I installed tomcat 5.5.20 + e-mail patch on windows 2003 server manually and ran into an SSL issue. Port 443 was listening and accepting requests but not using the certificate. Therefore https://ourcpasserver did not work, but http://ourcpasserver:443 did work, but in non-secure mode (i.e. it wasn't properly using the cert)

Selecting the SSL option in CPAS was timing out or giving an HTTP handshake failure message after clicking save.

I found the problem with SSL that I was having was due to the native .dll tomcat file (tcnative-1.dll). We are using a PKCS12 certificate (microsoft .pfx file converted to .p12 file via openssl) which apparently has conflicts with the tcnative-1.dll file. All I did was to rename %ProgramFiles%\Apache Software Foundation\Tomcat 5.5\bin\tcnative-1.dll to tcnative-1.dll~ and SSL began working like a champ. I was then able to select the SSL option within CPAS admin console, also.