Can't send mail via SSL or TLS using SMTP using Javamail

Question

Happy New Year!

I'm working on a application where the user gets an email whenever a particular trigger occurs.

This is the function that I'm using to send Email:

public static void sendEmail(String host, String port, String useSSL, String useTLS, String useAuth, String user, String password, String subject, String content, String type, String recipients)
            throws NoSuchProviderException, AddressException, MessagingException  {
        final Properties props = new Properties();
        props.setProperty("mail.transport.protocol", "smtp");
        props.setProperty("mail.smtp.host", host);
        props.setProperty("mail.smtp.port", port);        
        if (useSSL != null && !useSSL.equals("false") && useSSL.equals("true")) {
            props.setProperty("mail.smtp.ssl.enable", useSSL);
            props.setProperty("mail.smtp.socketFactory.class",
                    "javax.net.ssl.SSLSocketFactory");
            props.setProperty("mail.smtp.socketFactory.port", port);

        }
        if (useTLS != null && !useTLS.equals("false") && useTLS.equals("true")) {
            props.setProperty("mail.smtp.starttls.enable", useTLS);
            props.setProperty("mail.smtp.socketFactory.fallback", "true");
        }   
        props.setProperty("mail.smtp.auth", useAuth);
        props.setProperty("mail.from", user);  
        props.setProperty("mail.smtp.user", user);
        props.setProperty("mail.password", password);

        Session mailSession = Session.getDefaultInstance(props, new Authenticator() {
            protected PasswordAuthentication getPasswordAuthentication() {
                return new PasswordAuthentication(props.getProperty("mail.smtp.user"), props
                        .getProperty("mail.password"));
            }
        });   

        Transport transport = mailSession.getTransport();

        MimeMessage message = new MimeMessage(mailSession);
        message.setHeader("Subject", subject);
        message.setContent(content, type);

        StringTokenizer tokenizer = new StringTokenizer(recipients, ";");
        while (tokenizer.hasMoreTokens()) {
            String recipient = tokenizer.nextToken();
            message.addRecipient(Message.RecipientType.TO,
                    new InternetAddress(recipient));
        }

        transport.connect();
        transport.sendMessage(message, message.getRecipients(Message.RecipientType.TO));
        transport.close();

Odd enough, whenever I try to run the above code with main method it'd send the email for both SSL and TLS protocols successfully.

public static void main(String args[])
    {
        try {
            Notifier.sendEmail("smtp.gmail.com", "587", "false", "true", "true","[email protected]", "testpassword", "CHECKING SETTINGS", "CHECKING EMAIL FUNCTIONALITY", "text/html", "[email protected]");
        } catch (Exception ex) {
            ex.printStackTrace();
        } 
    }

But it fails whenever I try to run the same code through my web application.

Sending it via SSL throws this error:

com.sun.mail.smtp.SMTPSendFailedException: 530-5.5.1 Authentication Required. Learn more at
jvm 1    | 530 5.5.1  https://support.google.com/mail/answer/14257 f12sm88286300pat.20 - gsmtp
jvm 1    | 
jvm 1    |  at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2057)

Sending it via TLS throws this error:

javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587;
jvm 1    |   nested exception is:
jvm 1    |  javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
jvm 1    |  at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1934)

Any kind of help is appreciated.

EDIT1:

Here's the tpl file from front end

<div class="label1"><h3 class="label">Host:</h3></div>
     <div class="field1"><input type="text" class="input1" name="host" size="20" value="$HOST$"></div>
         <div class="port"><h3 class="label">Port:</h3></div>
         <div class="fieldport"><input type="text" class="fieldport" name="port" size="5" value="$PORT$"></div>
         <div class="ssl">
                <input type="radio" name="sslEnable" value="$SSLENABLE$">
                    Enable SSL?
         </div>
         <div class="tls">
                <input type="radio" name="tlsEnable" value="$TLSENABLE$">
                    Enable TLS?
         </div>
         <div class="auth">
                <input type="checkbox" name="auth"$AUTH$>
                    Enable Authentication?
         </div>            
     <div class="label2"><h3 class="label">User:</h3></div>
     <div class="field2"><input type="text" class="input1" name="user" size="20" value="$USER$"></div>
     <div class="label3"><h3 class="label">Password:</h3></div>
     <div class="field3"><input type="password" class="input1" name="password" size="20" value="$PASSWORD$"></div>
     <div class="label4"><h3 class="label">Recipient(s):</h3></div>
     <div class="field4"><input type="text" class="input1" name="recipients" size="50" value="$RECIPIENTS$"></div>

The values gets saved in a configuration file which looks like this:

host=smtp.gmail.com
port=587
ssl=false
tls=true
auth=true
[email protected]
password=O0UbYboDfVFRaiA=
[email protected]
trigger1=false
attempt=0
trigger2=false
percent=5
anyOrAll=ANY
trigger3=true
format=HTML
trigger4=true
trigger5=true

EDIT2:

public static void sendEmail(String message)
      throws NoSuchProviderException, AddressException, MessagingException
  {
    if (message == null || message.trim().equals("")) return;

    StringBuffer content = new StringBuffer();
    content.append(getHeader());
    content.append(message);
    content.append(getFooter());
    String format = NotifyProps.getFormat();
    String type = "text/plain";
    if (format.equals(NotifyProps.HTML)) type = "text/html";

    sendEmail(NotifyProps.getHost(), NotifyProps.getPort(), Boolean.toString(NotifyProps.getUseAuth()), Boolean.toString(NotifyProps.getUseSSL()), Boolean.toString(NotifyProps.getUseTLS()),NotifyProps.getUser(), NotifyProps.getPassword(),
              "Transaction Processor Auto Notification", content.toString(), type,
              NotifyProps.getRecipients())
  }

This is the the class that sets and gets the properties:

https://codeshare.io/5G8ki

Thank you.

Answer 1

Altough your code looks ok, there is at least one big problem. You are trying to use the same port (587) for both TLS and SSL. I am not sure about TLS, but the SSL code should work IF you would send your request to port 465. As written here (google FAQ):

configuring your SMTP server on port 465 (with SSL) and port 587 (with TLS)[...]

They have their own specific ports. The error you get for SSL:

Unrecognized SSL message, plaintext connection?

Is your client not understanding the fact that it received a non-SSL encoded response (due to the TLS port not implementing SSL).

Answer 2

We are having few more properties set for TLS

props.put("mail.smtp.starttls.enable", "true");
props.setProperty("mail.smtp.ssl.enable", "true");
props.setProperty("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
props.put("mail.smtp.socketFactory.fallback", "false");

For Auth use smtps instead of smtp

props.setProperty("mail.smtps.auth", useAuth);

While Getting the Transport

session.getTransport("smtps"); 

Again pass the host email and password while connecting

transport.connect("smtp.gmail.com", "user@email", "password");

For debugging

session.setDebug(true);