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Index: glassfish/appserv-core/src/java/com/sun/enterprise/naming/MailSessionAuthenticator.java
--- glassfish/appserv-core/src/java/com/sun/enterprise/naming/MailSessionAuthenticator.java No Base Revision
+++ glassfish/appserv-core/src/java/com/sun/enterprise/naming/MailSessionAuthenticator.java Locally New
@@ -0,0 +1,69 @@
+/*
+ * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS HEADER.
+ *
+ * Copyright 1997-2009 Sun Microsystems, Inc. All rights reserved.
+ *
+ * The contents of this file are subject to the terms of either the GNU
+ * General Public License Version 2 only ("GPL") or the Common Development
+ * and Distribution License("CDDL") (collectively, the "License").  You
+ * may not use this file except in compliance with the License. You can obtain
+ * a copy of the License at https://glassfish.dev.java.net/public/CDDL+GPL.html
+ * or glassfish/bootstrap/legal/LICENSE.txt.  See the License for the specific
+ * language governing permissions and limitations under the License.
+ *
+ * When distributing the software, include this License Header Notice in each
+ * file and include the License file at glassfish/bootstrap/legal/LICENSE.txt.
+ * Sun designates this particular file as subject to the "Classpath" exception
+ * as provided by Sun in the GPL Version 2 section of the License file that
+ * accompanied this code.  If applicable, add the following below the License
+ * Header, with the fields enclosed by brackets [] replaced by your own
+ * identifying information: "Portions Copyrighted [year]
+ * [name of copyright owner]"
+ *
+ * Contributor(s):
+ *
+ * If you wish your version of this file to be governed by only the CDDL or
+ * only the GPL Version 2, indicate your decision by adding "[Contributor]
+ * elects to include this software in this distribution under the [CDDL or GPL
+ * Version 2] license."  If you don't indicate a single choice of license, a
+ * recipient has the option to distribute your version of this file under
+ * either the CDDL, the GPL Version 2 or to extend the choice of license to
+ * its licensees as provided above.  However, if you add GPL Version 2 code
+ * and therefore, elected the GPL Version 2 license, then the option applies
+ * only if the new code is made subject to such option by the copyright
+ * holder.
+ */
+
+package com.sun.enterprise.naming;
+
+import java.util.Properties;
+import javax.mail.Authenticator;
+import javax.mail.PasswordAuthentication;
+
+/**
+ *
+ * @author peterw99
+ */
+public class MailSessionAuthenticator extends Authenticator {
+
+    private final Properties props;
+
+    public MailSessionAuthenticator(Properties props) {
+        this.props = props;
+    }
+
+    @Override
+    protected PasswordAuthentication getPasswordAuthentication() {
+        PasswordAuthentication authenticator = null;
+        String protocol = getRequestingProtocol();
+        if(protocol != null) {
+            String password = props.getProperty("mail." + protocol + ".password");
+            String username = getDefaultUserName();
+            if(password != null && username != null) {
+                authenticator = new PasswordAuthentication(username, password);
+            }
+        }
+        return authenticator;
+    }
+
+}
Index: glassfish/appserv-core/src/java/com/sun/enterprise/naming/NamingManagerImpl.java
--- glassfish/appserv-core/src/java/com/sun/enterprise/naming/NamingManagerImpl.java Base (1.39.2.1)
+++ glassfish/appserv-core/src/java/com/sun/enterprise/naming/NamingManagerImpl.java Locally Modified (Based On 1.39.2.1)
@@ -1,7 +1,7 @@
 /*
  * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS HEADER.
  * 
- * Copyright 1997-2007 Sun Microsystems, Inc. All rights reserved.
+ * Copyright 1997-2009 Sun Microsystems, Inc. All rights reserved.
  * 
  * The contents of this file are subject to the terms of either the GNU
  * General Public License Version 2 only ("GPL") or the Common Development
@@ -877,8 +877,12 @@
 		
 		// Note: javax.mail.Session is not serializable,
 		// but we need to get a new instance on every lookup.
+                Properties props = config.getMailProperties();
 		javax.mail.Session s = javax.mail.Session.getInstance(
-								      config.getMailProperties(), null);
+                        props, new MailSessionAuthenticator(props));
+                if("smtps".equals(props.getProperty("mail.transport.protocol"))) {
+                    s.setProtocolForAddress("rfc822", "smtps");
+                }
 		s.setDebugOut(new PrintStream(new MailLogOutputStream()));
 		s.setDebug(true);
 		obj = s;