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Issue replacing certificates in Tomcat 6

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Hello.  I've struggled finding a solution for this issue.  I have a number of Tomcat 6 servers.  Many of them need new certificates.  I've made new cert/key pairs, and set them up in the server.xml file.  I restart the tomcat service, then try to connect.  The browser just spins, and never connects.  No cert error, no nothing. Tomcat is running.  It's just not responding.  If I put back the original cert/key, it works fine again.  Any help would be appreciated.  
Tim Barnby
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I forgot to mention a few details.  

I generate the key/cert with the following command:
openssl req -x509 -nodes -sha256 -days 365 -newkey rsa:2048 -keyout NewTomcat.key -out NewTomcat.crt

The Connector looks like this:
              enableLookups="false" disableUploadTimeout="true"
              acceptCount="100" scheme="https" secure="true"
              SSLCertificateKeyFile="${catalina.base}/conf/OldTomcat.key" />
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