To be able to use multiple certificates on the same IP address and port, you need server name support. Unfortunately, this was introduced in Java 7, only on the client side .
(There are still problems with SNI support on the client side. SNI, especially due to the lack of support from any version of IE on Win XP, Java 6 and below, and some mobile browsers.)
The workaround for this is to use a single certificate that supports multiple host names. The preferred way to do this is to have a certificate with multiple objects with an alternate object name (SAN). Otherwise, if the names have a pattern, a wildcard certificate may be appropriate (e.g. *.example.com for www.example.com and secure.example.com ).
Apache Httpd supports SNI , so you can solve your problem by using different VirtualHost for each hostname you want to serve, and use a reverse proxy to a different Tomcat configuration for each host.
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