diff --git a/webgoat-container/src/main/java/org/owasp/webgoat/plugins/Plugin.java b/webgoat-container/src/main/java/org/owasp/webgoat/plugins/Plugin.java
index 5c57e9139..7cd012d05 100644
--- a/webgoat-container/src/main/java/org/owasp/webgoat/plugins/Plugin.java
+++ b/webgoat-container/src/main/java/org/owasp/webgoat/plugins/Plugin.java
@@ -2,12 +2,12 @@ package org.owasp.webgoat.plugins;
 
 import com.google.common.base.Optional;
 import com.google.common.collect.Lists;
+import org.apache.catalina.loader.WebappClassLoader;
 import org.owasp.webgoat.lessons.AbstractLesson;
 import org.springframework.util.StringUtils;
 
 import java.io.File;
 import java.io.IOException;
-import java.net.URLClassLoader;
 import java.nio.file.Path;
 import java.util.Arrays;
 import java.util.HashMap;
@@ -43,10 +43,10 @@ public class Plugin {
     private void findLesson(String name) {
         String realClassName = StringUtils.trimLeadingCharacter(name, '/').replaceAll("/", ".").replaceAll(".class", "");
         //TODO should be passed in (refactor)
-        URLClassLoader cl = (URLClassLoader) Thread.currentThread().getContextClassLoader();
+        WebappClassLoader cl = (WebappClassLoader) Thread.currentThread().getContextClassLoader();
 
         try {
-            Class clazz = cl.loadClass(realClassName);
+            Class clazz = cl.loadClass(realClassName, true);
 
             if (AbstractLesson.class.isAssignableFrom(clazz)) {
                 this.lesson = clazz;
diff --git a/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginContextListener.java b/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginContextListener.java
new file mode 100644
index 000000000..43e58d07f
--- /dev/null
+++ b/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginContextListener.java
@@ -0,0 +1,36 @@
+package org.owasp.webgoat.plugins;
+
+import javax.servlet.ServletContextEvent;
+import javax.servlet.ServletContextListener;
+import javax.servlet.annotation.WebListener;
+import java.nio.file.Paths;
+
+/**
+ * Created by nanne_000 on 9/29/2015.
+ */
+@WebListener
+public class PluginContextListener implements ServletContextListener {
+    @Override
+    public void contextInitialized(ServletContextEvent event) {
+        String pluginPath = event.getServletContext().getRealPath("plugin_lessons");
+        String targetPath = event.getServletContext().getRealPath("plugin_extracted");
+
+        if (event.getServletContext().getInitParameter("plugins_loaded") == null) {
+            new PluginsLoader(Paths.get(pluginPath), Paths.get(targetPath)).copyJars();
+        }
+        event.getServletContext().setInitParameter("plugins_loaded", "");
+    }
+
+    @Override
+    public void contextDestroyed(ServletContextEvent event) {
+//        String targetPath = event.getServletContext().getRealPath("plugin_extracted");
+//        WebappClassLoader cl = (WebappClassLoader)Thread.currentThread().getContextClassLoader();
+//        cl.closeJARs(true);
+//        Path webInfLib = Paths.get(targetPath).getParent().resolve(cl.getJarPath().replaceFirst("\\/", ""));
+//        try {
+//            FileUtils.cleanDirectory(webInfLib.toFile());
+//        } catch (IOException e) {
+//            e.printStackTrace();
+//        }
+    }
+}
diff --git a/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginsLoader.java b/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginsLoader.java
index b725d9d9f..930ebbf30 100644
--- a/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginsLoader.java
+++ b/webgoat-container/src/main/java/org/owasp/webgoat/plugins/PluginsLoader.java
@@ -13,7 +13,9 @@ import java.net.URL;
 import java.nio.file.FileVisitResult;
 import java.nio.file.Files;
 import java.nio.file.Path;
+import java.nio.file.Paths;
 import java.nio.file.SimpleFileVisitor;
+import java.nio.file.StandardCopyOption;
 import java.nio.file.attribute.BasicFileAttributes;
 import java.util.List;
 import java.util.Objects;
@@ -46,6 +48,25 @@ public class PluginsLoader implements Runnable {
         this.pluginTarget = Objects.requireNonNull(pluginTarget, "plugin target cannot be null");
     }
 
+    public void copyJars() {
+        try {
+            WebappClassLoader cl = (WebappClassLoader) Thread.currentThread().getContextClassLoader();
+            cl.setAntiJARLocking(true);
+
+            List<URL> jars = listJars();
+
+            cl.closeJARs(true);
+            Path webInfLib = pluginTarget.getParent().resolve(cl.getJarPath().replaceFirst("\\/", ""));
+            for (URL jar : jars) {
+                Path sourceJarFile = Paths.get(jar.toURI());
+                Files.copy(sourceJarFile, webInfLib.resolve(sourceJarFile.getFileName()),
+                        StandardCopyOption.REPLACE_EXISTING);
+            }
+        } catch (Exception e) {
+            logger.error("Loading plugins failed", e);
+        }
+    }
+
     /**
      * <p>loadPlugins.</p>
      *
@@ -59,9 +80,6 @@ public class PluginsLoader implements Runnable {
             PluginFileUtils.createDirsIfNotExists(pluginTarget);
             cleanupExtractedPluginsDirectory();
             List<URL> jars = listJars();
-            for (URL url : jars) {
-                cl.addRepository(url.toString());
-            }
 
             plugins = processPlugins(jars);
         } catch (Exception e) {
@@ -71,13 +89,12 @@ public class PluginsLoader implements Runnable {
     }
 
 
-
     private void cleanupExtractedPluginsDirectory() {
         Path i18nDirectory = pluginTarget.resolve("plugin/i18n/");
         FileUtils.deleteQuietly(i18nDirectory.toFile());
     }
 
-    private List<URL> listJars() throws IOException {
+    public List<URL> listJars() throws IOException {
         final List<URL> jars = Lists.newArrayList();
         Files.walkFileTree(pluginSource, new SimpleFileVisitor<Path>() {
 
@@ -127,7 +144,9 @@ public class PluginsLoader implements Runnable {
         return extractorCallables;
     }
 
-    /** {@inheritDoc} */
+    /**
+     * {@inheritDoc}
+     */
     @Override
     public void run() {
         loadPlugins();
diff --git a/webgoat-container/src/main/java/org/owasp/webgoat/service/PluginReloadService.java b/webgoat-container/src/main/java/org/owasp/webgoat/service/PluginReloadService.java
index 9415446cc..83ece5a64 100644
--- a/webgoat-container/src/main/java/org/owasp/webgoat/service/PluginReloadService.java
+++ b/webgoat-container/src/main/java/org/owasp/webgoat/service/PluginReloadService.java
@@ -30,6 +30,7 @@
  */
 package org.owasp.webgoat.service;
 
+import org.owasp.webgoat.plugins.PluginsLoader;
 import org.owasp.webgoat.session.WebSession;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
@@ -40,6 +41,7 @@ import org.springframework.web.bind.annotation.RequestMapping;
 import org.springframework.web.bind.annotation.ResponseBody;
 
 import javax.servlet.http.HttpSession;
+import java.nio.file.Paths;
 
 /**
  * <p>PluginReloadService class.</p>
@@ -61,6 +63,11 @@ public class PluginReloadService extends BaseService {
     public @ResponseBody
     ResponseEntity<String> reloadPlugins(HttpSession session) {
         WebSession webSession = (WebSession) session.getAttribute(WebSession.SESSION);
+        logger.debug("Loading plugins into cache");
+        String pluginPath = session.getServletContext().getRealPath("plugin_lessons");
+        String targetPath = session.getServletContext().getRealPath("plugin_extracted");
+        new PluginsLoader(Paths.get(pluginPath), Paths.get(targetPath)).copyJars();
+
         webSession.getCourse().loadLessonFromPlugin(session.getServletContext());
         return new ResponseEntity("Plugins reload refresh the WebGoat page!",HttpStatus.OK);
     }