[logback-user] SMTPAppender on windows host can't connect to Amazon AWS smtps server

Olexandr Demura oleksander.demura at gmail.com
Thu May 4 07:39:12 CEST 2017

Hi, guys.

I had problem sending error mail notifications on amazon aws windows
while regular mail was fine and linux instance (w\ newer tomcat as well)
was fine.

Since I already had my own Suspendable- and Batching- extensions of
I changed Session and Transport handling to overcome it, see introduced
methods below.
But I wonder if I missed something which could be done thru config.
Options I use are

protected void put(Properties props, String key, String value) {
    if (value != null) {
        String key1 = !isSSL() ? key : key.replace(".smtp.", ".smtps.");
        props.put(key1, value);
protected Session rebuildSessionFromProperties() {
    Properties props = new Properties(OptionHelper.getSystemProperties());
    put(props, "mail.smtp.localhost", getLocalhost());
    if (isSTARTTLS() && isSSL()) {
        addError("Both SSL and StartTLS cannot be enabled simultaneously");
    } else if (isSTARTTLS()) {
        props.put("mail.smtp.starttls.enable", "true");
    } else if (isSSL()) {
        props.put("mail.smtps.ssl.enable", "true");
    return Session.getInstance(props);

protected void sendMessage(MimeMessage mimeMsg)
        throws MessagingException {
    addInfo("About to send out SMTP message \"" + mimeMsg.getSubject()
        + "\" to " + Arrays.asList(mimeMsg.getAllRecipients()));
    Transport transport = session.getTransport(isSSL() ? "smtps" : "smtp");
    if (getUsername() == null) {
    } else if (getSmtpHost() == null) {
        transport.connect(getUsername(), getPassword());
    } else {
        transport.connect(getSmtpHost(), getSmtpPort(), getUsername(),
    try {
        transport.sendMessage(mimeMsg, mimeMsg.getAllRecipients());
    } finally {
        if (transport.isConnected()) {
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