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== link:index.html[Index] -> link:cookbook.html[Cookbook]
Cookbook: SSL, TLS and certificates
This section answers some general questions and details the procedure
to generate SSL keys.
Configure vServer SSL Certificates
To start serving HTTPS traffic from Cherokee you will have to
link:#ssl-support[enable SSL support] and obtain a
link:#free-certificates[signed certificate] (or
link:#self_sign[signed your own]). Ensure that the certificate files
have the appropriate permissions for your OS and that you know the locations
of the following:
. Signed Certificate file
. Private Key file used to generate CSR for the above
. CA List or Chain file (Optional, depending on signing authority of your certificate)
All files should be generated using PEM-encoding.
Certificates are configured at the vServer level in the *Security* tab. *This
means you must have a vServer setup that corresponds to your Certificate's
security scope*. Enter the full paths for your Certificate and corresponding Private
Key file. To add a certificate chain file to you CA List set *Client Certs. Request*
to _Accept_ then put the full path to your chain file in the _CA List_ box.
image::media/images/admin_vserver_security_ssl.png[Virtual Server - Security]
General questions
.Can the same server provide HTTP and HTTPS?
Yes. HTTP and HTTPS use different server ports. The former binds to
port 80 and the latter to port 443, so there is no conflict between
them. To provide HTTPS you will need matching certificates.
Keep in mind that to have one of your virtual servers with HTTPS
enabled you will need to configure HTTPS settings for all of them.
.Which port does HTTPS use?
HTTPS can run on any port, but the standards specify port 443. That's
where any HTTPS compliant browser will look by default. You can change
that by specifying another port in the URL. For example, would look for an HTTPS server on port 8080.
.Can one host handle HTTPS requests for multiple virtual servers?
Yes, it can. This is a common question because a web server cannot see
the hostname header when the HTTPS request is being processed. The
user entered host part of the URI must match the Common Name (CN)
provided by the certificate. Since virtual hosts are in use, the CN of
the first available certificate may or may not match the one specified
in the early stages of TLS negotiation.
Fortunately this can be overcomed by using SNI (Server Name
Indication), which places the host information in the SSL
handshake. If the web server is accessed through a web browser that
supports SNI, things will just work. Every modern web browser does.
For legacy scenarios where using SNI if not possible, there is a
workaround detailed in the next question.
.Are there workarounds when SNI can't be used?
Using SNI is the clean and standard way to go. For legacy scenarios
where using SNI is not and option, Cherokee supports a workaround.
The mechanism requires the web server to listen to several IPs, and to
assign a specific one for each virtual server. This can be done
through the `Match` tab of the virtual server configuration, by
assigning an IP-method to the desired IP. Remember that the list of
virtual servers is evaluated from top to bottom, so in case you
specify the same IP for several virtual servers, only the first one
will actually match. In case you need more flexibility than that to
match your domains, you can always add more than one matching criteria
on that section. An IP/Subnet match plus a simultaneous wildcard match
is a combination likely to cover every corner-case scenario you are
presented with.
.Can clients be forced to use HTTPS?
After enabling HTTP Strict Transport Security per Virtual Server, a client
gets automatically redirected to HTTPS upon connection to HTTP. In principle
this equals to the match rule "Is TLS/SSL" with an external redirection.
Additionally HSTS adds the HTTP Header "Strict-Transport-Security" to a
secure connection which informs the browser that all other content on
the page must be accessed over HTTPS. The max-age options defines when the
browser can check HTTP again.
.How to enable the SSL support?
SSL support is not enabled by default. You will have to perform three
straightforward actions is order to enable it:
. The first step is to enable a TLS/SSL engine. The option is
located in the link:config_general.html[General] configuration
setting. Cherokee is shipped with a libssl plug-in.
. Once the engine is configured, a new
link:config_general.html#ports_to_listen[binding port] must be
configured. By default, HTTPS uses the port 443. Remember to add
this port, and to check the TLS toggle button.
. The next step would be to assign SSL certificates to the virtual
servers, starting with the default virtual server. Cherokee uses
SNI to distinguish between virtual servers. The certificate
specified in the default server will be used in the first
negotiation. If not present, the startup sequence will fail. The
configuration is found inside each
link:config_virtual_servers.html#security[virtual server]
configuration, under the Security tab. Only two fields are
required for this to work: `Certificate` (the certificate itself,
which contains the public key and other data and is fed out to
clients to initiate a secure session), and `Certificate key` (the
private key that should be protected at all costs from anyone
gaining access to it). Your mileage may vary, but assuming you are
using a self generated certificate created with the script
provided with Cherokee (more on this later on this same document),
you would have two files, 'cakey.pem' and cakey.key'. Just
provide the full path to 'cakey.pem' for `Certificate`, and
'cakey.key' for `Certificate key`.
. This last step applies only if your certificate is not recognised
by the root CA and you don't want your visitors to manually have
to accept a security exception so that your certificate can be
validated. To correctly address this situation you need a
CA-signed certificate. Furthermore, computers will trust the root
CA, but don't normally know about the intermediate CA that
actually signed your certificates, so you will need an
intermediate file which links such CA to a higher-level CA that
works with all browsers and operating systems. You'll need a
chained certificate file in order to instruct your visitors on how
to follow the chain of trust. You can reed more about
link:#chained-certificates[chained certificates] later on this
document. You will only have to concatenate the certificate files
and put the combined text into a file used for the the
`Certificate` field. This part is _very important_: you have to
concatenate your certificates into a single file in order to use
them in Cherokee. The order in which you concatenate the files is
important. Just issue the following command and you should be
ready to go:
cat public.pem inter_ca_public.pem > chained.pem
.Advanced options
In other te make SSL more secure, Cherokee offers the following advanced
. The `Ciphers` field can be set up to to allow specific cipher suites,
making communication with the client bound to stronger ciphers.
A good choice might be:
. By default SSL communication prefers the cipher suite preference by
the client. You may understand that if a client prefers a weak cipher
but supports a strong cipher, the strong cipher would never be used.
We have introduced the option `Server Preference` to enforce our
preference on the client. Setting a specific order is possible using
the `Ciphers` field.
.I get certificate errors when having more than one. Workarounds?
This is a scenario known to happen only with some web browsers running
specific Operating Systems. Specifically, there was a report where the
server was using 2 domains, 2 IPs, and 2 SSL Certificates on one
server. Everything worked as expected with Firefox, Opera, and
Chromium, but IE/Chrome on Windows kept showing a certificate error
on the domain that was not configured as default.
The workaround consists on creating a dummy default host with the
second IP and certificate. The affected web browsers will then fall
back to the IP and send the correct certificate.
.How to manually test HTTP/HTTPS?
HTTP can easily be tested like this:
$ telnet localhost 80
GET / HTTP/1.0
For HTTPS it is not so easy because of the SSL protocol between TCP
and HTTP. However you can do a similar check with the help of
OpenSSL's s_client command.
$ openssl s_client -connect localhost:443 -state -debug
GET / HTTP/1.0
You will receive detailed information about the SSL handshake before
the actual HTTP response.
A more general command line client is probably a better choice.
link:[cURL] deals with both HTTP and HTTPS, and
performs a bunch of other interesting stuff.
$ curl http://localhost/
$ curl https://localhost/
Private keys and Certificates overview
First some terminology:
. RSA private key file: a digital file that can be used to decrypt
messages sent to you. It has a public component that must be
distributed (via your Certificate file) to allow people to encrypt
those messages.
. CSR, or Certificate Signing Request: a digital file containing your
public key and your name. It is sent to a Certifying Authority (CA)
that will sign it to convert it into a real Certificate.
. Certificate: contains your RSA public key and name, the name of the
CA, and is digitally signed by the CA. A browser that knows the CA
can verify the signature and obtain your RSA public key, which can
be used to send messages which only you can decrypt.
.Does the startup between a non-SSL and an SSL-aware web server differ?
Yes. Although in essence it is exactly the same, if you have a
passphrase on your SSL private key file, a startup dialog will asks
you to enter it. This can be problematic if the web server needs to be
started automatically. In this case, the link:#passphrase[passphrase]
can be removed from your private key at the cost of erasing a security
layer, which brings additional security risks.
.Does Cherokee offer any help for Certificate Generation?
Yes. A script is provided to assist you with Certificate Generation.
Just locate the `contrib` subdirectory and type:
And follow the instructions. It will generate the required files, but
you will have to install them manually.
It has been tested and has worked fine every time, but if you don't find
the script or it doesn't work for you can always follow the rest of
the procedure described in this recipe to manually generate the
Locate or
* On Debian or Ubuntu those are usually located under /usr/lib/ssl/misc/
* On MacOS X, you will find them in /System/Library/OpenSSL/misc/
In any other case ``find / -iname -print`` will help you to locate it.
Create a new CA
$ /usr/lib/ssl/misc/ -newca
CA certificate filename (or enter to create) <press enter>
Making CA certificate ...
Generating a 1024 bit RSA private key
writing new private key to './demoCA/private/cakey.pem'
Enter PEM pass phrase: <type the secret phrase again>
Verifying - Enter PEM pass phrase: <type the secret phrase again>
You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
Country Name (2 letter code) [AU]:ES
State or Province Name (full name) [Some-State]:.
Locality Name (eg, city) []:.
Organization Name (eg, company) [Internet Widgits Pty Ltd]:Cherokee Team
Organizational Unit Name (eg, section) []:<Enter>
Common Name (eg, YOUR name) []:Cherokee Certificate Master
Email Address []
Generate a certificate request
$ /usr/lib/ssl/misc/ -newreq
Generating a 1024 bit RSA private key
writing new private key to 'newreq.pem'
Enter PEM pass phrase: <another phrase>
Verifying - Enter PEM pass phrase: <repeat it>
You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
Country Name (2 letter code) [AU]:ES
State or Province Name (full name) [Some-State]:.
Locality Name (eg, city) []:.
Organization Name (eg, company) [Internet Widgits Pty Ltd]:Cherokee web server
Organizational Unit Name (eg, section) []:.
Common Name (eg, YOUR name) []
Email Address []
Please enter the following 'extra' attributes
to be sent with your certificate request
A challenge password []: <Enter>
An optional company name []: <Enter>
Request (and private key) is in newreq.pem
Sign the certificate request
$ /usr/lib/ssl/misc/ -sign:
Using configuration from /usr/lib/ssl/openssl.cnf
Enter pass phrase for ./demoCA/private/cakey.pem:
Check that the request matches the signature
Signature ok
Certificate Details:
Serial Number: 1 (0x1)
Not Before: Aug 17 13:12:44 2003 GMT
Not After : Aug 16 13:12:44 2004 GMT
countryName = ES
organizationName = Cherokee web server
commonName =
emailAddress =
X509v3 extensions:
X509v3 Basic Constraints:
Netscape Comment:
OpenSSL Generated Certificate
X509v3 Subject Key Identifier:
X509v3 Authority Key Identifier:
DirName:/C=ES/ST=Madrid/L=Madrid/O=Cherokee Team/CN=Cherokee Certificate Master/
Certificate is to be certified until Aug 16 13:12:44 2004 GMT (365 days)
Sign the certificate? [y/n]:y
1 out of 1 certificate requests certified, commit? [y/n]y
Write out database with 1 new entries
Data Base Updated
Signed certificate is in newcert.pem
Self signed certificates
It is another way to generate certificate files. Ramon Pons sent this
little script to create self signed certificates::
openssl req -days 1000 -new -x509 -nodes -out $CERTNAME -keyout $CERTNAME
chmod 600 $CERTNAME
openssl verify $CERTNAME
if [ $? != 0 ]; then
\mv $CERTNAME $CERTNAME.not_valid
You can see that, in essence, it issues the following command:
$ openssl req -new -x509 -nodes -out server.crt -keyout server.key
Which would produce a couple of files: the SSL Certificate File
(server.crt) and the SSL Certificate key file (server.key).
This server.key does not have any passphrase. To add a passphrase to
the key, you should run the following command, and enter & verify the
passphrase as requested.
$ openssl rsa -des3 -in server.key -out
$ mv server.key
You should probably backup the key file and the entered passphrase in
a secure location.
Pass-phrase issues
As noted above, if you have a pass-phrase on your SSL private key file,
the web-server start up will remain on hold until you enter it. Here
is the information needed to change it or even remove it, but bare in
mind the security implications.
.How to change the pass-phrase on a private key file?
Simply read it with the old pass-phrase and write it again, specifying
a new pass-phrase. This can be done withe these commands:
$ openssl rsa -des3 -in server.key -out
$ mv server.key
.How to get rid of the pass-phrase?
The RSA private key inside the server.key file is stored in encrypted
format for security reasons. The pass-phrase is needed to decrypt this
file, so it can be read and parsed. Thus, removing it removes a layer
of security from the web server. It is advised to keep a backup copy
of the original file before proceeding.
$ cp server.key
$ openssl rsa -in -out server.key
$ chmod 400 server.key
Since the server.key now contains an unencrypted copy of the key, if
anyone gets it they will be able to impersonate you on the net.
Verifying that a private key matches its Certificate
To view the Certificate and the key run the commands:
$ openssl x509 -noout -text -in server.crt
$ openssl rsa -noout -text -in server.key
The `modulus` and the `public exponent` portions in the key and the
Certificate must match. It is difficult to visually check that the
long modulus numbers are the same, so this approach can be used
instead to obtain the numbers to compare (though it is mathematically
less rigorous).
$ openssl x509 -noout -modulus -in server.crt | openssl md5
$ openssl rsa -noout -modulus -in server.key | openssl md5
To check to which key or certificate a particular CSR belongs you can
perform the same calculation on the CSR as follows:
$ openssl req -noout -modulus -in server.csr | openssl md5
Free signed SSL/TLS certificates
Most services will require a fee to provide you with signed
certificates, but some services will do this for free on their
entry-product line.
You need to make sure that whoever signs your certificate is trusted
as root CA on your operating system of choice. One such service that
works by default on Windows, Linux, and Mac is
link:[StartSSL] is one such service, although there
are probably others out there.
References on getting a free signed cert used while testing the documentation:
Chained SSL certificates
If your public certificate is signed by a Certificate Authority's
intermediate certificate rather than a root certificate, you will need
a chained CA. This is basically a list or path of certificates to
instruct your visitors on how to follow the chain of trust. The list
contains certificates that form the certificate chain (from the
client/server certificate to the root CA certificate).
When using SSL, even a signed certificate can be worthless by
itself. This is because the system will trust the root CA, but won't
normally know about the intermediate CA that actually signed your
Where to go next while following this chain of trust is specified in
the chained certificate. The mechanism by which the certificate chain
works is actually not that complex. When an unrecognized certificate
is received, the certificate chain is used to obtain the root CA
certificate. This chain is a list of certificates used to authenticate
an entity. The path begins with the certificate of that entity, and
each certificate in the chain is signed by the entity identified by
the next certificate in the chain. The chain terminates with a root CA
certificate, that is always signed by the CA itself. The signature of
every certificate in the chain must be verified, all the way from the
certificate owner until the root CA certificate is reached.
To create a certificate chain file, you simply need to your public
certificate and your Certificate Authority's intermediate certificate
together. Assuming your public certificate is `public.pem` (the
certificate that was signed by the Certificate Authority), and your
CA's public certificate (the intermediate Certificate supplied by your
Certificate Authority) is `inter_ca_public.pem`, simply appending both
will suffice to create a valid chained certificate.
cat public.pem inter_ca_public.pem > chained.pem