I might be wrong, but this is the way it was explained to me -- It can't be done since the cert is tied to an ip / port, not a server name. And the cert is given back to the browser before the server has any idea what URL the browser is going to. What I think you could do (but I haven't tried myself) is to set up the server with multiple IP addresses, and configure multiple Tomcat connectors, one per IP address, each with its own keystore. Or basically do the same thing, but with one IP address, and each connector running on a different port.
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