Geek Guide: Apache Web Servers and SSL Authentication

GEEK GUIDE  APACHE WEB SERVERS AND SSL AUTHENTICATION
2
About the Sponsor�� 4
Overview�� 5
Introduction to SSL/TLS�� 7
Types of Certificates�� 10
Certificate Authorities�� 13
Getting Ready for SSL/TLS�� 15
Installing the Certificate�� 19
Conclusion�� 24
Resources�� 25
Table of Contents
REUVEN M. LERNER is a Web developer, consultant, trainer and longtime columnist
for Linux Journal. He recently completed his PhD in Learning Sciences from Northwestern
University. You can read his blog, Twitter feed and newsletter at http://lerner.co.il.
Reuven lives with his wife and three children in Modi’in, Israel.

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About the Sponsor
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Overview
Congratulations! You’ve decided to set up a Web site.
The site might be for your personal use, for sharing family
pictures, for a blog, for an SaaS application, or any number
of other possibilities. In all of those cases, people will access
your site using the Hypertext Transfer Protocol (HTTP). HTTP
has evolved and improved through the years, but one thing
about it hasn’t changed—the fact that all of the traffic sent
Apache
Web Servers
and SSL
Authentication
REUVEN M. LERNER

6
on an HTTP connection is unencrypted.
If you’re running a personal site, this doesn’t really
matter. But if and when you’re interested in doing
something a bit more exciting, you might well want or need
to add encryption to your server. Encrypted HTTP is known
as HTTPS, and it involves the addition of SSL/TLS encryption
to the HTTP protocol. In order for your site to handle
encrypted connections, you need to install and configure an
SSL certificate. This Geek Guide is here to help you through
that process, making it easy for you to move an existing site
using HTTP into one using HTTPS.
There are several motivations for using HTTPS, rather than
HTTP, on Web sites. One is that a growing number of sites
are engaging in commerce, and many payment providers
(and their security standards, known as PCI) are requiring
that commercial sites not only encrypt traffic having to do
with payments, but also with logins and other aspects.
In some cases, sites are either required to keep
information as private as possible, or they wish to do so
in order to avoid regulatory problems. Medical and legal
offices, for example, would want to avoid having others
eavesdrop on discussions employees are having and e-mail
messages they are sending and receiving. Without a secure
channel, it might be possible for someone to listen in,
without actually gaining access to the network.
Some users may be more likely to trust a site that is
encrypting traffic. Thus, some sites use HTTPS not because
they need to do so, but because they know users might feel
more comfortable with an HTTPS connection in place.

7
Finally, some people say that given how inexpensive
and easy it is to use SSL, and to use an encrypted version
of HTTP, that they might as well do so. Gone are the
days when running an HTTPS server was difficult,
time-consuming or too CPU-intensive for a server;
today’s computers are more than powerful enough to
handle HTTPS traffic.
The bottom line is that whether you want or need to do
so, adding HTTPS to a site you’re running isn’t very hard
to do. In this Geek Guide, I walk through what SSL/TLS is
(and isn’t), how you can create or buy a certificate, how
to install that certificate into an Apache server and then
how to configure Apache such that a subset of URLs on
your system are covered by SSL.
Introduction to SSL/TLS
First, it’s important to understand some terminology and
technology. HTTPS differs from plain-old HTTP in that it is
“secure”. However, people often are surprised to discover
that this means the connection between the users’ browsers
Gone are the days when running an HTTPS
server was difficult, time-consuming or
too CPU-intensive for a server; today’s
computers are more than powerful enough
to handle HTTPS traffic.

8
and the server is secure. It doesn’t guarantee anything
about the security of the server or of their data. All that
HTTPS ensures is that if you’re using a café’s Wi-Fi to
purchase something on Amazon, no one will be able
to read your user name and password as they are sent to
Amazon’s login system.
The security in HTTPS uses a protocol known as transport
layer security, or TLS for short. The current stable version of
TLS is 1.2, with version 1.3 currently in draft form. Although
TLS has been around since 1999, and replaced the earlier
SSL (secure socket layer) protocol invented by Netscape,
many people continue to refer to the protocol as SSL, even
though currently no version of SSL is considered to be
secure. Thus, when people mention an SSL certificate, they
almost certainly actually are referring to a TLS certificate.
The naming difference, it would seem, had little to do with
substantial changes to the protocols and was more political
than technical in nature.
It doesn’t help that the best-known open-source
library for working with TLS is still known as OpenSSL.
You can read more about the OpenSSL library at its Web
site: http://openssl.org.
TLS (and SSL) use public-key cryptography to ensure that
communication between a user’s browser and a Web server
is kept secure. In public-key cryptography, each party has
two keys, one public and one private. The public key (as its
name implies) can be shared freely with the world, while
the private key (as its name implies) must be kept secret.
The two keys are inverses of each other, allowing you to use

9
them in two different ways. You can encrypt text and ensure
that only a specific person can read it, using that person’s
public key. Only by using the private key can the user then
decrypt the information. You also can use the keys to sign
documents digitally. Encrypt a document using your private
key, and everyone can decrypt the document, but they also
will know that you, and only you, could have signed it.
You can imagine, given this description, that you can
use these keys to ensure that traffic between a browser
and server are encrypted and, thus, unreadable to anyone
without the appropriate keys. A site could, in theory,
distribute its public key to anyone and everyone. A browser
then could use the public key to encrypt HTTP traffic. Only
the site would be able to read that traffic, because only it
would have the private key.
However, things in the TLS world are a bit more complex
than that. For starters, remember that you need to have
bidirectional encryption, handling not only requests sent to
the server, but also responses sent to the browser. Add to
that fact the logistical aspect of distributing a server’s public
keys in order for a browser to connect with HTTPS. And
then you also have the issue of ensuring that the key you
receive is a genuine one, and not the result of a “man in
the middle” attack.
The bidirectional part of TLS is perhaps easiest to explain:
the actual public and private keys aren’t directly used to
encrypt the traffic. Rather, they’re used to create a “session
key” (that is, an encryption key that is used for a single
client-server session), and to exchange it securely.

10
Distributing the server’s keys in a reasonable way is
a bit trickier. After all, if I go to a server, how does my
browser know if the server’s public key (distributed in
a document known as a “certificate”, along with some
other data) is genuine or the result of someone having
broken into the server?
The answer is that the server’s public key is digitally
signed, as described above, not by the server itself, but
from an organization known as a certificate authority, or
CA. Your browser comes preconfigured with the public
keys of a large number of CAs. Thus, when a server sends
its public key signed by a well known CA, your browser
can guarantee the truth of the signature and then use the
server’s public key as part of its creation of a shared session
key between the browser and server.
Making your Web site secure is thus a matter of creating
a set of certificates (public and private) for your server,
signed by a well known CA. This Geek Guide walks through
the process of doing just that.
Types of Certificates
A certificate contains not only the server’s key, but also
some information about the server to ensure that the
key is legitimate. For example, if I create a certificate
Distributing the server’s keys in a reasonable
way is a bit trickier.

11
for XYZ Corp., I cannot use it on a server run by JKL
Corp. The certificate is issued for a particular hostname,
providing an even greater degree of security and trust.
If you’re going to be securing a single site on a single
domain, you probably can get this simplest type of TLS
certificate. When you create the certificate, you must
describe the location, the organization and the full
hostname of the server in question. Note that the certificate
is based on the hostname and not on the IP address; this
means if you move your server to a new location (but
keep the same name), you likely won’t need to change the
certificate, so long as the hostname remains the same.
However, a growing number of sites cannot use such
simple, single-hostname certificates. The simplest example
of such a case is a Web site with multiple hostnames,
such as “example.com” and “www.example.com”. In such
a case, you would have to purchase and configure two
separate certificates, one for each hostname. Alternatively,
you could buy and configure what’s known as a wildcard
certificate, which allows you to use a single certificate with
a number of hosts within a particular domain. The more
hosts you want to secure under a specific domain, the more
a wildcard certificate will save you time and money.
It’s important to understand that wildcard certificates
are good only for a single domain. Thus, if your company
runs three different on-line stores, each of which with its
own domain, you will need to purchase three separate
certificates. You cannot use a wildcard in that case. In such
a situation, you’ll need to indicate the domain (but not the

12
hostnames) that should be associated with the certificate at
purchase time. The hostname cannot be changed once the
certificate is issued, which means if you aren’t completely
sure about your domain name, it might be wise to wait a bit
before making the purchase.
If you are running three (or more) domains on your server,
and particularly if you think you might need to add more
domains to the same server, you should consider a unified
communications certificate, otherwise known as a UCC.
The name might sound complex, but it isn’t. The basic idea
behind a UCC is that you can add and remove domains from
the certificate during its lifetime. You don’t need to know
the domain names when the certificate is created; you can,
after the certificate has been issued, modify and re-issue it
with the latest hostnames. Each change to the certificate
requires re-installing it on your server, but as you’ll see,
the installation process is quite straightforward and easy.
Each alternative domain name on a certificate is known as a
subject alternative name (SAN), and the number of SANs is
the main hard-coded limit on a UCC.
If you are running three (or more) domains on
your server, and particularly if you think you might
need to add more domains to the same server,
you should consider a unified communications
certificate, otherwise known as a UCC.

13
For example, one of my clients needed a TLS certificate
for a site. However, the site used two different domain
names, and we knew when we ordered the certificate
that we would be adding about ten additional domains
within a year—with an eye toward about 60 total. So,
we bought a UCC that allowed for up to 100 SANs.
Every time we registered a new domain name for the
site, we would re-generate the certificate to include the
new name, and then install this new version. However,
the UCC allowed us to add and remove SANs without
incurring additional costs or the administrative overhead
of working with many different certificates.
Certificate Authorities
Once you have decided what kind of certificate you want
to install, you need to consider the certificate authority
(CA) you want to use. At the end of the day, a CA is
there to guarantee that the certificates it issues are
valid, and that the information the certificates contain
hasn’t been tampered with. As a result, you want to
choose a CA whose certificates have been installed in a
large number of browsers. As a general rule, nearly any
CA vendor will be recognized by your browser, but if
you’re going to purchase from a smaller operation, it’s
probably best to be sure, just in case. It’s true that the
CA’s name is mentioned in the SSL certificate. Thus, if
you go to a Web site and click on the HTTPS logo, you
should be given an option to see the name of the CA
that authorized the certificate.

14
If you use a certificate whose CA isn’t recognized
by all browsers, some users will be presented with a
(rather scary) warning, telling them not to trust this
site’s certificate. In most cases, I have found that such
warnings are because of innocent misconfiguration
of the server. However, I can almost guarantee that
your users will not accept a certificate that produces
such warnings.
However, there are cases in which you don’t want or
need to get a certificate from a CA. For example, if you
just want to set up SSL for an experiment or for your
own development machine, you almost certainly don’t
want to pay money just to get a certificate issued. In
such cases, you can self-sign your certificate.
I should stress that there is no technical barrier to
always self-signing certificates. You could, in theory,
create a multi-billion dollar e-commerce empire
using only self-signed certificates. However, the odds
of being able to do this are slim, because so many
modern browsers will warn users—often with bold, red
warnings that are quite scary to the uninitiated—that
If you use a certificate whose CA isn’t
recognized by all browsers, some users will
be presented with a (rather scary) warning,
telling them not to trust this site’s certificate.

15
they are visiting a site whose certificate is signed by a
CA unknown to the browser. Might the TLS certificate
be legitimate? Yes, but there’s no way to know that
for sure, because the browser doesn’t have any way to
validate the digital signature on the server’s certificate.
So although it’s easy and fast to self-sign a certificate,
you should do so only when you are sure that the
general public won’t be relying on that certificate for
anything that directly affects your business.
Getting Ready for SSL/TLS
This Geek Guide describes how to install an SSL
certificate on your Apache HTTP server. Of course, other
HTTP servers exist. In the past few years, nginx has
become particularly powerful. Apache is not only popular,
but it’s also quite flexible. Indeed, its claim to fame is
that Apache is based on a large number of modules,
any of which can be included or excluded in your server
configuration. This not only allows you to create what’s
effectively a custom HTTP server for your purposes, but it
also (if you’re interested in doing so) offers the option of
writing your own custom modules.
The Apache module that handles SSL/TLS is known
as mod_ssl and is included in the basic Apache
configuration. In order to have a secure server, not only
must you have mod_ssl installed, but it also must be
activated. On many modern Linux distributions, such
as Ubuntu, the Apache configuration directory has a
mods-available subdirectory, as well as a mods-installed

16
subdirectory. Typically, modules are placed inside
mods-available; if you actually want to use a module,
you create a symlink from mods-installed back to
mods-available. On one of my Apache servers, I have
about 30 modules in mods-available, but only about
15 links back to them in mods-installed.
Installing a module means adding two symlinks:
one to a .conf configuration file containing the
modules’ configuration, as well as a .load file,
which typically contains a single Apache LoadModule
directive, telling Apache where the compiled module
is located.
Now, you could create these symlinks yourself. But as
a general rule, it’s easier to let Apache take care of this
for you, using the alias a2enmod command that comes
with many modern Debian-based Linux distros. Thus, to
enable the mod_ssl module on Ubuntu or Debian, you
simply can run:
$ sudo e2enmod ssl
Now that the SSL module is installed, you’ll need
to order or create an SSL certificate. I’m going to
assume here that you’ll be going to your favorite CA
and ordering a certificate. However, before you take
out your wallet and go to the CAs Web site, you’ll first
need to do some work on your server. That’s because a
CA can create a certificate only if it first has received
a “certificate signing request”, known as a CSR. Funny

17
as it might sound, this basically means creating a
certificate (the CSR) that you give to the CA. The
CA uses the CSR to create your SSL certificate. You
then download the actual certificate and install it
on your server.
Given that the entire TLS infrastructure is based on
public and private keys, it won’t surprise you to hear
that you’ll need to generate a pair of keys and then
use those keys to create your CSR. You’ll do this using
the openssl command, which comes with the OpenSSL
library. If you don’t see the openssl command on your
computer, you’ll need to install OpenSSL from your
distribution’s archive.
If this is the first time you’re dealing with any of this,
you’ll need to generate a new keypair, as well as the
CSR itself. Here is the (admittedly long) command you’ll
need to run in order to get this to work:
$ sudo openssl req -new -newkey rsa:2048
➥-nodes -keyout key.pem -out req.pem
Given that the entire TLS infrastructure is
based on public and private keys, it won’t
surprise you to hear that you’ll need to
generate a pair of keys and then use those
keys to create your CSR.

18
Let’s take apart the above command:
n openssl req -new tells the OpenSSL command that
you’re creating a new CSR.
n The -newkey option indicates that you want to generate
a new keypair, rather than use an existing one.
n The rsa:2048 tells the “newkey” option that you want
to generate a 2,048-bit RSA keypair.
n The -nodes option indicates that you don’t want to
encrypt the private key with a passphrase. On the one
hand, this is indeed less secure and means that someone
can restart your Apache server without knowing the
passphrase. On the other hand, do you want to have to
enter the passphrase every time you restart your server?
More security-minded folks than myself, or people
with staff members on duty 24/7 who can take care of
restarting servers, might want to remove this option.
n The -keyout key.pem option tells OpenSSL where it
should store the newly created private key. The output is
in PEM format, which is frequently used with OpenSSL,
which explains the file extension. You can use whatever
filename you want, of course.
n Finally, “-out req.pem” tells OpenSSL where it should
store the CSR that it creates.

19
Once you run the above command, you’ll be prompted
to enter a bunch of details about your server—where
it’s located, the company name and your name and
e-mail address.
At the end of this process, OpenSSL will create the two
files that you requested: key.pem and req.pem.
At this point, you have a CSR. You can use it to request
a TLS certificate from your favorite CA, or you can use it to
self-sign a TLS certificate created on your own machine. If
you use a commercial CA, you’ll submit the CSR and then
you’ll probably have to wait a bit for it to be processed
and approved, and for you to get the certificate. You’ll
likely receive e-mail from your CA, telling you that the
certificate is now available for download.
Installing the Certificate
Although people might make a big deal out of TLS
certificates, the fact is that they’re just files—digitally
signed files maybe, but files nonetheless. Thus, when
you download the certificate from your CA’s Web site,
you’ll have a file that you then must put on your server.
Actually, you’ll likely have to put three files on your
server, one of which you already have:
n The key.pem file, containing the private key from your
server’s keypair.
n The TLS certificate that you received from your CA,
which likely will have a .crt extension.

20
n The “Chain file” from your CA, which is used as part of
the identification process with your CA. This also likely
will have a .crt extension.
On Debian-based systems, these files typically are placed
in /etc/apache2/ssl. I generally put the private key (that is,
the key.pem file) under the “private” subdirectory and the
.crt files in the “certs” subdirectory.
You now have installed your certificate! Moreover, you have
all of the pieces you need in order for it to work. But, you still
haven’t told Apache to activate SSL or to use your certificates.
In order to do that, you’ll need to return to your Apache
configuration. Whereas HTTP typically uses port 80, HTTPS
generally uses port 443. Thus, you’ll probably want to set
up a separate virtual host on port 443, in which you’ll set
up your HTTPS configuration. The config can be as simple
as the following:
VirtualHost *:443
ServerName mydomain.com
DocumentRoot /var/www/www.mydomain.com/
SSLEngine on
SSLOptions +FakeBasicAuth +ExportCertData +StrictRequire
SSLCertificateFile /etc/apache2/ssl/certs/mydomain.com.crt
SSLCertificateKeyFile /etc/apache2/ssl/private/mydomain.key
SSLCertificateChainFile /etc/apache2/ssl/certs/myca.crt
/VirtualHost

21
The above configuration would be for the server at
MyDomain.com; it’s probably safe to assume that you’re
working on a server at a different domain. The file starts
by opening a VirtualHost section, indicating to Apache
that you want to configure this virtual host for requests
to mydomain.com on port 443. Note that if you don’t set
ServerName, you will get errors from Apache.
If you have successfully added the ssl module to
your Apache configuration, as described above, the
SSL* configuration directives should be available and
should work. Using the directives without installing
the module (and then restarting Apache) will result in
error messages, indicating that you are trying to use
undefined directives.
The above configuration uses a number of different
SSL-related directives and options:
n SSLEngine on, as you can imagine, turns on the
SSL system. SSL can be a heavy burden on some
servers (although not nearly as much as it used to
be), and including the module isn’t enough to get
SSL features working.
n As is the case with many Apache modules, mod_ssl
offers a number of options. In the above configuration,
I have activated three: FakeBasicAuth (which allows
you to use standard Apache authentication for user
access), ExportCertData (which passes along several
environment variables having to do with SSL to the Web

22
application) and StrictRequire (which allows you to
force SSL on particular pages).
You then tell mod_ssl where it can find the three files it
needs in order to run SSL successfully:
n SSLCertificateFile points to the certificate that you
received from your CA.
n SSLCertificateKeyFile points to the private key that
you generated earlier with the openssl command.
n SSLCertificateChainFile points to a certificate that
you should have received from your CA.
With all of the above in place, you should be able to
restart your Apache server! Then, assuming that your site is
at MyDomain.com, you can go to https://MyDomain.com/.
If all is configured correctly, then this should answer.
However, now you have a bit of an issue—your site likely
is responding on both HTTP and HTTPS, and might well
be configured differently. It’s common to want to redirect
traffic from your HTTP site to your HTTPS site. In other
It’s common to want to redirect traffic from
your HTTP site to your HTTPS site.

23
words, if I go to http://MyDomain.com/, the site should
redirect me to https://MyDomain.com/. One simple way
to do that is to use the Redirect directive to map an old
URL to a new one. For example, on your HTTP (non-TLS)
site, you could say:
Redirect permanent / https://MyDomain.com/
This will work only for your home page; if you have a
large number of URLs that you want to redirect, it’s not
sufficient. In such a case, you might well need to use
mod_rewrite, which comes with Apache and allows
you to use regular expressions to grab parts of URLs
and redirect people to there. The advantage of the
Redirect directive is that it’s simple to create, and it
allows you to pick and choose the URLs that will be
redirected to HTTPS.
One of the issues that often surprises people when
working with SSL is that it’s a bit harder to debug than
regular HTTP communication, because everything is
encrypted. One of my favorite techniques to see if a
site is working is to telnet to port 80 and issue a
GET / HTTP/1.0 command by hand. Of course, there’s
no way to do that with HTTPS! Instead, you might
well need to use curl, wget or even your browser to
make requests to your server, and then turn up the
logging level on Apache to make sure that everything
you’re doing is logged and can be analyzed. You also
can set, in your Apache configuration (on my system,

24
in mods-available/ssl.conf), the debugging of SSL to a
higher level:
IfModule mod_ssl.c
ErrorLog /var/log/apache2/ssl_engine.log
LogLevel debug
/IfModule
This will ensure that whatever happens in mod_ssl is
logged, and thus can be debugged more easily. Note that the
“debug” log level is rather verbose; you likely will have to
wade through a fair amount of text to find what you want.
However, that’s better than not being able to find anything
useful, which is what the “info” level often ends up doing.
Another problem that people sometimes have is a
mismatch between the server name and the name on
the certificate. When you create the CSR, you must
use the right hostname. You can’t just move it around
willy-nilly. And, if you change the name of your server or
your domain, the SSL certificate no longer will be valid.
Conclusion
SSL (and TLS) used to be big and complex, and difficult for
people to install. Today, making your site secure is often a
necessary part of doing business—either because you must
do it or because you want your customers to trust you. If you
use Apache and Linux, configuring your server to use TLS
isn’t that difficult. The tools are fairly easy to understand and
use, and they come with every installation of Apache.n

25
Perhaps the best guide to Apache and SSL is, not surprisingly,
the documentation on Apache’s own site. The main page on the
subject is at https://httpd.apache.org/docs/2.2/ssl.
If you’re looking for the specific SSL-related directives, you will
need the mod_ssl documentation: https://httpd.apache.org/
docs/2.2/mod/mod_ssl.html.
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