implement a logger so you can trace whats going on
http://tomcat.apache.org/tomcat-5.5-doc/logging.html

also in %TOMCAT_HOME/conf/server.xml crankup the debug attribute on your 
<Connector statement
debug="5"
http://tomcat.apache.org/tomcat-4.0-doc/config/http11.html
and you'll see lots of messages in tomcat console

HTH
Martin 
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> Subject: SSL https clientAuth debugging assistance
> Date: Mon, 8 Sep 2008 11:49:04 -0500
> From: [EMAIL PROTECTED]
> To: users@tomcat.apache.org
> 
> We have just started using Tomcat.  We are using version 5.5.26.
> 
> I was able to set up Tomcat and get it running with our application.  I
> also have enabled SSL:
>    <Connector port="18443" maxHttpHeaderSize="8192"
>                maxThreads="150" minSpareThreads="25"
> maxSpareThreads="75"
>                enableLookups="false" disableUploadTimeout="true"
>                acceptCount="100" scheme="https" secure="true"
>                clientAuth="false" sslProtocol="TLS"
>                keystoreFile="conf/keystore" keyAlias="tomcat" />
> 
> I have one user that needs use to authenticate their client.  I have
> this working on our development system (added their certificate to our
> keystore) but following the same process to our test box is failing.
> The client (which I don't have access to) is giving a very generic error
> message.
> 
> Is there a way that I can see why the client is failing the connection
> (i.e. certificate doesn't match client, certificate expired, ...) or get
> more debugging information from the Tomcat side?
> 
> Thanks
> Tim

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