Php – Send formated (bold, html, …) Email to Gmail with PHP

Be sure to use System.Net.Mail, not the deprecated System.Web.Mail. Doing SSL with System.Web.Mail is a gross mess of hacky extensions.

using System.Net;
using System.Net.Mail;

var fromAddress = new MailAddress("from@gmail.com", "From Name");
var toAddress = new MailAddress("to@example.com", "To Name");
const string fromPassword = "fromPassword";
const string subject = "Subject";
const string body = "Body";

var smtp = new SmtpClient
{
    Host = "smtp.gmail.com",
    Port = 587,
    EnableSsl = true,
    DeliveryMethod = SmtpDeliveryMethod.Network,
    UseDefaultCredentials = false,
    Credentials = new NetworkCredential(fromAddress.Address, fromPassword)
};
using (var message = new MailMessage(fromAddress, toAddress)
{
    Subject = subject,
    Body = body
})
{
    smtp.Send(message);
}

Additionally go to the Google Account > Security page and look at the Signing in to Google > 2-Step Verification setting.

• If it is enabled, then you have to generate a password allowing .NET to bypass the 2-Step Verification. To do this, click on Signing in to Google > App passwords, select app = Mail, and device = Windows Computer, and finally generate the password. Use the generated password in the fromPassword constant instead of your standard Gmail password.
• If it is disabled, then you have to turn on Less secure app access, which is not recommended! So better enable the 2-Step verification.

First download the JavaMail API and make sure the relevant jar files are in your classpath.

Here's a full working example using GMail.

import java.util.*;
import javax.mail.*;
import javax.mail.internet.*;

public class Main {

    private static String USER_NAME = "*****";  // GMail user name (just the part before "@gmail.com")
    private static String PASSWORD = "********"; // GMail password
    private static String RECIPIENT = "lizard.bill@myschool.edu";

    public static void main(String[] args) {
        String from = USER_NAME;
        String pass = PASSWORD;
        String[] to = { RECIPIENT }; // list of recipient email addresses
        String subject = "Java send mail example";
        String body = "Welcome to JavaMail!";

        sendFromGMail(from, pass, to, subject, body);
    }

    private static void sendFromGMail(String from, String pass, String[] to, String subject, String body) {
        Properties props = System.getProperties();
        String host = "smtp.gmail.com";
        props.put("mail.smtp.starttls.enable", "true");
        props.put("mail.smtp.host", host);
        props.put("mail.smtp.user", from);
        props.put("mail.smtp.password", pass);
        props.put("mail.smtp.port", "587");
        props.put("mail.smtp.auth", "true");

        Session session = Session.getDefaultInstance(props);
        MimeMessage message = new MimeMessage(session);

        try {
            message.setFrom(new InternetAddress(from));
            InternetAddress[] toAddress = new InternetAddress[to.length];

            // To get the array of addresses
            for( int i = 0; i < to.length; i++ ) {
                toAddress[i] = new InternetAddress(to[i]);
            }

            for( int i = 0; i < toAddress.length; i++) {
                message.addRecipient(Message.RecipientType.TO, toAddress[i]);
            }

            message.setSubject(subject);
            message.setText(body);
            Transport transport = session.getTransport("smtp");
            transport.connect(host, from, pass);
            transport.sendMessage(message, message.getAllRecipients());
            transport.close();
        }
        catch (AddressException ae) {
            ae.printStackTrace();
        }
        catch (MessagingException me) {
            me.printStackTrace();
        }
    }
}

Naturally, you'll want to do more in the catch blocks than print the stack trace as I did in the example code above. (Remove the catch blocks to see which method calls from the JavaMail API throw exceptions so you can better see how to properly handle them.)

Thanks to @jodonnel and everyone else who answered. I'm giving him a bounty because his answer led me about 95% of the way to a complete answer.