I set up an EAR with several modules. The EAR is deployed to "/lams" context path. The main module uses ServletExtension to catch authentication URLs and do some magic. deploymentInfo.addOuterHandlerChainWrapper( new HandlerWrapper() { public HttpHandler wrap( final HttpHandler handler) { return Handlers.path(handler).addExactPath( "/j_security_check" , new HttpHandler() { //magic }); }}); So a PathHandler is in use. When I access an exact resource, like this http://localhost:8080/lams/index.jsp everything works fine. When I access just the context path http://localhost:8080/lams PathHandler throws Exception handling request to /lams/: java.lang.StringIndexOutOfBoundsException: String index out of range: -4 The reason for that is PathHandler.handleRequest() method. It expects exchange.requestPath to be the full path. But in the method values are: exchange.requestPath = /lams/ exchange.relativePath = /index.jsp When substring is attempted in line #89, it does not take into account that requestPath is not the full path, just the "browser path", and causes the exception. It seems either PathHandler (not expecting this situation) or HttpServerExchange (not filling the fields right) issue. I can not post the source code as it is pretty big.