We have a Java web services application which interrogates a SQL server 2005 database. If I have imported a client SSL certificate from the SQL Server to the java keystore and updated the JNDI connection in Tomcats context.xml file and the connector in the server.xml file, how can I check that the communication is indeed being encypted?
I don't think that's how it's supposed to work. The Tomcat keystore is primarily for holding keys that clients use to communicate with Tomcat, not that Tomcat apps or components use as clients to other servers.
Regardless, you'd have to configure any secure communications between the database connection pooler and the database as part of configuring the connection pooler. That would be done by setting the appropriate JDBC Connection properties for the pool. This should help: