Sharing servlet context across web applications in same server?

It looks fine so far. Apparently it's been overridden by a context. Xml maintained/generated elsewhere.

You can read in the Tomcat's Context configuration reference about the rules. Do you for example have one in webapp's META-INF? You should then define crossContext in there.

According to J2EE every context has its own session management. You cannot share a session across two different servlet context. You will need to pass the jessionid back and forth between context.

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