package com.hubspot.singularity.smtp;

import com.google.common.collect.ImmutableMap;
import com.google.common.collect.Lists;
import com.google.common.util.concurrent.MoreExecutors;
import com.google.inject.Inject;
import com.hubspot.mesos.JavaUtils;
import com.hubspot.singularity.config.SMTPConfiguration;
import com.hubspot.singularity.sentry.SingularityExceptionNotifier;
import io.dropwizard.lifecycle.Managed;
import java.util.Arrays;
import java.util.List;
import java.util.Optional;
import java.util.Properties;
import java.util.concurrent.ThreadPoolExecutor;
import java.util.concurrent.TimeUnit;
import javax.inject.Singleton;
import javax.mail.Address;
import javax.mail.Message.RecipientType;
import javax.mail.Session;
import javax.mail.Transport;
import javax.mail.internet.AddressException;
import javax.mail.internet.InternetAddress;
import javax.mail.internet.MimeMessage;
import javax.mail.internet.MimeUtility;
import org.slf4j.Logger;
import org.slf4j.LoggerFactory;

@Singleton
public class SingularitySmtpSender implements Managed {
  private static final Logger LOG = LoggerFactory.getLogger(SingularitySmtpSender.class);

  private final Optional<SMTPConfiguration> maybeSmtpConfiguration;
  private final Optional<ThreadPoolExecutor> mailSenderExecutorService;
  private final SingularityExceptionNotifier exceptionNotifier;

  @Inject
  public SingularitySmtpSender(
    Optional<SMTPConfiguration> maybeSmtpConfiguration,
    SingularityExceptionNotifier exceptionNotifier
  ) {
    this.maybeSmtpConfiguration = maybeSmtpConfiguration;
    this.exceptionNotifier = exceptionNotifier;

    if (maybeSmtpConfiguration.isPresent()) {
      this.mailSenderExecutorService =
        Optional.of(
          JavaUtils.newFixedTimingOutThreadPool(
            maybeSmtpConfiguration.get().getMailMaxThreads(),
            TimeUnit.SECONDS.toMillis(1),
            "SingularitySMTPSender-%d"
          )
        );
    } else {
      this.mailSenderExecutorService = Optional.empty();
    }
  }

  @Override
  public void start() {}

  @Override
  public void stop() {
    if (mailSenderExecutorService.isPresent()) {
      MoreExecutors.shutdownAndAwaitTermination(
        mailSenderExecutorService.get(),
        1,
        TimeUnit.SECONDS
      );
    }
  }

  public void queueMail(
    final List<String> toList,
    final List<String> ccList,
    final String subject,
    final String body
  ) {
    if (toList.isEmpty()) {
      LOG.warn("Couldn't queue email {} because no to address is present", subject);
      return;
    }

    if (!mailSenderExecutorService.isPresent()) {
      LOG.warn(
        String.format(
          "Couldn't queue email %s because no SMTP configuration is present",
          getEmailLogFormat(toList, subject)
        )
      );
      return;
    }

    final String realSubject = maybeSmtpConfiguration.isPresent() &&
      maybeSmtpConfiguration.get().getSubjectPrefix().isPresent()
      ? maybeSmtpConfiguration.get().getSubjectPrefix().get() + subject
      : subject;

    LOG.debug("Queuing an email to {}/{} (subject: {})", toList, ccList, realSubject);

    mailSenderExecutorService
      .get()
      .submit(() -> sendMail(toList, ccList, realSubject, body));
  }

  private String getEmailLogFormat(List<String> toList, String subject) {
    return String.format("[to: %s, subject: %s]", toList, subject);
  }

  private Session createSession(SMTPConfiguration smtpConfiguration, boolean useAuth) {
    Properties properties = System.getProperties();

    properties.setProperty("mail.smtp.host", smtpConfiguration.getHost());
    properties.setProperty(
      "mail.smtp.port",
      Integer.toString(smtpConfiguration.getPort())
    );

    if (smtpConfiguration.isSsl()) {
      properties.setProperty("mail.smtp.ssl.enable", "true");
    }

    if (useAuth) {
      properties.setProperty("mail.smtp.auth", "true");
      return Session.getInstance(
        properties,
        new SMTPAuthenticator(
          smtpConfiguration.getUsername().get(),
          smtpConfiguration.getPassword().get()
        )
      );
    } else {
      return Session.getInstance(properties);
    }
  }

  private void sendMail(
    List<String> toList,
    List<String> ccList,
    String subject,
    String body
  ) {
    final SMTPConfiguration smtpConfiguration = maybeSmtpConfiguration.get();

    boolean useAuth = false;

    if (
      smtpConfiguration.getUsername().isPresent() &&
      smtpConfiguration.getPassword().isPresent()
    ) {
      useAuth = true;
    } else if (
      smtpConfiguration.getUsername().isPresent() ||
      smtpConfiguration.getPassword().isPresent()
    ) {
      LOG.warn(
        "Not using smtp authentication because username ({}) or password ({}) was not present",
        smtpConfiguration.getUsername().isPresent(),
        smtpConfiguration.getPassword().isPresent()
      );
    }

    try {
      final Session session = createSession(smtpConfiguration, useAuth);

      MimeMessage message = new MimeMessage(session);

      Address[] toArray = getAddresses(toList);
      message.addRecipients(RecipientType.TO, toArray);

      if (!ccList.isEmpty()) {
        Address[] ccArray = getAddresses(ccList);
        message.addRecipients(RecipientType.CC, ccArray);
      }

      message.setFrom(new InternetAddress(smtpConfiguration.getFrom()));

      message.setSubject(MimeUtility.encodeText(subject, "utf-8", null));
      message.setContent(body, "text/html; charset=utf-8");

      LOG.trace(
        "Sending a message to {} - {}",
        Arrays.toString(toArray),
        getEmailLogFormat(toList, subject)
      );

      Transport.send(message);
    } catch (Throwable t) {
      LOG.warn("Unable to send message {}", getEmailLogFormat(toList, subject), t);
      exceptionNotifier.notify(
        String.format("Unable to send message (%s)", t.getMessage()),
        t,
        ImmutableMap.of("subject", subject)
      );
    }
  }

  private Address[] getAddresses(List<String> toList) {
    List<InternetAddress> addresses = Lists.newArrayListWithCapacity(toList.size());

    for (String to : toList) {
      try {
        addresses.add(new InternetAddress(to));
      } catch (AddressException t) {
        LOG.warn("Invalid address {} - ignoring", to, t);
      }
    }

    return addresses.toArray(new InternetAddress[addresses.size()]);
  }
}

@@ -3805,24 +3805,139 @@
 rue%22);%0A    %7D
+%0A    if (smtpConfiguration.isStartTLS()) %7B%0A      properties.setProperty(%22mail.smtp.starttls.enable%22, %22true%22);%0A    %7D
 %0A%0A    if (us

Update SingularitySmtpSender.java