Must issue a STARTTLS command first. Sending email with Java and Google Apps

Question

I am trying to use Bill the Lizard\'s code to send an email using Google Apps. I am getting this error:

Exception in thread \"main\" javax.mail.SendFailedEx         


        

Answer 1

This was driving me crazy and so just wanted to add what worked for me. I had to update my version of JavaMail (1.4.5) for this to work - not sure what version was being used before.

Once I updated to new version of JavaMail, the following code worked for me (can uncomment the debug lines to get additional debugging info - port was 587 and host was smtp.gmail.com):

public void sendMailWithAuth(String host, String user, String password, 
    String port, List toList, String htmlBody, 
        String subject) throws Exception {

    Properties props = System.getProperties();

    props.put("mail.smtp.user",user); 
    props.put("mail.smtp.password", password);
    props.put("mail.smtp.host", host); 
    props.put("mail.smtp.port", port); 
    //props.put("mail.debug", "true"); 
    props.put("mail.smtp.auth", "true"); 
    props.put("mail.smtp.starttls.enable","true"); 
    props.put("mail.smtp.EnableSSL.enable","true");

    Session session = Session.getInstance(props, null);
    //session.setDebug(true);

    MimeMessage message = new MimeMessage(session);
    message.setFrom(new InternetAddress(user));

    // To get the array of addresses
    for (String to: toList) {
        message.addRecipient(Message.RecipientType.TO, new InternetAddress(to));
    }

    message.setSubject(subject);
    message.setContent(htmlBody, "text/html");

    Transport transport = session.getTransport("smtp");
    try {
        transport.connect(host, user, password);
        transport.sendMessage(message, message.getAllRecipients());
    } finally {
        transport.close();
    }
}