TDS Tutorial: Tomcat and TDS Security

Best practices and recommendations on securing a production TDS/Tomcat server.

Why Is This Important?

Be afraid

Misconfiguration of Tomcat can introduce vulnerabilities in security.
The following recommendations should be considered "layers" of security: not completely effective by themselves, but more potent when combined.
This is not a complete laundry list of security fixes! Please use it as a starting point when securing your server.
Suggestions below listed in random order (section ordering is not a representation of the section importance).

Keeping Software Versions Up-To-Date

Rationale

Running the most current versions of software keeps your environment protected against known security vulnerabilities. This includes the JDK, Tomcat, the TDS and any other third-party libraries or software you run.
Stay Informed! Subscribe to announcement lists for Tomcat, the TDS and any other software you deploy, to stay abreast of new versions released due to security issues.
As soon as a security issue is disclosed, potential attackers will begin trying to exploit that vulnerability. It is important that you upgrade your software before an attacker uses the vulnerability against you.

Resources

Tomcat security reports
A complete list of known and documented security vulnerabilities associated with each Tomcat release.
tomcat-users mailing list
A high-traffic mailing list made up of Tomcat users. New releases of Tomcat are likely to be announced here.
Java SE Security
Sun's Java security page which includes a chronology of Java security issues and user forums.
thredds mailing list
The THREDDS mailing list where announcements of new releases will be made.
Buqtraq vunerability database
SecurityFocus' database of all known vulnerabilities for all different types of software from different vendors.

Tomcat Process User/Group and $CATALINA_HOME Permissions

Rationale

Background info

The JVM doesn't fork at all, nor does it support setuid() calls. The JVM (and therefore Tomcat) is one process. The JVM is a virtual machine with many threads under the same process.

Because of OS constraints, all threads in the same JVM process must run under the same user id. No thread may run as the root user unless they are all are run as the root user. Hence, any programs run in Tomcat (TDS, manager application, other JSPs and servlets) will run as the root user.
If you choose to run the Tomcat process as the root user, and an attacker manages to exploit a weakness in Tomcat or something running in webapps/ to run arbitrary commands, those commands will be run as the superuser!
We strongly discourage running Tomcat as the root user and recommend creating an unprivileged, dedicated user and group for running the Tomcat process.
We also recommend restricting the permissions of the Tomcat user/group within $CATALINA_HOME.

Creating a dedicated Tomcat user/group & setting permissions in `$CATALINA_HOME`

Create a dedicated user and group for running Tomcat.

In this example, both the user and group names will be names tomcat, and the user's home directory, aka $CATALINA_HOME, is /opt/tomcat (notice the symlink below). The groupadd and useradd commands were run as the root:

# groupadd tomcat
# useradd -g tomcat -d /opt/tomcat tomcat
# passwd tomcat

Tighten the permissions in $CATALINA_HOME

Change the user/group ownership $CATALINA_HOME to the tomcat user and tomcat group:

# cd /opt
# chown -R tomcat:tomcat apache-tomcat-6.0.32
# ls -ld  *tomcat*
drwxr-xr-x  9 tomcat  tomcat  4096 Jul 15 16:03 apache-tomcat-6.0.32
lrwxrwxrwx  1 root    other     20 Jul 15 19:00 tomcat -> apache-tomcat-6.0.32

Change the user/ownership of the $CATALINA_HOME/conf directory to be owned by the root user, have a group of tomcat and have a permission of user/group read only:

# cd /opt/tomcat
# ls -l
total 92
drwxr-xr-x 2 tomcat  tomcat  4096 Jul 15 16:05 bin
drwxr-xr-x 2 tomcat  tomcat  4096 Jul 18 12:18 conf
drwxr-xr-x 2 tomcat  tomcat  4096 Jul 15 16:03 lib
drwxr-xr-x 2 tomcat  tomcat  4096 Feb  2 12:04 logs
drwxr-xr-x 2 tomcat  tomcat  4096 Jul 15 16:03 temp
drwxr-xr-x 7 tomcat  tomcat  4096 Jul 15 16:04 webapps
drwxr-xr-x 2 tomcat  tomcat  4096 Feb  2 12:04 work

# chown -R root:tomcat conf
# chmod -R 440 conf/*
# ls -l conf
total 92
-r--r----- 1 root    tomcat  9978 Feb  2 12:06 catalina.policy
-r--r----- 1 root    tomcat  3713 Feb  2 12:06 catalina.properties
-r--r----- 1 root    tomcat  1395 Feb  2 12:06 context.xml
-r--r----- 1 root    tomcat  1353 Jul 18 12:14 keystore
-r--r----- 1 root    tomcat  3257 Feb  2 12:06 logging.properties
-r--r----- 1 root    tomcat  6814 Jul 18 12:18 server.xml
-r--r----- 1 root    tomcat   210 Jul 18 12:10 tomcat-users.xml
-r--r----- 1 root    tomcat 51835 Feb  2 12:06 web.xml

Change the user/ownership of the $CATALINA_HOME/bin and $CATALINA_HOME/lib directories to be owned by the root user and have a group of tomcat:

# chown -R root:tomcat lib
# chown -R root:tomcat bin
# ls -l
total 92
drwxr-xr-x 2 root    tomcat  4096 Jul 15 16:05 bin
drwxr-xr-x 2 root    tomcat  4096 Jul 18 12:18 conf
drwxr-xr-x 2 root    tomcat  4096 Jul 15 16:03 lib
drwxr-xr-x 2 tomcat  tomcat  4096 Feb  2 12:04 logs
drwxr-xr-x 2 tomcat  tomcat  4096 Jul 15 16:03 temp
drwxr-xr-x 7 tomcat  tomcat  4096 Jul 15 16:04 webapps
drwxr-xr-x 2 tomcat  tomcat  4096 Feb  2 12:04 work

Resources

Tomcat as root and security issues
A lengthy thread in the tomcat-users mailing list archives dedicated to the perils of running Tomcat as the root user.

Removing Unused Web Applications

Rationale

It is generally good practice to remove any un-used web applications out of $CATALINA_HOME/webapps.
Tomcat "ships" with several default web applications you may want to consider removing if they are not being utilized:

The ROOT application is Tomcat's DocumentRoot and contains the server's main web page. Give thought to the content that is placed in ROOT/, as it will be readily available. (Note: if you want to utilize a robots.txt file to restrict crawler activity, ROOT/ is the place it will go.)
The manager application is used for remote management of web applications. To use this application, you must add a user with role of manager-gui in tomcat-users.xml. Obviously, if you are not planning to use the manager application, it should be removed.
The host-manager application is used for management of virtual hosts. To use this application, you must add a user with role of admin-gui in tomcat-users.xml. If you are not planning to do a lot of virtual hosting in Tomcat this application should be removed.
The examples application should probably be removed from a production server to minimize security exposure.
The docs are a copy of the Tomcat documentation found online. Unless you have need for a local copy, removing docs would help to tidy-up $CATALINA_HOME/webapps.

Using Digested Passwords

Rationale

Tomcat Realms

A realm element represents a "database" of usernames, passwords, and roles (similar to Unix groups) assigned to those users.

Passwords stored in clear text are a vulnerability if the host is compromised.
Better to have the passwords encrypted using a cryptographic hash functions (SHA, MD2, or MD5) and then stored in tomcat-users.xml file in the Tomcat conf/ directory.
Tomcat can be configured to support digested passwords (this is not the default setting).
How it works: When a client makes a request Tomcat will tell the client that a digested password is required. Based on this dialog, the client will automatically digest the password entered by the user.

Configure Tomcat to use digested passwords

First we need to enable digest passwords support in Tomcat by modifying a couple of Tomcat Realms in the server.xml file in the Tomcat conf/ directory.

A Tomcat Realm represents a "database" of usernames, passwords, and roles assigned to tomcat users.

Realm Name	Purpose
`UserDatabaseRealm`	The `UserDatabaseRealm` is enabled by default and reads clear text user password information stored in `tomcat-users.xml`.
`MemoryRealm`	The `MemoryRealm` reads the user password information stored in the `tomcat-users.xml` in a specified encrypted format.

Open the server.xml with your favorite editor:

$ vi server.xml

Locate the UserDatabaseRealm (right above the Host element) and comment it out:

<!-- This Realm uses the UserDatabase configured in the global JNDI
     resources under the key "UserDatabase".  Any edits
     that are performed against this UserDatabase are immediately
     available for use by the Realm.  -->
<!-- 
<Realm className="org.apache.catalina.realm.UserDatabaseRealm"
       resourceName="UserDatabase"/>
-->
<!-- Define the default virtual host
     Note: XML Schema validation will not work with Xerces 2.2.
-->
<Host name="localhost"  appBase="webapps"
      unpackWARs="true" autoDeploy="true"
      xmlValidation="false" xmlNamespaceAware="false">

Now add the following MemoryRealm information below the commented out UserDatabaseRealm:

<!-- This Realm uses the UserDatabase configured in the global JNDI
     resources under the key "UserDatabase".  Any edits
     that are performed against this UserDatabase are immediately
     available for use by the Realm.  -->
<!-- 
<Realm className="org.apache.catalina.realm.UserDatabaseRealm"
       resourceName="UserDatabase"/>
-->
<!-- Define the default virtual host
     Note: XML Schema validation will not work with Xerces 2.2.
-->

 <Realm className="org.apache.catalina.realm.MemoryRealm" 
                 digest="SHA" />

<Host name="localhost"  appBase="webapps"
      unpackWARs="true" autoDeploy="true"
      xmlValidation="false" xmlNamespaceAware="false">

Create a SHA encrypted version of your password.

Tomcat provides a script ($CATALINA_HOME/bin/digest.sh) that will encrypt a password string according to the algorithm specified. Use this script as follows with the password you made for yourself previously:

$ /home/tds/apache-tomcat-6.0.32/bin/digest.sh -a SHA secret
secret:e5e9fa1ba31ecd1ae84f75caaa474f3a663f05f4

Update tomcat-users.xml.

Replace your clear-text password in tomcat-users.xml with the encrypted version:

<tomcat-users>
    <role rolename="manager-gui"/>
    <user username="admin" password="e5e9fa1ba31ecd1ae84f75caaa474f3a663f05f4" roles="manager-gui"/>
</tomcat-users>

Verify digest passwords have been successfully enabled in Tomcat.

BASIC authentication

Since we are using BASIC authentication, you will need to clear any authenticated sessions in your browser to test whether digested passwords have been enabled.

Restart Tomcat and verify digest passwords have been successfully enabled by logging into the Tomcat manager application using your password in clear text: http://localhost:8080/manager/html/

Troubleshooting tips

Check the XML syntax in tomcat-users.xml and server.xml to make sure it is well-formed and without error.
Did you restart Tomcat after you made your changes to tomcat-users.xml and server.xml ?
Any errors will be reported in the catalina.out file in the Tomcat logs/ directory.
You do not need to type the encrypted version of your password into the browser (the browser auto-magically encrypts your password for you before it transmits it to the server).

Enabling SSL Encryption

How SSL works

For more information on how SSL works, Wikipedia details the steps involved during an SSL transaction.

Rationale

Communication between two servers can be intercepted (i.e., an http transaction between client and server).
An attacker can eavesdrop on the conversation and control the relay of messages between the victims, making them believe that they are talking directly to each other over a private connection.
The use of digital certificates adds a layer of security by allowing the receiver of the message to verify the sender is who he or she claims to be.
Any intercepted information that is encrypted also adds a layer of security (the attacker must take the extra step of unencrypting the data to view the message).
Secure Sockets Layer (SSL), and more recently Transport Layer Security (TLS), is a cryptographic protocol that provides security and data integrity for communications over TCP/IP networks.
SSL allows applications to communicate across a network in a way designed to prevent eavesdropping, tampering, and message forgery.
SSL uses a cryptographic system that uses two keys to encrypt data: a public key known to everyone and a private or secret key known only to the recipient of the message.
By convention, URLs that require an SSL connection start with https instead of http.

CA-signed Certificates

A self-signed certificate says to your users "Trust me - I am who I say I am."

A certificate signed by a CA says, "Trust me - the CA agrees I am who I say I am."

SSL certificates

A public key certificate is an electronic document which incorporates a digital signature to bind together a public key with identity information of the certificate user.
The certificate can be used to verify that a public key belongs to an individual.
The digital signature can be signed by a Certificate Authority (CA) or the certificate user (a self-signed certificate).
Unidata highly recommends the use of a certificate signed by a Certificate Authority (CA).
Browser warnings for self-signed certificates can be very confusing to users.
It's about trust: CA-signed certificates verify your identify to your users. If the traffic between your server and the client is intercepted, an attacker can inject their own self-signed cert in the place of yours and the visitor will likely not notice.
Self-signed certificates cannot (by nature) be revoked, which may allow an attacker who has already gained access to monitor and inject data into a connection to spoof an identity if a private key has been compromised. CAs on the other hand have the ability to revoke a compromised certificate, which prevents its further use.

Certificate `keystore` file

A keystore file stores the details of the SSL certificate necessary to make the protocol secured.
The Tomcat documentation includes a section on importing your certificate into a keystore file.
Tomcat uses the keystore file for SSL transactions.

Accessing the TDS remote management tool

Other than the compelling security reasons, you will want to enable SSL to take advantage of the TDS remote management tool which (out-of-the-box) requires SSL in order to access: http://localhost:8080/thredds/admin/debug

Configure Tomcat to enable SSL and use the self-signed certificate.

Based on what we know about Tomcat configuration, which file in $CATALINA_HOME/conf should we edit to to enable SSL?

Open $CATALINA_HOME/conf/server.xml with your favorite editor:

$ vi server.xml

Locate the Java HTTP/1.1 Connector listening on port 8080 and verify it is redirecting SSL traffic to port 8443:

<Connector port="8080" protocol="HTTP/1.1"
              connectionTimeout="20000"
              redirectPort="8443" />

Find and uncomment the SSL HTTP/1.1 Connector listening on port 8443 to activate this connector:

<Connector port="8443" protocol="HTTP/1.1" SSLEnabled="true"
              maxThreads="150" scheme="https" secure="true"
              clientAuth="false" sslProtocol="TLS" />

Add a keystoreFile attribute to the SSL HTTP/1.1 Connector to tell Tomcat where to find your keystore:

<Connector port="8443" protocol="HTTP/1.1" SSLEnabled="true"
              maxThreads="150" scheme="https" secure="true"
              clientAuth="false" sslProtocol="TLS" keystoreFile="/home/tds/tds/apache-tomcat-6.0.32/conf/keystore" />

Since we opted to not use the default keystore password, we need to specify the new password so Tomcat can open the file:

<Connector port="8443" protocol="HTTP/1.1" SSLEnabled="true"
              maxThreads="150" scheme="https" secure="true"
              clientAuth="false" sslProtocol="TLS" keystoreFile="/home/tds/tds/apache-tomcat-6.0.32/conf/keystore" keystorePass="foobar" />

Finally, verify the AprLifecycleListener is uncommented (found near the top of the file):

<!--APR library loader. Documentation at /docs/apr.html -->
<Listener className="org.apache.catalina.core.AprLifecycleListener" SSLEngine="on" />

Verify SSL has been enabled.

Restart Tomcat:

$ $CATALINA_HOME/bin/shutdown.sh
$ $CATALINA_HOME/bin/startup.sh

Verify Tomcat is listening on port 8443 by running the netstat command:

$ netstat -an | grep tcp | grep 8443

`man netstat`

Run man netstat in your terminal window to learn more about this command.

netstat (short for network statistics) is available on Unix, Unix-like, and Windows NT-based operating systems. It is a command-line tool that displays:

network connections (both incoming and outgoing)
routing tables
and a number of network interface statistics

Look for the following in the output:

tcp        0      0 0.0.0.0:8443               0.0.0.0:*                   LISTEN

Troubleshooting tips

Check the XML syntax in server.xml to make sure it is well-formed and without error.
When generating the self-signed certificate, the last password (the key password) and keystore password should be the same (changeit). If they differ, Tomcat cannot open the keystore and you will get this error: java.io.IOException: Cannot recover key.
Did you restart Tomcat after you made your changes to server.xml?
Did you specify the full path to the keystore file in server.xml?

Modify $CATALINA_HOME/conf/tomcat-users.xml to add a new role with the rolename attribute of tdsConfig, and add this role to your list of roles:

<tomcat-users>
    <role rolename="manager-gui"/>
    <role rolename="tdsConfig"/>
    <user username="admin" password="e5e9fa1ba31ecd1ae84f75caaa474f3a663f05f4" roles="manager-gui,tdsConfig"/>
</tomcat-users>

Restart Tomcat and try to access the TDS remote management tool: http://localhost:8080/thredds/admin/debug/

Configuring web applications for SSL

How did Tomcat know to use SSL for the TDS remote management tool?

Where, in any of the configuration changes you made to $CATALINA_HOME/conf/server.xml or $CATALINA_HOME/conf/tomcat-users.xml, did you explicitly specify that TDS remote management tool must be accessed via SSL?

The missing piece: `/WEB-INF/web.xml`

This is specified in the web application deployment descriptor, aka web.xml.
Deployment descriptors are found in the WEB-INF directory of the web application: <application name>/WEB-INF/web.xml.
By convention, Tomcat and other servlet containers will read the web application deployment descriptors for initialization parameters and container-managed security constraints upon application deployment.
The TDS has been pre-configured to require that SSL encryption is enabled in order to access the remote management tool.

Looking at the TDS deployment descriptor

Have a look at the deployment descriptor that comes with the TDS.

Navigate to the unpacked thredds directory in $CATALINA_HOME/webapps, and view the file:

$ cd /home/tds/tds/apache-tomcat-6.0.32/webapps/thredds
$ less WEB-INF/web.xml

Look for a reference to the TDS remote management tool's URL (/admin/debug).

Near the bottom of the deployment descriptor you will find this entry:

  <!-- This allows "remote configuration":
    /thredds/admin/debug gives access to various debug and status info.
    /thredds/admin/content/ -> "{tomcat_home}/content/thredds/"
    /thredds/admin/root/ -> "{tomcat_home}/webapps/thredds/" DISABLED
    /thredds/admin/dataDir/path -> "{dataRoot(path)}/webapps/thredds/"  DISABLED
   -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>sensitive read access</web-resource-name>
      <url-pattern>/admin/*</url-pattern>
      <http-method>GET</http-method>
      <!-- http-method>PUT</http-method -->
    </web-resource-collection>
    <auth-constraint>
      <role-name>tdsConfig</role-name>
    </auth-constraint>
    <user-data-constraint>
      <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>

Configuration help

For more information on how to configure security requirements for a web application in a deployment descriptor, see: Defining Security Requirements for Web Applications.

The <user-data-constraint> establishes a requirement that the constrained requests be received over a protected transport layer connection. This guarantees how the data will be transported between client and server.
<transport-guarantee> choices for type of transport guarantee include NONE, INTEGRAL, and CONFIDENTIAL:

Specify CONFIDENTIAL when the application requires that data be transmitted so as to prevent other entities from observing the contents of the transmission. (E.g., via SSL.)
Specify INTEGRAL when the application requires that the data be sent between client and server in such a way that it cannot be changed in transit.
Specify NONE to indicate that the container must accept the constrained requests on any connection, including an unprotected one.

Changes to the `manager` application

The manager application URLs and roles has been re-structured. See the Tomcat Migration guide for more information.

Enabling SSL for the Tomcat `manager` application

Modify the deployment descriptor of the Tomcat manager application.

If you are using Tomcat version 6.0.29 or older:

Using your favorite editor, open the deployment descriptor for the Tomcat manager application:

$ vi $CATALINA_HOME/webapps/manager/WEB-INF/web.xml

Locate the <security-constraint> element (near the bottom of the file):

  <!-- Define a Security Constraint on this Application -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>HTMLManger and Manager command</web-resource-name>
      <url-pattern>/jmxproxy/*</url-pattern>
      <url-pattern>/html/*</url-pattern>
      <url-pattern>/list</url-pattern>
      <url-pattern>/expire</url-pattern>
      <url-pattern>/sessions</url-pattern>
      <url-pattern>/start</url-pattern>
      <url-pattern>/stop</url-pattern>
      <url-pattern>/install</url-pattern>
      <url-pattern>/remove</url-pattern>
      <url-pattern>/deploy</url-pattern>
      <url-pattern>/undeploy</url-pattern>
      <url-pattern>/reload</url-pattern>
      <url-pattern>/save</url-pattern>
      <url-pattern>/serverinfo</url-pattern>
      <url-pattern>/status/*</url-pattern>
      <url-pattern>/roles</url-pattern>
      <url-pattern>/resources</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE:  This role is not present in the default users file -->
       <role-name>manager</role-name>
    </auth-constraint>
  </security-constraint>

Add a <user-data-constraint> with a <transport-guarantee> of CONFIDENTIAL to enable port-forwarding to port 8443:

  <!-- Define a Security Constraint on this Application -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>HTMLManger and Manager command</web-resource-name>
      <url-pattern>/jmxproxy/*</url-pattern>
      <url-pattern>/html/*</url-pattern>
      <url-pattern>/list</url-pattern>
      <url-pattern>/expire</url-pattern>
      <url-pattern>/sessions</url-pattern>
      <url-pattern>/start</url-pattern>
      <url-pattern>/stop</url-pattern>
      <url-pattern>/install</url-pattern>
      <url-pattern>/remove</url-pattern>
      <url-pattern>/deploy</url-pattern>
      <url-pattern>/undeploy</url-pattern>
      <url-pattern>/reload</url-pattern>
      <url-pattern>/save</url-pattern>
      <url-pattern>/serverinfo</url-pattern>
      <url-pattern>/status/*</url-pattern>
      <url-pattern>/roles</url-pattern>
      <url-pattern>/resources</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager</role-name>
    </auth-constraint>
    <user-data-constraint>
       <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>

If you are using Tomcat version 6.0.30 or 6.0.32:

Using your favorite editor, open the deployment descriptor for the Tomcat manager application:

$ vi $CATALINA_HOME/webapps/manager/WEB-INF/web.xml

Locate the <security-constraint> element (near the bottom of the file):

  <!-- Define a Security Constraint on this Application -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Manager commands</web-resource-name>
      <url-pattern>/list</url-pattern>
      <url-pattern>/expire</url-pattern>
      <url-pattern>/sessions</url-pattern>
      <url-pattern>/start</url-pattern>
      <url-pattern>/stop</url-pattern>
      <url-pattern>/install</url-pattern>
      <url-pattern>/remove</url-pattern>
      <url-pattern>/deploy</url-pattern>
      <url-pattern>/undeploy</url-pattern>
      <url-pattern>/reload</url-pattern>
      <url-pattern>/save</url-pattern>
      <url-pattern>/serverinfo</url-pattern>
      <url-pattern>/roles</url-pattern>
      <url-pattern>/resources</url-pattern>
      <url-pattern>/findleaks</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7.
                  3. Use the manager-script role to take advantage of the new
                     CSRF protection. Using the manager role or assigning both
                     the manager-script and manager-gui roles to the same user
                     will bypass the CSRF protection. -->
       <role-name>manager-script</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>HTML Manager commands</web-resource-name>
      <url-pattern>/html/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7.
                  3. Use just the manager-gui role to take advantage of the new
                     CSRF protection. Assigning the manager role or manager-gui
                     role along with either the manager-script or manager-jmx
                     roles to the same user will bypass the CSRF protection. -->
       <role-name>manager-gui</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
  </security-constraint>

  <security-constraint>
    <web-resource-collection>
      <web-resource-name>JMX proxy</web-resource-name>
      <url-pattern>/jmxproxy/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7.
                  3. Use the manager-jmx role to take advantage of the new
                     CSRF protection. Using the manager role or assigning both
                     the manager-jmx and manager-gui roles to the same user
                     will bypass the CSRF protection. -->
       <role-name>manager-jmx</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Status</web-resource-name>
      <url-pattern>/status/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7. -->
       <role-name>manager-status</role-name>
       <role-name>manager-gui</role-name>
       <role-name>manager-script</role-name>
       <role-name>manager-jmx</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
  </security-constraint>

The manager application deployment descriptor for these later versions of Tomcat 6 has been modified to be similar to the configuration the manager application as it appears in Tomcat 7. The deployment descriptor contains a <security-constraint> section for three of the ContactPaths (as per Manager Application section of the Tomcat Migration Guide), as well as a 'catch all' <security-constraint> to handle the various script-oriented manager commands found in earlier versions of Tomcat 6.

Add a <user-data-constraint> with a <transport-guarantee> of CONFIDENTIAL for the desired ContactPaths to to enable port-forwarding to port 8443:

  <!-- Define a Security Constraint on this Application -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Manager commands</web-resource-name>
      <url-pattern>/list</url-pattern>
      <url-pattern>/expire</url-pattern>
      <url-pattern>/sessions</url-pattern>
      <url-pattern>/start</url-pattern>
      <url-pattern>/stop</url-pattern>
      <url-pattern>/install</url-pattern>
      <url-pattern>/remove</url-pattern>
      <url-pattern>/deploy</url-pattern>
      <url-pattern>/undeploy</url-pattern>
      <url-pattern>/reload</url-pattern>
      <url-pattern>/save</url-pattern>
      <url-pattern>/serverinfo</url-pattern>
      <url-pattern>/roles</url-pattern>
      <url-pattern>/resources</url-pattern>
      <url-pattern>/findleaks</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7.
                  3. Use the manager-script role to take advantage of the new
                     CSRF protection. Using the manager role or assigning both
                     the manager-script and manager-gui roles to the same user
                     will bypass the CSRF protection. -->
       <role-name>manager-script</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>HTML Manager commands</web-resource-name>
      <url-pattern>/html/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7.
                  3. Use just the manager-gui role to take advantage of the new
                     CSRF protection. Assigning the manager role or manager-gui
                     role along with either the manager-script or manager-jmx
                     roles to the same user will bypass the CSRF protection. -->
       <role-name>manager-gui</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>

  <security-constraint>
    <web-resource-collection>
      <web-resource-name>JMX proxy</web-resource-name>
      <url-pattern>/jmxproxy/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7.
                  3. Use the manager-jmx role to take advantage of the new
                     CSRF protection. Using the manager role or assigning both
                     the manager-jmx and manager-gui roles to the same user
                     will bypass the CSRF protection. -->
       <role-name>manager-jmx</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Status</web-resource-name>
      <url-pattern>/status/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <!-- NOTE: 1. These roles are not present in the default users file
                  2. The manager role is deprecated, it will be removed in
                     Tomcat 7. -->
       <role-name>manager-status</role-name>
       <role-name>manager-gui</role-name>
       <role-name>manager-script</role-name>
       <role-name>manager-jmx</role-name>
       <role-name>manager</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>

If you are using Tomcat 7:

Using your favorite editor, open the deployment descriptor for the Tomcat manager application:

$ vi $CATALINA_HOME/webapps/manager/WEB-INF/web.xml

Locate the <security-constraint> elements (near the bottom of the file):

  <!-- Define a Security Constraint on this Application -->
  <!-- NOTE:  None of these roles are present in the default users file -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>HTML Manager interface (for humans)</web-resource-name>
      <url-pattern>/html/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-gui</role-name>
    </auth-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Text Manager interface (for scripts)</web-resource-name>
      <url-pattern>/text/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-script</role-name>
    </auth-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>JMX Proxy interface</web-resource-name>
      <url-pattern>/jmxproxy/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-jmx</role-name>
    </auth-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Status interface</web-resource-name>
      <url-pattern>/status/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-gui</role-name>
       <role-name>manager-script</role-name>
       <role-name>manager-jmx</role-name>
       <role-name>manager-status</role-name>
    </auth-constraint>
  </security-constraint>

The Tomcat 7 version of the manager application deployment descriptor contains a <security-constraint> section for each of the four possible ContactPaths (as per Manager Application section of the Tomcat Migration Guide).

Add a <user-data-constraint> with a <transport-guarantee> of CONFIDENTIAL for the desired ContactPaths to to enable port-forwarding to port 8443:

  <!-- Define a Security Constraint on this Application -->
  <!-- NOTE:  None of these roles are present in the default users file -->
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>HTML Manager interface (for humans)</web-resource-name>
      <url-pattern>/html/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-gui</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Text Manager interface (for scripts)</web-resource-name>
      <url-pattern>/text/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-script</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>JMX Proxy interface</web-resource-name>
      <url-pattern>/jmxproxy/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-jmx</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>
  <security-constraint>
    <web-resource-collection>
      <web-resource-name>Status interface</web-resource-name>
      <url-pattern>/status/*</url-pattern>
    </web-resource-collection>
    <auth-constraint>
       <role-name>manager-gui</role-name>
       <role-name>manager-script</role-name>
       <role-name>manager-jmx</role-name>
       <role-name>manager-status</role-name>
    </auth-constraint>
    <user-data-constraint>
        <transport-guarantee>CONFIDENTIAL</transport-guarantee>
    </user-data-constraint>
  </security-constraint>

Verify SSL has been enabled for the Tomcat manager application.

Restart Tomcat and verify SSL has been enabled for the Tomcat manager application: http://localhost:8080/manager/html/

Troubleshooting tips

Check the XML syntax in web.xml to make sure it is well-formed and without error.
Did you specify a <transport-guarantee> of CONFIDENTIAL?
Did you restart Tomcat after you made your changes to web.xml?

Resources

SSL Configuration HOW-TO
The Apache Tomcat document detailing how to enable SSL.
Tomcat Migration Guide
A document detailing the various changes between Tomcat versions.
When are self-signed certificates acceptable?
A compelling argument as to why self-signed certificates should not be used in a production environment.

TDS Tutorial: Tomcat and TDS Security

Best practices and recommendations on securing a production TDS/Tomcat server.

Be afraid

Rationale

Resources

Rationale

Background info

Creating a dedicated Tomcat user/group & setting permissions in $CATALINA_HOME

Resources

Rationale

Rationale

Tomcat Realms

Configure Tomcat to use digested passwords

BASIC authentication

Troubleshooting tips

How SSL works

Rationale

CA-signed Certificates

SSL certificates

Certificate keystore file

Accessing the TDS remote management tool

man netstat

Troubleshooting tips

Configuring web applications for SSL

The missing piece: /WEB-INF/web.xml

Looking at the TDS deployment descriptor

Configuration help

Changes to the manager application

Enabling SSL for the Tomcat manager application

Troubleshooting tips

Resources

Rationale

Port Tinkering

For running the TDS, keep in mind the following:

Resources

Tomcat Valves

Rationale

Examples

Resources

Changes to the manager application

Rationale

Resources

Rationale

Resources

Rationale

Resources

SHUTDOWN on port 8005

Tomcat Version Information

Creating a dedicated Tomcat user/group & setting permissions in `$CATALINA_HOME`

Certificate `keystore` file

`man netstat`

The missing piece: `/WEB-INF/web.xml`

Changes to the `manager` application

Enabling SSL for the Tomcat `manager` application

Changes to the `manager` application

`SHUTDOWN` on port 8005