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Turns out that JavaMail is a bit more frustrating than I thought it would be. I've looked at several examples online on how to send a simple SMTP email through Gmail's servers (but not through SSL). After trying several different examples of code, I keep concluding to the same example exception when I call transport.connect() . I keep getting this stack trace: Exception in thread "main" com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. l10sm302158wfk.21 at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2057) at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1580) at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1097) at SendEmail.main(SendEmail.java:47) Can someone please tell me what I should add or do to fix this? Here is my code: Properties props = new Properties(); props.put("mail.transport.protocol", "smtp"); props.put("mail.host", "smtp.gmail.com"); props.put("mail.user", "blahblah@gmail.com"); props.put("mail.password", "blah"); props.put("mail.port", "587"); Session mailSession = Session.getDefaultInstance(props, null); Transport transport = mailSession.getTransport(); MimeMessage message = new MimeMessage(mailSession); message.setSubject("This is a test"); message.setContent("This is a test", "text/plain"); message.addRecipient(Message.RecipientType.TO, new InternetAddress("blahblah2@gmail.com")); transport.connect(); transport.sendMessage(message, message.getRecipients(Message.RecipientType.TO)); transport.close();

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