Hi, guys. I had problem sending error mail notifications on amazon aws windows instance, 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 SMTPAppender, 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 <SSL>true</SSL> <smtpHost>email-smtp.eu-west-1.amazonaws.com</smtpHost> <smtpPort>465</smtpPort> <username>...</username> <password>...</password> <from>...</from> <to>...</to> 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())); mimeMsg.saveChanges(); Transport transport = session.getTransport(isSSL() ? "smtps" : "smtp"); if (getUsername() == null) { transport.connect(); } else if (getSmtpHost() == null) { transport.connect(getUsername(), getPassword()); } else { transport.connect(getSmtpHost(), getSmtpPort(), getUsername(), getPassword()); } try { transport.sendMessage(mimeMsg, mimeMsg.getAllRecipients()); } finally { if (transport.isConnected()) { transport.close(); } } }