STARTTLS support?

[Lars-]

Is your feature request related to a problem? Please describe.
I would like to send mails via Office365, but I can't seem to find any documentation on STARTTLS.

Describe the solution you'd like
STARTTLS support or the documentation for it.

Describe alternatives you've considered
Nothing yet, MailDroid is already implemented, so it would be great to keep using it.

Additional context
None

[nedimf]

Sure, I'll add it by end of this week. Happy holidays @Lars-

[nedimf]

Hey @Lars- , checkout latest commit for the feature you requested, let me know if it works.

[Lars-]

Unfortunately, it doesn't work:

E/MessagingException: com.sun.mail.util.MailConnectException: Couldn't connect to host, port: smtp.office365.com, 587; timeout -1;
      nested exception is:
    	java.net.SocketTimeoutException: failed to connect to smtp.office365.com/2603:1026:c03:3030::2 (port 587) after 90000ms

The code that I use:

MaildroidX.Builder maildroidX = new MaildroidX.Builder()
                    .smtp("smtp.office365.com")
                    .smtpUsername("[REDACTED]")
                    .smtpPassword("[REDACTED]")
                    .isStartTLSEnabled(true)
                    .port(String.valueOf(587))
                    .type(MaildroidXType.PLAIN)

                    .to("[REDACTED]")
                    .from("[REDACTED]")
                    .subject("[REDACTED]")
                    .body(body)
                    .onCompleteCallback(new MaildroidX.onCompleteCallback() {
                        @Override
                        public void onSuccess() {
                         // Stuff
                        }

                        @Override
                        public void onFail(String s) {
                            //Stuff
                        }

                        @Override
                        public long getTimeout() {
                            return 5000;
                        }
                    });

When I try it with PHP, it does work. I looked it over a couple of times, but there doesn't seem to be any spelling mistake.
PHP code (using PHPMailer)

        $mail->SMTPDebug = SMTP::DEBUG_OFF;
	$mail->isSMTP();
	$mail->Host       = 'smtp.office365.com';
	$mail->SMTPAuth   = true;
	$mail->Username   = '[REDACTED]';
	$mail->Password   = '[REDACTED]';
	$mail->SMTPSecure = PHPMailer::ENCRYPTION_STARTTLS;
	$mail->Port       = 587;

	$mail->setFrom( '[REDACTED]' );
	$mail->addAddress( '[REDACTED]' );

	foreach ( $files as $file ) {
		$mail->addAttachment( $file );
	}

	$mail->isHTML( false );
	$mail->Subject = $_POST['subject'] ?? '';
	$mail->Body    = $_POST['body'] ?? '';

	$mail->send();

What could the problem possibly be?

[nedimf]

Taking closer look at it, sorry for inconvenience

[Lars-]

I appreciate it, thanks! Maybe reopen the issue until it works?

[nedimf]

Did you check this? Maybe it's firewall issue? Let me know if that is the case.
Issue pointing to MS 365 configuration and this

Microsoft Office 365 issue

[Lars-]

Yep, I checked it. The android app runs on the same network as the PHP script. So that couldn't be the problem.
The only thing that could be it is the verification of the certificate of office365. Maybe that version of Android doesn't know that certificate yet or something like that. Could be tested with a "do not verify certificate" option. I know that isn't safe, but it could explain it.

[nedimf]

Alright, what version of Android is that? @Lars-

[nedimf]

Is issue being resolved? @Lars-

[Lars-]

Sorry, missed your comment. It's running on Android 5.1 and unfortunately not upgradeable.

[nedimf]

I'm pretty sure issue is with 5.1 version it self. So library wise I don't see what can be done. SSL seems to work on other versions. @Lars-

[nedimf]

Concluding this is not Maildroid issue. This issue has been addressed.