Must issue a STARTTLS command

Question

I am trying to send error email through log4j. by using following appender:

 <appender name="ERROR_MAIL" class="org.apache.log4j.net.SMTPAppender">
   <param name="SMTPUsername" value="[email protected]" />
    <param name="SMTPPassword" value="**********" />
    <param name="To" value="[email protected]"/>
    <param name="From" value="[email protected]"/>
    <param name="Subject" value="Newyse Error "/>
    <param name="SMTPHost" value="smtp.gmail.com"/>
    <param name="SMTPPort" value="25" />
    <param name="BufferSize" value="10"/>
    <layout class="org.apache.log4j.PatternLayout">
      <param name="ConversionPattern" value="[%d{ISO8601} %t %5p %c:$L]"/>
    </layout>
    <filter class="org.apache.log4j.varia.LevelRangeFilter">
      <param name="LevelMin" value="ERROR"/>
      <param name="LevelMax" value="FATAL"/>
    </filter>
  </appender>   

but I am getting the following exception

com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. wr9sm43519864pbc.7 - gsmtp

from several other question I understood that I need to add the following property in the smtpAppender

props.put("mail.smtp.starttls.enable", "true");

So how we can add it to the existing SMTPAppender ?

Glacier

Answer 1

Many Thanks to @Jk1 to give me the answer that lands me to get the working code with configuration mentioned in the question.

import java.util.Date;
import java.util.Properties;

import javax.mail.Authenticator;
import javax.mail.Message;
import javax.mail.MessagingException;
import javax.mail.Multipart;
import javax.mail.PasswordAuthentication;
import javax.mail.Session;
import javax.mail.internet.MimeBodyPart;
import javax.mail.internet.MimeMultipart;

import org.apache.log4j.Layout;
import org.apache.log4j.helpers.LogLog;
import org.apache.log4j.net.SMTPAppender;
import org.apache.log4j.spi.LoggingEvent;

import com.sun.mail.smtp.SMTPTransport;

/**
 * Extension of Log4j {@link SMTPAppender} for Gmail support
 * 
 */
public class SecureSMTPAppender extends SMTPAppender
{
  /**
   * Cached session for later use i.e. while sending emails
   */
  protected Session session;

  public SecureSMTPAppender()
  {
    super();
  }

  /**
   * Create mail session.
   * 
   * @return mail session, may not be null.
   */
  protected Session createSession()
  {
    Properties props = new Properties();
    props.put("mail.smtps.host", getSMTPHost());
    props.put("mail.smtps.auth", "true");

    Authenticator auth = null;
    if (getSMTPPassword() != null && getSMTPUsername() != null)
    {
      auth = new Authenticator()
      {
        protected PasswordAuthentication getPasswordAuthentication()
        {
          return new PasswordAuthentication(getSMTPUsername(), getSMTPPassword());
        }
      };
    }
    session = Session.getInstance(props, auth);
    if (getSMTPDebug())
    {
      session.setDebug(getSMTPDebug());
    }
    return session;
  }

  /**
   * Send the contents of the cyclic buffer as an e-mail message.
   */
  protected void sendBuffer()
  {
    try
    {
      MimeBodyPart part = new MimeBodyPart();

      StringBuffer sbuf = new StringBuffer();
      String t = layout.getHeader();
      if (t != null)
        sbuf.append(t);
      int len = cb.length();
      for (int i = 0; i < len; i++)
      {
        LoggingEvent event = cb.get();
        sbuf.append(layout.format(event));
        if (layout.ignoresThrowable())
        {
          String[] s = event.getThrowableStrRep();
          if (s != null)
          {
            for (int j = 0; j < s.length; j++)
            {
              sbuf.append(s[j]);
              sbuf.append(Layout.LINE_SEP);
            }
          }
        }
      }

      t = layout.getFooter();
      if (t != null)
        sbuf.append(t);
      part.setContent(sbuf.toString(), layout.getContentType());

      Multipart mp = new MimeMultipart();
      mp.addBodyPart(part);
      msg.setContent(mp);

      msg.setSentDate(new Date());
      send(msg);
    } catch (Exception e)
    {
      LogLog.error("Error occured while sending e-mail notification.", e);
    }
  }

  /**
   * Pulled email send stuff i.e. Transport.send()/Transport.sendMessage(). So
   * that on required this logic can be enhanced.
   * 
   * @param msg
   *          Email Message
   * @throws MessagingException
   */
  protected void send(Message msg) throws MessagingException
  {
    SMTPTransport t = (SMTPTransport) session.getTransport("smtps");
    try
    {
      t.connect(getSMTPHost(), getSMTPUsername(), getSMTPPassword());
      t.sendMessage(msg, msg.getAllRecipients());
    } finally
    {
      System.out.println("Response: " + t.getLastServerResponse());
      t.close();
    }
  }
}

Glacier

Someone takes the time to answer you, and then, not only you take his answer to fix your issue but you also add an answer, based on his, and then accept your own answer? Dude, that's bs... I'd be piiiiiiissed... – Solidus

@gaurav So? what should I do now? – Glacier

Answer 2

First way: you may extend SMTP appender and override createSession() method, where you can add any additional properties to Java Mail session, like aforementioned "mail.smtp.starttls.enable"

public class SecureSMTPAppender extends SMTPAppender {

    private boolean useStartTLS;

    public void setUseStartTLS(boolean useStartTLS) {
        this.useStartTLS = useStartTLS;
    }

    @Override
    protected Session createSession() {
        Properties props = null;
        try {
            props = new Properties(System.getProperties());
        } catch (SecurityException ex) {
            props = new Properties();
        }
        if (getSMTPHost() != null) {
            props.put("mail.smtp.host", getSMTPHost());
        }
        if (useStartTLS) {
            props.put("mail.smtp.starttls.enable", "true");
        }
        Authenticator auth = null;
        if (getSMTPPassword() != null && getSMTPUsername() != null) {
            props.put("mail.smtp.auth", "true");
            auth = new Authenticator() {
                protected PasswordAuthentication getPasswordAuthentication() {
                    return new PasswordAuthentication(getSMTPUsername(), getSMTPPassword());
                }
            };
        }
        Session session = Session.getInstance(props, auth);
        if (getSMTPDebug()) {
            session.setDebug(true);
        }
        return session;
    }
}

Second way: you may start your Java process with an option -Dmail.smtp.starttls.enable=true. This approach looks easier, but requires a control over JVM options; it also may be broken by too retrictive SecurityManager.

Schrick

Thanks for this, is it not possible to set this property from the xml config file? – Nil

SMTPAppender is fairly primitive and does not support tls-related configuration via log4j.xml or log4j.properties. – Schrick