diff --git a/artemis-server/src/main/java/org/apache/activemq/artemis/spi/core/security/ActiveMQJAASSecurityManager.java b/artemis-server/src/main/java/org/apache/activemq/artemis/spi/core/security/ActiveMQJAASSecurityManager.java
index 26c88b27c2..973ea9691c 100644
--- a/artemis-server/src/main/java/org/apache/activemq/artemis/spi/core/security/ActiveMQJAASSecurityManager.java
+++ b/artemis-server/src/main/java/org/apache/activemq/artemis/spi/core/security/ActiveMQJAASSecurityManager.java
@@ -177,13 +177,24 @@ public class ActiveMQJAASSecurityManager implements ActiveMQSecurityManager3 {
                                            final String password,
                                            final X509Certificate[] certificates) throws LoginException {
       LoginContext lc;
-      if (certificateConfigurationName != null && certificateConfigurationName.length() > 0 && certificates != null) {
-         lc = new LoginContext(certificateConfigurationName, null, new JaasCallbackHandler(user, password, certificates), certificateConfiguration);
-      } else {
-         lc = new LoginContext(configurationName, null, new JaasCallbackHandler(user, password, certificates), configuration);
+      ClassLoader currentLoader = Thread.currentThread().getContextClassLoader();
+      ClassLoader thisLoader = this.getClass().getClassLoader();
+      try {
+         if (thisLoader != currentLoader) {
+            Thread.currentThread().setContextClassLoader(thisLoader);
+         }
+         if (certificateConfigurationName != null && certificateConfigurationName.length() > 0 && certificates != null) {
+            lc = new LoginContext(certificateConfigurationName, null, new JaasCallbackHandler(user, password, certificates), certificateConfiguration);
+         } else {
+            lc = new LoginContext(configurationName, null, new JaasCallbackHandler(user, password, certificates), configuration);
+         }
+         lc.login();
+         return lc.getSubject();
+      } finally {
+         if (thisLoader != currentLoader) {
+            Thread.currentThread().setContextClassLoader(currentLoader);
+         }
       }
-      lc.login();
-      return lc.getSubject();
    }
 
    private Set<RolePrincipal> getPrincipalsInRole(final CheckType checkType, final Set<Role> roles) {
diff --git a/artemis-server/src/test/java/org/apache/activemq/artemis/core/security/jaas/JAASSecurityManagerTest.java b/artemis-server/src/test/java/org/apache/activemq/artemis/core/security/jaas/JAASSecurityManagerTest.java
new file mode 100644
index 0000000000..6707ad2f51
--- /dev/null
+++ b/artemis-server/src/test/java/org/apache/activemq/artemis/core/security/jaas/JAASSecurityManagerTest.java
@@ -0,0 +1,99 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one or more
+ * contributor license agreements. See the NOTICE file distributed with
+ * this work for additional information regarding copyright ownership.
+ * The ASF licenses this file to You under the Apache License, Version 2.0
+ * (the "License"); you may not use this file except in compliance with
+ * the License. You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.apache.activemq.artemis.core.security.jaas;
+
+import org.apache.activemq.artemis.core.security.CheckType;
+import org.apache.activemq.artemis.core.security.Role;
+import org.apache.activemq.artemis.spi.core.security.ActiveMQJAASSecurityManager;
+import org.junit.Rule;
+import org.junit.Test;
+import org.junit.rules.TemporaryFolder;
+import org.junit.runner.RunWith;
+import org.junit.runners.Parameterized;
+
+import java.io.UnsupportedEncodingException;
+import java.net.URL;
+import java.net.URLClassLoader;
+import java.net.URLDecoder;
+import java.nio.charset.StandardCharsets;
+import java.util.Arrays;
+import java.util.Collection;
+import java.util.HashSet;
+import java.util.Set;
+
+import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertNotNull;
+
+@RunWith(Parameterized.class)
+public class JAASSecurityManagerTest {
+
+   @Parameterized.Parameters(name = "newLoader=({0})")
+   public static Collection<Object[]> data() {
+      return Arrays.asList(new Object[][] {{true}, {false}});
+   }
+
+   static {
+      String path = System.getProperty("java.security.auth.login.config");
+      if (path == null) {
+         URL resource = PropertiesLoginModuleTest.class.getClassLoader().getResource("login.config");
+         if (resource != null) {
+            try {
+               path = URLDecoder.decode(resource.getFile(), StandardCharsets.UTF_8.name());
+               System.setProperty("java.security.auth.login.config", path);
+            } catch (UnsupportedEncodingException e) {
+               throw new RuntimeException(e);
+            }
+         }
+      }
+   }
+
+   @Parameterized.Parameter
+   public boolean usingNewLoader;
+
+   @Rule
+   public TemporaryFolder tmpDir = new TemporaryFolder();
+
+   @Test
+   public void testLoginClassloading() throws Exception {
+      ClassLoader existingLoader = Thread.currentThread().getContextClassLoader();
+      System.out.println("loader: " + existingLoader);
+      try {
+         if (usingNewLoader) {
+            URLClassLoader simulatedLoader = new URLClassLoader(new URL[]{tmpDir.getRoot().toURI().toURL()}, null);
+            Thread.currentThread().setContextClassLoader(simulatedLoader);
+         }
+         ActiveMQJAASSecurityManager securityManager = new ActiveMQJAASSecurityManager("PropertiesLogin");
+
+         String result = securityManager.validateUser("first", "secret", null);
+
+         assertNotNull(result);
+         assertEquals("first", result);
+
+         Role role = new Role("programmers", true, true, true, true, true, true, true, true, true, true);
+         Set<Role> roles = new HashSet<>();
+         roles.add(role);
+         result = securityManager.validateUserAndRole("first", "secret", roles, CheckType.SEND, "someaddress", null);
+
+         assertNotNull(result);
+         assertEquals("first", result);
+
+      } finally {
+         Thread.currentThread().setContextClassLoader(existingLoader);
+      }
+   }
+
+}