Reverse proxy + Let’s Encrypt CertBot

I have a client who’s using Varnish as a caching reverse proxy for a site which sometimes experiences extremely heavy traffic that the actual web server can’t handle. The client wanted to start offering HTTPS on the website, and I suggested Let’s Encrypt, with its automatically self-renewing 90-day certs, to avoid the yearly hassle of manually renewing certificates with a provider, updating configs, etc.

Varnish does an incredibly good job at handling absurd amounts of traffic… but what it doesn’t do is SSL termination. Nginx, on the other hand, does SSL termination just fine – I’ve had difficulty in the past getting Apache to reverse-proxy HTTPS down to HTTP without hiccups, but it’s a breeze with nginx.

The problem is, how do we get Let’s Encrypt working when it isn’t installed on the root webserver? Certbot’s automatic renewal process depends on updating files on the actual website, in order to demonstrate to the CA that we are who we say we are (since our website is what DNS resolves to). The secret is nginx’s extremely flexible Location blocks, and knowing exactly where CertBot wants to create its identify files for remote verification.

Long story short, we want nginx proxying everything on https://website.tld/ to http//website.tld/ on the back end server. The first step for me was putting an entry in /etc/hosts that points website.tld to the back end server’s IP address ( , not to the front-end proxy’s own ( localhost website-proxy website.tld

That way when we tell nginx that we want it to proxy requests made for website.tld to website.tld, it will correctly connect out to the back end server rather than to itself.

With that done, we create a stub directory for the site using mkdir -p /var/www/website.tld ; chown -R www-data.www-data /var/www and then create a simple site config at /etc/nginx/sites-available/website.tld:

server {
   server_name website.tld;
   root /var/www/website.tld;

   location / {

   location ^~ /.well_known {
     root /var/www/website.tld;

This simple config proxies all requests made to website.tld except those looking for content in or under .well_known – CertBot’s challenge directory – which it serves directly from the local machine itself.

After symlinking the site live and restarting nginx – ln -s /etc/nginx/sites-available/website.tld /etc/nginx/sites-enabled/website.tld && /etc/init.d/nginx restart – we’re ready to install certbot.

root@proxy:~# apt-add-repository ppa:certbot/certbot ; apt update ; apt install -y python-certbot-nginx
                [[[ output elided ]]]

Now that certbot’s installed, we just need to run it once and let it automatically configure. Note that I chose to have Certbot automatically configure nginx to force-redirect all HTTP traffic to HTTPS for me. (And don’t judge me for not saying yes to giving the email address to the EFF: that’s because I’m already on the mailinglist, and a dues-paid-up member!)

root@proxy:~# certbot --nginx

Saving debug log to /var/log/letsencrypt/letsencrypt.log
Plugins selected: Authenticator nginx, Installer nginx
Enter email address (used for urgent renewal and security notices) (Enter 'c' to cancel): you@website.tld

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Please read the Terms of Service at You must agree in order to register with the ACME server at
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(A)gree/(C)ancel: A

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Would you be willing to share your email address with the Electronic Frontier Foundation, a founding partner of the Let's Encrypt project and the non-profit organization that develops Certbot? We'd like to send you email about our work encrypting the web, EFF news, campaigns, and ways to support digital freedom.
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(Y)es/(N)o: N

Which names would you like to activate HTTPS for?
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1: website.tld
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Select the appropriate numbers separated by commas and/or spaces, or leave input
blank to select all options shown (Enter 'c' to cancel): 
Obtaining a new certificate
Performing the following challenges:
http-01 challenge for website.tld
http-01 challenge for
Waiting for verification...
Cleaning up challenges
Deploying Certificate to VirtualHost /etc/nginx/sites-enabled/website.tld
Deploying Certificate to VirtualHost /etc/nginx/sites-enabled/website.tld

Please choose whether or not to redirect HTTP traffic to HTTPS, removing HTTP access.
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1: No redirect - Make no further changes to the webserver configuration.
2: Redirect - Make all requests redirect to secure HTTPS access. Choose this for new sites, or if you're confident your site works on HTTPS. You can undo this change by editing your web server's configuration.
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Select the appropriate number [1-2] then [enter] (press 'c' to cancel): 2
Redirecting all traffic on port 80 to ssl in /etc/nginx/sites-enabled/website.tld
Redirecting all traffic on port 80 to ssl in /etc/nginx/sites-enabled/website.tld

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Congratulations! You have successfully enabled https://website.tld and

You should test your configuration at:
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 - Congratulations! Your certificate and chain have been saved at:
 Your key file has been saved at:
 Your cert will expire on 2019-03-22. To obtain a new or tweaked
 version of this certificate in the future, simply run certbot again
 with the "certonly" option. To non-interactively renew *all* of
 your certificates, run "certbot renew"
 - Your account credentials have been saved in your Certbot
 configuration directory at /etc/letsencrypt. You should make a
 secure backup of this folder now. This configuration directory will
 also contain certificates and private keys obtained by Certbot so
 making regular backups of this folder is ideal.
 - If you like Certbot, please consider supporting our work by:

Donating to ISRG / Let's Encrypt:
 Donating to EFF:

That’s it. You should test the renewal process once using certbot renew --dry-run, and make sure it works (it should; mine certainly did). There’s already a cron job created for you in /etc/cron.d, so you don’t need to do anything else – you’ve got working SSL on your reverse proxy server now.

Apache 2.4 / Ubuntu Trusty problems

Found out the hard way today that there’ve been SIGNIFICANT changes in configuration syntax and requirements since Apache 2.2, when I tried to set up a VERY simple couple of vhosts on Apache 2.4.7 on a brand new Ubuntu Trusty Tahr install.

First – the a2ensite/a2dissite scripts refuse to work unless your vhost config files end in .conf. BE WARNED. Example:

you@trusty:~$ ls /etc/apache2/sites-available
you@trusty:~$ sudo a2ensite testsite.tld
ERROR: Site testsite.tld does not exist!

The solution is a little annoying; you MUST end the filename of your vhost configs in .conf – after that, a2ensite and a2dissite work as you’d expect.

you@trusty:~$ sudo mv /etc/apache2/sites-available/testsite.tld /etc/apache2/sites-available/testsite.tld.conf
you@trusty:~$ sudo a2ensite testsite.tld
Enabling site testsite.tld
To activate the new configuration, you need to run:
  service apache2 reload

After that, I had a more serious problem. The “site” I was trying to enable was nothing other than a simple exposure of a directory (a local ubuntu mirror I had set up) – no php, no cgi, nothing fancy at all. Here was my vhost config file:

<VirtualHost *:80>
        ServerAlias us.archive.ubuntu.local 
        Options Includes FollowSymLinks MultiViews Indexes
        DocumentRoot /data/apt-mirror/mirror/
	*lt;Directory /data/apt-mirror/mirror/>
	        Options Indexes FollowSymLinks
	        AllowOverride None

Can’t get much simpler, right? This would have worked fine in any previous version of Apache, but not in Apache 2.4.7, the version supplied with Trusty Tahr 14.04 LTS.

Every attempt to browse the directory gave me a 403 Forbidden error, which confused me to no end, since the directories were chmod 755 and chgrp www-data. Checking Apache’s error log gave me pages on pages of lines like this:

[Mon Jun 02 10:45:19.948537 2014] [authz_core:error] [pid 27287:tid 140152894646016] [client] AH01630: client denied by server configuration: /data/apt-mirror/mirror/

What I eventually discovered was that since 2.4, Apache not only requires explicit authentication setup and permission for every directory to be browsed, the syntax has changed as well. The old “Order Deny, Allow” and “Allow from all” won’t cut it – you now need “Require all granted”. Here is my final working vhost .conf file:

<VirtualHost *:80>
        ServerAlias us.archive.ubuntu.local 
        Options Includes FollowSymLinks MultiViews Indexes
        DocumentRoot /data/apt-mirror/mirror/
	<Directory /data/apt-mirror/mirror/>
	        Options Indexes FollowSymLinks
	        AllowOverride None
                Require all granted

Hope this helps someone else – this was a frustrating start to the morning for me.

Heartbleed SSL vulnerability

Last night (2014 Apr 7) a massive security vulnerability was publicly disclosed in OpenSSL, the library that encrypts most of the world’s sensitive traffic. The bug in question is approximately two years old – systems older than 2012 are not vulnerable – and affects the TLS “heartbeat” function, which is why the vulnerability has been nicknamed HeartBleed.

The bug allows a malicious remote user to scan arbitrary 64K chunks of the affected server’s memory. This can disclose any and ALL information in that affected server’s memory, including SSL private keys, usernames and passwords of ANY running service accepting logins, and more. Nobody knows if the vulnerability was known or exploited in the wild prior to its public disclosure last night.

If you are an end user:

You will need to change any passwords you use online unless you are absolutely sure that the servers you used them on were not vulnerable. If you are not a HIGHLY experienced admin or developer, you absolutely should NOT assume that sites and servers you use were not vulnerable. They almost certainly were. If you are a highly experienced ops or dev person… you still absolutely should not assume that, but hey, it’s your rope, do what you want with it.

Note that most sites and servers are not yet patched, meaning that changing your password right now will only expose that password as well. If you have not received any notification directly from the site or server in question, you may try a scanner like the one at to see if your site/server has been patched. Note that this script is not bulletproof, and in fact it’s less than 24 hours old as of the time of this writing, up on a free site, and under massive load.

The most important thing for end users to understand: You must not, must not, MUST NOT reuse passwords between sites. If you have been using one or two passwords for every site and service you access – your email, forums you post on, Facebook, Twitter, chat, YouTube, whatever – you are now compromised everywhere and will continue to be compromised everywhere until ALL sites are patched. Further, this will by no means be the last time a site is compromised. Criminals can and absolutely DO test compromised credentials from one site on other sites and reuse them elsewhere when they work! You absolutely MUST use different passwords – and I don’t just mean tacking a “2” on the end instead of a “1”, or similar cheats – on different sites if you care at all about your online presence, the money and accounts attached to your online presence, etc.

If you are a sysadmin, ops person, dev, etc:

Any systems, sites, services, or code that you are responsible for needs to be checked for links against OpenSSL versions 1.0.1 through 1.0.1f. Note, that’s the OpenSSL vendor versioning system – your individual distribution, if you are using repo versions like a sane person, may have different numbering schemes. (For example, Ubuntu is vulnerable from 1.0.1-0 through 1.0.1-4ubuntu5.11.)

Examples of affected services: HTTPS, IMAPS, POP3S, SMTPS, OpenVPN. Fabulously enough, for once OpenSSH is not affected, even in versions linking to the affected OpenSSL library, since OpenSSH did not use the Heartbeat function. If you are a developer and are concerned about code that you wrote, the key here is whether your code exposed access to the Heartbeat function of OpenSSL. If it was possible for an attacker to access the TLS heartbeat functionality, your code was vulnerable. If it was absolutely not possible to check an SSL heartbeat through your application, then your application was not vulnerable even if it linked to the vulnerable OpenSSL library.

In contrast, please realize that just because your service passed an automated scanner like the one linked above doesn’t mean it was safe. Most of those scanners do not test services that use STARTTLS instead of being TLS-encrypted from the get-go, but services using STARTTLS are absolutely still affected. Similarly, none of the scanners I’ve seen will test UDP services – but UDP services are affected. In short, if you as a developer don’t absolutely know that you weren’t exposing access to the TLS heartbeat function, then you should assume that your OpenSSL-using application or service was/is exploitable until your libraries are brought up to date.

You need to update all copies of the OpenSSL library to 1.0.1g or later (or your distribution’s equivalent), both dynamically AND statically linked (PS: stop using static links, for exactly things like this!), and restart any affected services. You should also, unfortunately, consider any and all credentials, passwords, certificates, keys, etc. that were used on any vulnerable servers, whether directly related to SSL or not, as compromised and regenerate them. The Heartbleed bug allowed scanning ALL memory on any affected server and thus could be used by a sufficiently skilled user to extract ANY sensitive data held in server RAM. As a trivial example, as of today (2014-Apr-08) users at the Ars Technica forums are logging on as other users using password credentials held in server RAM, as exposed by standard exploit test scripts publicly disclosed.

Completely eradicating all potential vulnerability is a STAGGERING amount of work and will involve a lot of user disruption. When estimating your paranoia level, please do remember that the bug itself has been in the wild since 2012 – the public disclosure was not until 2014-Apr-07, but we have no way of knowing how long private, possibly criminal entities have been aware of and/or exploiting the bug in the wild.

Enabling core dumps on Apache2.2 on Debian

It was quite an adventure today, figuring out how to get a segfaulting Apache to give me core dumps to analyze on Debian Squeeze. What SHOULD have been easy… wasn’t. Here’s what all you must do:

First of all, you’ll need to set ulimit -c unlimited in your /etc/init.d/apache2 script’s start section.

case $1 in
log_daemon_msg "Starting web server" "apache2"
# set ulimit for debugging
# ulimit -c unlimited

Now make a directory for core dumps – mkdir /tmp/apache2-dumps ; chmod 777 /tmp/apache2-dumps – then you’ll need to apt-get install apache2-dbg libapr1-dbg libaprutil1-dbg

And, the current (Debian Squeeze, in May 2012) version of Debian does not have PIE support in the default gdb, so you’ll need to install gdb from backports. So, add deb squeeze-backports main to /etc/apt/sources.list, then apt-get update && apt-get install -t squeeze-backports gdb

Now add “CoreDumpDirectory /tmp/apache2-dumps” to /etc/apache2/apache2.conf (or its own file in conf.d, whatever), then /etc/init.d/apache2 stop ; /etc/init.d/apache2 start

And once you start getting segfaults, you’ll get a core in /tmp/apache2-dumps/core.

Finally, now that you have your core, you can gdb apache2 /tmp/apache2-dumps/core, bt full, and debug to your heart’s content. WHEW.