Setting up tomcat + ssl failed.. cannot connect to SSL channel? - configuration

Question

I'm trying to get Tomcat 6.0.20 working with SSL authentication. I used keytool to create a new certificate, put it into my user dir, and set the tomcat authentication to this (server.xml):
(Omitted)
-->
<Server port="8005" shutdown="SHUTDOWN">
<!--APR library loader. Documentation at /docs/apr.html -->
<Listener className="org.apache.catalina.core.AprLifecycleListener" SSLEngine="on" SSLRandomSeed="builtin" />
<!--Initialize Jasper prior to webapps are loaded. Documentation at /docs/jasper-howto.html -->
<Listener className="org.apache.catalina.core.JasperListener" />
<!-- JMX Support for the Tomcat server. Documentation at /docs/non-existent.html -->
<Listener className="org.apache.catalina.mbeans.ServerLifecycleListener" />
<Listener className="org.apache.catalina.mbeans.GlobalResourcesLifecycleListener" />
<!-- Global JNDI resources
Documentation at /docs/jndi-resources-howto.html
-->
<GlobalNamingResources>
<!-- Editable user database that can also be used by
UserDatabaseRealm to authenticate users
-->
<Resource name="UserDatabase" auth="Container"
type="org.apache.catalina.UserDatabase"
description="User database that can be updated and saved"
factory="org.apache.catalina.users.MemoryUserDatabaseFactory"
pathname="conf/tomcat-users.xml" />
</GlobalNamingResources>
<!-- A "Service" is a collection of one or more "Connectors" that share
a single "Container" Note: A "Service" is not itself a "Container",
so you may not define subcomponents such as "Valves" at this level.
Documentation at /docs/config/service.html
-->
<Service name="Catalina">
<!--The connectors can use a shared executor, you can define one or more named thread pools-->
<!--
<Executor name="tomcatThreadPool" namePrefix="catalina-exec-"
maxThreads="150" minSpareThreads="4"/>
-->
<!-- A "Connector" represents an endpoint by which requests are received
and responses are returned. Documentation at :
Java HTTP Connector: /docs/config/http.html (blocking & non-blocking)
Java AJP Connector: /docs/config/ajp.html
APR (HTTP/AJP) Connector: /docs/apr.html
Define a non-SSL HTTP/1.1 Connector on port 8080
-->
<Connector port="9090" protocol="HTTP/1.1"
connectionTimeout="20000"
redirectPort="9091" />
<!-- A "Connector" using the shared thread pool-->
<!--
<Connector executor="tomcatThreadPool"
port="8080" protocol="HTTP/1.1"
connectionTimeout="20000"
redirectPort="8443" />
-->
<!-- Define a SSL HTTP/1.1 Connector on port 8443
This connector uses the JSSE configuration, when using APR, the
connector should be using the OpenSSL style configuration
described in the APR documentation -->
<Connector port="9091" protocol="HTTP/1.1" SSLEnabled="true"
maxThreads="150" scheme="https" secure="true"
keystoreFile="/home/media/.keystore"
keystorePass="123456"
clientAuth="false" sslProtocol="TLS" />
<!-- Define an AJP 1.3 Connector on port 8009 -->
<Connector port="8009" protocol="AJP/1.3" redirectPort="9091" />
<!-- An Engine represents the entry point (within Catalina) that processes
every request. The Engine implementation for Tomcat stand alone
analyzes the HTTP headers included with the request, and passes them
on to the appropriate Host (virtual host).
Documentation at /docs/config/engine.html -->
<!-- You should set jvmRoute to support load-balancing via AJP ie :
<Engine name="Catalina" defaultHost="localhost" jvmRoute="jvm1">
-->
<Engine name="Catalina" defaultHost="localhost">
<!--For clustering, please take a look at documentation at:
/docs/cluster-howto.html (simple how to)
/docs/config/cluster.html (reference documentation) -->
<!--
<Cluster className="org.apache.catalina.ha.tcp.SimpleTcpCluster"/>
-->
<!-- The request dumper valve dumps useful debugging information about
the request and response data received and sent by Tomcat.
Documentation at: /docs/config/valve.html -->
<!--
<Valve className="org.apache.catalina.valves.RequestDumperValve"/>
-->
<!-- 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">
<!-- SingleSignOn valve, share authentication between web applications
Documentation at: /docs/config/valve.html -->
<!--
<Valve className="org.apache.catalina.authenticator.SingleSignOn" />
-->
<!-- Access log processes all example.
Documentation at: /docs/config/valve.html -->
<!--
<Valve className="org.apache.catalina.valves.AccessLogValve" directory="logs"
prefix="localhost_access_log." suffix=".txt" pattern="common" resolveHosts="false"/>
-->
</Host>
</Engine>
</Service>
</Server>
However, whist connection thru http is fine, whenever I try to connect through port 9091 (https) I always get the message "the connection was interrupted". I never got a certificate or anything, though there was no errors in catalina.out
What could be wrong. Must I generate a OpenSSL key pair and import it in addition to creating and specifying a keystore?

Answer 1

I'd suggest using curl to troubleshoot your problems. curl is a unix tool as well as a library, and on Windows is runs well under cygwin. Try the following command:
curl -Iv https://yourhost:9091
You should see some output which looks something like this:
* About to connect() to yourhost port 9091 (#0)
* Trying 67.207.137.114... connected
* Connected to yourhost (67.207.137.114) port 9091 (#0)
* successfully set certificate verify locations:
* CAfile: none
CApath: /etc/ssl/certs
* SSLv3, TLS handshake, Client hello (1):
* SSLv3, TLS handshake, Server hello (2):
* SSLv3, TLS handshake, CERT (11):
* SSLv3, TLS alert, Server hello (2):
* SSL certificate problem, verify that the CA cert is OK. Details:
From here you should be able to narrow down where to troubleshoot.