I am posting this question here because JBoss is using Tomcat internally. 1. server.xml has the context path defined: <Host name="localhost" autoDeploy="false" deployOnStartup="false" deployXML="false"> <Context path="/myContextPath"/> </Host> and is also configured for ssl: <Connector port="8443" address="${jboss.bind.address}" maxThreads="100" strategy="ms" maxHttpHeaderSize="8192" emptySessionPath="true" scheme="https" secure="true" clientAuth="false" sslProtocol = "TLS" keystoreFile="${jboss.server.home.dir}/conf/server.keystore" keystorePass="123456" truststoreFile="${jboss.server.home.dir}/conf/server.truststore" truststorePass="123456" /> 2. web.xml has <servlet> <servlet-name>MyServlet</servlet-name> <servlet-class>com.xyz.MyServlet</servlet-class> </servlet> <servlet-mapping> <servlet-name>MyServlet</servlet-name> <url-pattern>/somePath/*</url-pattern> </servlet-mapping> This is under web-inf inside the myContextPath war file 3. JBoss console window shows: Error starting static Resources java.lang.IllegalArgumentException: Document base C:\Program Files\jboss-4.0.4.GA\server\default\.\myContextPath does not exist or is not a readable directory The client gets the following error message: Server returned HTTP response code: 500 for URL: https://localhost:8443/myContextPath/somePath/MyServlet My question is why is the path whacked out like C:\Program Files\jboss-4.0.4.GA\server\default\.\myContextPath instead of pointing to the right directory which is : C:\Program Files\jboss-4.0.4.GA\server\default\deploy (the war file is in this directory) How can I make JBoss/Tomcat point to the right directory? TIA