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 ?

Answer 1

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.