diff --git a/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/Tomcat8xStandaloneLocalConfiguration.java b/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/Tomcat8xStandaloneLocalConfiguration.java
index e4879dd70f..7afd8fe39d 100644
--- a/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/Tomcat8xStandaloneLocalConfiguration.java
+++ b/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/Tomcat8xStandaloneLocalConfiguration.java
@@ -203,10 +203,16 @@ private void writeDirectoryPostResource(Element postResourceEl, String path)
      */
     private void writeJarPostResource(StringBuilder sb, String path)
     {
+      if (Boolean.parseBoolean(getPropertyValue(TomcatPropertySet.CONTEXT_MAPJARSTOWEBINFCLASSES))) {
+        sb.append("className=\"" + JAR_RESOURCE_SET + "\" base=\"");
+        sb.append(path.replace("&", "&"));
+        sb.append("\" webAppMount=\"/WEB-INF/classes/");
+      } else {
         sb.append("className=\"" + FILE_RESOURCE_SET + "\" base=\"");
         sb.append(path.replace("&", "&"));
         sb.append("\" webAppMount=\"/WEB-INF/lib/");
         sb.append(getFileHandler().getName(path).replace("&", "&"));
+      }
     }
 
     /**
@@ -217,10 +223,16 @@ private void writeJarPostResource(StringBuilder sb, String path)
      */
     private void writeJarPostResource(Element postResourceEl, String path)
     {
+      if (Boolean.parseBoolean(getPropertyValue(TomcatPropertySet.CONTEXT_MAPJARSTOWEBINFCLASSES))) {
+        postResourceEl.setAttribute("className", JAR_RESOURCE_SET);
+        postResourceEl.setAttribute("base", path.replace("&", "&"));
+        postResourceEl.setAttribute("webAppMount", "/WEB-INF/classes/");
+      } else {
         postResourceEl.setAttribute("className", FILE_RESOURCE_SET);
         postResourceEl.setAttribute("base", path.replace("&", "&"));
         postResourceEl.setAttribute("webAppMount", "/WEB-INF/lib/"
             + getFileHandler().getName(path).replace("&", "&"));
+      }
     }
 
     /**
diff --git a/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/TomcatPropertySet.java b/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/TomcatPropertySet.java
index 4b8f555e49..b2ce6723ef 100644
--- a/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/TomcatPropertySet.java
+++ b/core/containers/tomcat/src/main/java/org/codehaus/cargo/container/tomcat/TomcatPropertySet.java
@@ -54,6 +54,11 @@ public interface TomcatPropertySet
      */
     String CONTEXT_ALLOWWEBJARS = "cargo.tomcat.context.addWebinfClassesResources";
 
+    /**
+     * Whether the contexts for deployed webapplications should map JARs to WEB-INF/classes
+     */
+    String CONTEXT_MAPJARSTOWEBINFCLASSES = "cargo.tomcat.context.mapJarToWebinfClasses";
+
     /**
      * Whether WAR deployables should be copied or referenced.
      */