Would you be willing to post your code?  There is no JavaMail SSL/TLS example
on the TomEE examples page.  I did put in a request to add a JavaMail
SSL/TLS example.  Maybe I implemented my code wrong from reading this
thread.
http://tomee-openejb.979440.n4.nabble.com/Not-loading-smtps-resource-properly-td4664442.html#a4664460
 
If you want you can take a look at what I have and see where I go wrong. 
When I use the same set of seven smtp parms on my google account I get the
following error.  At this point I am assuming there is something wrong with
my code.

smtps DEBUG: Successful connection
MAIL FROM: <[email protected]>
530-5.5.1 Authentication Required. Learn more at
org.apache.geronimo.javamail.transport.smtp.SMTPSendFailedException: 5.5.1
Authentication Required. Learn more at

============================================

                // Recipient's email ID needs to be mentioned.
                String to = "[email protected]";
                InternetAddress[] addresses = new InternetAddress[1];
                                ;
                try {
                        addresses[0] = new InternetAddress("[email protected]");
                } catch (AddressException e) {
                        // TODO Auto-generated catch block
                        e.printStackTrace();
                }

                // Sender's email ID needs to be mentioned
                String from = "[email protected]";

                // Assuming you are sending email from localhost
                // String host = "localhost";

                
                properties.setProperty("mail.debug", "true");
                properties.setProperty("mail.transport.protocol", "smtp");
                // properties.setProperty("mail.smtp.socketFactory.class",
"javax.net.ssl.SSLSocketFactory");
                // properties.setProperty("mail.smtp.socketFactory.fallback", 
"false");
                properties.setProperty("mail.smtp.host", "smtp.gmail.com");
                // properties.setProperty("mail.smtp.host", 
"mailout.easydns.com");
                properties.setProperty("mail.smtp.port", "587");
                // properties.setProperty("mail.smtp.port", "465");
                properties.setProperty("mail.smtp.auth", "true");
                properties.setProperty("mail.smtp.starttls.enable", "true");
                // properties.setProperty("mail.smtp.starttls.required", 
"true");
                properties.setProperty("mail.smtp.user", "[email protected]");
                // properties.setProperty("mail.smtp.user", "[email protected]");
                // properties.setProperty("mail.smtp.password", "_mypassword_");
                //properties.setProperty("mail.smtp.password", "_mypassword_");
                // properties.setProperty("user", "[email protected]");
                // properties.setProperty("user", "[email protected]");
                properties.setProperty("password", "_mypassword_");
                // properties.setProperty("password", "_mypassword_");
        
                Session session = Session.getDefaultInstance(properties,
                                new javax.mail.Authenticator() {
                                        protected PasswordAuthentication 
getPasswordAuthentication() {
                                                return new 
PasswordAuthentication(properties.getProperty("user"),
properties.getProperty("password"));
                                        }
                                });             
                
                // Session session = Session.getDefaultInstance(properties);
                System.out.println("mail.debug: " + 
properties.getProperty("mail.debug"));
                System.out.println("mail.transport.protocol: " +
properties.getProperty("mail.transport.protocol"));
                System.out.println("mail.smtp.socketFactory.class: " +
properties.getProperty("mail.smtp.socketFactory.class"));
                System.out.println("mail.smtp.socketFactory.fallback: " +
properties.getProperty("mail.smtp.socketFactory.fallback"));
                System.out.println("mail.smtp.host: " +
properties.getProperty("mail.smtp.host"));
                System.out.println("mail.smtp.port: " +
properties.getProperty("mail.smtp.port"));
                System.out.println("mail.smtp.auth: " +
properties.getProperty("mail.smtp.auth"));
                System.out.println("mail.smtp.user: " +
properties.getProperty("mail.smtp.user"));
                System.out.println("mail.smtp.password: " +
properties.getProperty("mail.smtp.password"));
                System.out.println("mail.smtp.starttls.enable: " +
properties.getProperty("mail.smtp.starttls.enable"));
                System.out.println("mail.smtp.starttls.required: " +
properties.getProperty("mail.smtp.starttls.required"));
                System.out.println("user: " + properties.getProperty("user"));
                System.out.println("password: " + 
properties.getProperty("password"));

                System.out.println("mail.debug: " + 
session.getProperty("mail.debug"));
                System.out.println("mail.transport.protocol: " +
session.getProperty("mail.transport.protocol"));
                System.out.println("mail.smtp.socketFactory.class: " +
session.getProperty("mail.smtp.socketFactory.class"));
                System.out.println("mail.smtp.socketFactory.fallback: " +
session.getProperty("mail.smtp.socketFactory.fallback"));
                System.out.println("mail.smtp.host: " +
session.getProperty("mail.smtp.host"));
                System.out.println("mail.smtp.port: " +
session.getProperty("mail.smtp.port"));
                System.out.println("mail.smtp.auth: " +
session.getProperty("mail.smtp.auth"));
                System.out.println("mail.smtp.user: " +
session.getProperty("mail.smtp.user"));
                System.out.println("mail.smtp.password: " +
session.getProperty("mail.smtp.password"));
                System.out.println("mail.smtp.starttls.enable: " +
session.getProperty("mail.smtp.starttls.enable"));
                System.out.println("mail.smtp.starttls.required: " +
session.getProperty("mail.smtp.starttls.required"));
                System.out.println("user: " + session.getProperty("user"));
                System.out.println("password: " + 
session.getProperty("password"));

                // Set response content type
                response.setContentType("text/html");
                PrintWriter out = response.getWriter();

                try { // Create a default MimeMessage object.
                        SMTPMessage message = new SMTPMessage(session);
                        // MimeMessage message = new MimeMessage(session);

                        // Set From: header field of the header.
                        message.setFrom(new InternetAddress(from));

                        // Set To: header field of the header.
                        message.addRecipient(Message.RecipientType.TO, new 
InternetAddress(to));

                        // Set Subject: header field
                        message.setSubject("This is the Subject Line!");

                        // Create the message part
                        BodyPart messageBodyPart = new MimeBodyPart();

                        // Fill the message messageBodyPart.setText("This is 
message body");

                        // Create a multipart message
                        Multipart multipart = new MimeMultipart();

                        // Set text message part 
multipart.addBodyPart(messageBodyPart);

                        // Part two is attachment messageBodyPart = new 
MimeBodyPart();
                        String filename = "file.txt";
                        DataSource source = new FileDataSource(filename);
                        messageBodyPart.setDataHandler(new DataHandler(source));
                        messageBodyPart.setFileName(filename);
                        multipart.addBodyPart(messageBodyPart);
                        
                        SMTPSTransport smtpT = new SMTPSTransport(session, new
URLName(session.getProperty("mail.smtp.host")));
                        smtpT.connect(session.getProperty("mail.smtp.host"),
session.getProperty("mail.smtp.user"),
session.getProperty("mail.smtp.password"));
                        smtpT.sendMessage(message, addresses);                  

                        // Send the complete message parts 
message.setContent(multipart );

                        // Send message
                        Transport.send(message);
                        String title = "Send Email";
                        String res = "Sent message successfully....";
                        String docType = "<!doctype html public 
\&quot;-//w3c//dtd html 4.0
&quot; + &quot;transitional//en\&quot;>\n";
                        out.println(docType + "<html>\n" + "<head><title>" + 
title +
"</title></head>\n"
                                        + "<body bgcolor=\"#f0f0f0\">\n" + "
" + title + "
\n"
                                        + "<p align=\"center\">" + res + 
"</p>\n" + "</body></html>");
                } catch (MessagingException mex) {
                        mex.printStackTrace();
                }

        }






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