
}

Recommendation: create this directory manually, stick a file in it and verify you can view it in the browser. If you get 403 Forbidden:

  • make sure the directory and files have the correct owner/group and permissions (i.e. can your nginx/www-data etc. user access them?)
  • remember Nginx’s rules about location matching. Are there location blocks earlier in the config that will take precedence over this one?
  • Remember to disable password protection, e.g. with auth_basic off;
  • If your directory is mapped to an alias, rather than a relative location under docroot, try beginning the block with location ^~ instead.

Even if you’re using the standalone server, use the command line switches to save yourself time and manually respond to the prompts.

Why can’t you run the Let’s Encrypt standalone server on some other port so you can leave your web server running? Security.  Ports 80 and 443 are privileged and it would be dangerous for just any user of the server to be able to generate certificates.

Moving servers – remember to turn Certbot off on original machine

If you move a domain from one server to another, you’ll probably remember to install/configure certbot on the new machine, but then may forget to turn it off on the old one.  This doesn’t do any harm – but it does create confusion, because at some point you’ll get an error message like this:

The client lacks sufficient authorization – 404

You may then, as I have, spend a while debugging the old server, before you realise the domain is no longer even mapped to it.

Testing certificate security and compatibility

The Qualys online test is by far the most widely used at the moment.

Opinion: given the variation in the care with which people configure their security certificates, perhaps it’s time the padlock icon changed or degraded in some way to indicate a server where encryption is valid, but vulnerable (RC4 support, for example).  We have taught non-technical users that if the padlock is there, everything is fine, which is often not the case.

Choosing the right encryption protocols

It’s very hard for most people to keep up with the frequent OpenSSL security alerts (and new developments in crytography such as elliptic curve). Worse, there’s a lot of partial advice in circulation – some of it dangerously out of date – about which settings to use.

Remy van Elst has written an excellent excellent guide to maximising your SSL score. <- This is probably the most useful link in the entire post.  Bookmark this site.   He also explains many advanced topics like OCSP Stapling.

Troubleshooting OCSP Stapling

Remember, OCSP won’t work from the very first request after restarting the server, you must allow Nginx a chance to asynchronously query the upstream certificates and cache that data.  So if you’re testing with the openssl command (see below) and it fails straight away, give it a few seconds and repeat.

Similarly, if you are only protecting, say the admin pages of the site, the Qualys SSL Labs test on the https:// version of the homepage can show “OCSP Stapling: No” when you run it, if no-one has visited an https:// protected page recently.

Note the OCSP cache is per Nginx worker, with no sharing between processes.

openssl and SNI

Brief reminder: Server Name Indication allows one server to handle lots of certificates for different domains without needing a separate IP address for each. But it doesn’t work in Internet Explorer up to and including Windows XP (fine in other Windows XP for browsers other than IE, and IE itself supports it as of  Windows 7.)

SNI is pretty standard now, of course.   If you’re running openssl from the Linux CLI, e.g. to test the server’s OCSP response…

openssl s_client -connect example.com:443 -servername example.com -tls1 -tlsextdebug -status | more

…be aware the -servername switch is essential as it indicates which of the available certificates you want, if you don’t specify it Nginx will send back the first one it finds (typically whichever domain is at the beginning of the alphabet, it seems to use the first Listen 443; directive it finds in /etc/nginx/sites-enabled)

Monitoring certificate expiry

Let’s Encrypt will email you shortly before a certificate expires, but if you’re a Nagios user you can test validity yourself using the check_ssl_cert plugin.  Example config:

define service {
    service_description     Certificate - https://wturrell.co.uk
    host_name               turtle2
    check_command           check_ssl_cert!-H turtle2.wturrell.co.uk -n wturrell.co.uk -A -c 7
    use                     daily
}

where -c is the number of days before expiry a critical alert is issued, and daily is a service with a normal_check_interval of 1440 (1440 mins = 24 hrs)

Test output:

SSL_CERT OK - X.509 certificate for 'wturrell.co.uk' from 'AlphaSSL CA - SHA256 - G2' valid until Jul 16 07:25:54 2019 GMT (expires in 1231 days)

(the example I’ve given is a commercially bought certificate, hence the long duration.)

As per the documentation, Let’s Encrypt say they’ll be streamlining the renewal process, and provide an example of a script you could use in the meantime.  I’d still advocate taking responsibility for your own monitoring if you can.

Delete unwanted/old certificates

e.g. if you no longer use a domain, say it was a test domain before the site went live, there’s no longer any need to delete files manually from the various /etc/letsencrypt directories.  First:

cerbot-auto delete

…then choose the certificate you want to remove from the list.

Troubleshooting Let’s Encrypt error messages

The client sent an unacceptable anti-replay nonce :: JWS has invalid anti-replay nonce

Run it again until it works (this was a bug earlier on due to a problem with Let’s Encrypt’s CDN – they’ve fixed that and I haven’t seen it since.)

could not find cert file

Check /var/log/letsencrypt/letsencrypt.log for the precise problem – for example, I’d manually (but only partially) deleted an unwanted certificate and it was still looking for the remainder of that, regardless of which domain I was attempting to renew.

Let’s Encrypt WILL support Windows XP very soon

Update Wed 30 March 2016:  Windows XP browsers ARE NOW SUPPORTED – you don’t need to do anything for this to take effect other than renew your certificate and restart Apache or Nginx.

At present, Let’s Encrypt certificates don’t work on Windows XP (except for Firefox.) This is because IdenTrust, their cross-signatory, requires a certificate extension known as “NameConstraints” to prevent certificates being signed for .mil (or US military) domains.  It looks a bit like this:

Permitted=None
Excluded
     [1]Subtrees (0..Max):
          DNS Name=.mil

Unfortunately XP doesn’t understand this so the certificate breaks.

Anyway, they’ve resolved this nowbut as the certificates will still be from IdenTrust I’m unclear how exactly, the new intermediate certificate won’t have nameConstraints.

This is excellent: it’ll mean there are no real arguments against moving all your existing (paid) certificates over when – or even before – they expire, or adding https:// support to sites without it.

You will need to renew all your certificates to get WinXP support, however one of the advantages of Let’s Encrypt is that the certificates have a short lifetime (3 months), so everyone gets upgraded quickly.  They may make the lifetime shorter in future, if anything.

Note also, the service is still in beta and I would hesitate to criticise them for a problem caused by a deprecated OS, compounded by a political issue.  The rest of the product is already close to perfect.

I have published some Let’s Encrypt tips.