Index: src/main/java/org/wso2/carbon/tomcat/ext/internal/CarbonTomcatServiceComponent.java
===================================================================
--- src/main/java/org/wso2/carbon/tomcat/ext/internal/CarbonTomcatServiceComponent.java	(revision 136188)
+++ src/main/java/org/wso2/carbon/tomcat/ext/internal/CarbonTomcatServiceComponent.java	(working copy)
@@ -2,7 +2,6 @@
 
 
 import org.apache.catalina.Context;
-import org.apache.catalina.Wrapper;
 import org.apache.catalina.startup.Tomcat;
 import org.apache.commons.logging.Log;
 import org.apache.commons.logging.LogFactory;
@@ -10,7 +9,6 @@
 import org.wso2.carbon.base.api.ServerConfigurationService;
 import org.wso2.carbon.tomcat.CarbonTomcatException;
 import org.wso2.carbon.tomcat.api.CarbonTomcatService;
-import org.wso2.carbon.tomcat.ext.servlet.DelegationServlet;
 import org.wso2.carbon.tomcat.ext.transport.ServletTransportManager;
 
 import java.io.File;
@@ -56,6 +54,17 @@
         } catch (CarbonTomcatException exception) {
             log.error("Error while adding the carbon web-app", exception);
         }
+
+        // Add a dummy context "/t" to dispatch requests to tenant webapps when the tenant is not
+        // loaded yet. This is needed in a situation where the webContextRoot is set.
+        File tenantDummyCtxDir = Utils.createDummyTenantContextDir();
+        if (tenantDummyCtxDir.exists()) {
+            try {
+                carbonTomcatService.addWebApp("/t", tenantDummyCtxDir.getPath());
+            } catch (CarbonTomcatException exception) {
+                log.error("Error while adding the dummy tenant context web-app", exception);
+            }
+        }
     }
 
     @SuppressWarnings("unused")
Index: src/main/java/org/wso2/carbon/tomcat/ext/internal/Utils.java
===================================================================
--- src/main/java/org/wso2/carbon/tomcat/ext/internal/Utils.java	(revision 136188)
+++ src/main/java/org/wso2/carbon/tomcat/ext/internal/Utils.java	(working copy)
@@ -19,10 +19,12 @@
 
 import org.apache.catalina.connector.Request;
 import org.wso2.carbon.context.ApplicationContext;
+import org.wso2.carbon.utils.CarbonUtils;
 import org.wso2.carbon.utils.multitenancy.MultitenantConstants;
 
 import javax.servlet.http.HttpServletRequest;
 import javax.servlet.http.HttpSession;
+import java.io.File;
 
 /**
  * A collection of useful utility methods
@@ -114,4 +116,13 @@
         }
         return appName;
     }
+
+    public static File createDummyTenantContextDir() {
+        File dummyCtxFile = new File(CarbonUtils.getTmpDir() + File.separator + "t");
+        if (!dummyCtxFile.exists() && !dummyCtxFile.mkdir()) {
+            return null;
+        } else {
+            return dummyCtxFile;
+        }
+    }
 }