Hi, I just want to share my experience installing Tomcat 5.5.23 (and also 5.5.27 from memory) on Windows Server 2003 Datacenter Edition. I installed 5.5.27 on that version of Windows by creating an instance on Amazon EC2. Tomcat worked pretty quickly on port 80. I needed to enable HTTPS so I copied the SSL certificate that was used on my development machine, made the proper changes in the Tomcat config, restarted the server but accessing https://localhost would hang for a while and then timeout. I questioned everything: my Tomcat config, my EC2 instance config, my app, my certificate for almost a week. Searching the Tomcat for "windows HTTPS" mail archive today gave me a hint to solve the issue. I found and deleted the "tc-native.dll" file, restarted Tomcat and the HTTPS connection worked straight away.
I am not a Tomcat expert but I installed it many times (probably over 20 times) on machines running Windows XP Pro and Windows Enterprise and Small Business Server and I didn't encounter that issue. It might have been a diffferent version of Tomcat 5.5.x, so I don't know how I didn't hit that problem before. I want to mention as well that the logs didn't show any error at all and that Tomcat, mySQL and my app worked great on 3 other machines with XP Pro and SBS. Just sharing for the next person banging her/his head... Fred