I would like to send SMTPS mail via TLSv1.2/TLSv1.3 on port 587.
I use Axigen as a mail server, with the following configuration:
- listeners ssl : 465 / 587
- ssl configuration : TLS 1.2 / TLS 1.3
EXAMPLE WITH PORT 587
Here is the java debug trail :
DEBUG SMTP: need username and password for authentication
DEBUG SMTP: protocolConnect returning false, host=192.168.59.99, user="user", password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "192.168.59.99", port 587, isSSL true
220 axigen Axigen ESMTP ready
DEBUG SMTP: connected to host "192.168.59.99", port: 587
EHLO "DOMAIN"
250-axigen Axigen ESMTP hello
...
DEBUG SMTP: STARTTLS requested but already using SSL
DEBUG SMTP: protocolConnect login, host=192.168.59.99, user=jacques.durand@ca.lan, password=<non-null>
DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2
DEBUG SMTP: Using mechanism LOGIN
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN succeeded
DEBUG SMTP: use8bit false
MAIL FROM:<jacques.durand@ca.lan>
250 Sender accepted
RCPT TO:<jacques.durand@ca.lan>
250 Recipient accepted
DEBUG SMTP: Verified Addresses
DEBUG SMTP: jacques.durand@ca.lan
DATA
354 Ready to receive data; remember <CRLF>.<CRLF>
Date: Tue, 7 Feb 2023 10:03:25 +0100 (CET)
From: jacques.durand@ca.lan
To: jacques.durand@ca.lan
Message-ID: <947679291.0.1675760605998@192.168.59.99>
Subject: TestMail
MIME-Version: 1.0
Content-Type: text/plain; charset=us-ascii
Content-Transfer-Encoding: 7bit
TestMail
.
250 Mail queued for delivery
DEBUG SMTP: message successfully delivered to mail server
QUIT
221-axigen Axigen ESMTP is closing connection
221 Good bye
Process finished with exit code 0
I use wireshark to see the exchanges on the mail server.
On port 587 the protocol used is TCP/SMTP, but it is not SMTPS.
EXAMPLE WITH PORT 465
Java debug trail :
DEBUG SMTP: need username and password for authentication
DEBUG SMTP: protocolConnect returning false, host=192.168.59.99, user="user", password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "192.168.59.99", port 465, isSSL true
220 axigen Axigen ESMTP ready
DEBUG SMTP: connected to host "192.168.59.99", port: 465
EHLO "DOMAIN"
250-axigen Axigen ESMTP hello
...
DEBUG SMTP: STARTTLS requested but already using SSL
DEBUG SMTP: protocolConnect login, host=192.168.59.99, user=jacques.durand@ca.lan, password=<non-null>
DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2
DEBUG SMTP: Using mechanism LOGIN
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN succeeded
DEBUG SMTP: use8bit false
MAIL FROM:<jacques.durand@ca.lan>
250 Sender accepted
RCPT TO:<jacques.durand@ca.lan>
250 Recipient accepted
DEBUG SMTP: Verified Addresses
DEBUG SMTP: jacques.durand@ca.lan
DATA
354 Ready to receive data; remember <CRLF>.<CRLF>
Date: Tue, 7 Feb 2023 10:58:52 +0100 (CET)
From: jacques.durand@ca.lan
To: jacques.durand@ca.lan
Message-ID: <947679291.0.1675763932670@192.168.59.99>
Subject: TestMail
MIME-Version: 1.0
Content-Type: text/plain; charset=us-ascii
Content-Transfer-Encoding: 7bit
TestMail
.
250 Mail queued for delivery
DEBUG SMTP: message successfully delivered to mail server
QUIT
221-axigen Axigen ESMTP is closing connection
221 Good bye
Process finished with exit code 0
On wireshark with port 465, we can see that the protocol used is TLSv1.3.
Below is the Java code for sending mail : (I have used all combinations of java smtp/smtps properties without success)
import com.sun.mail.smtp.SMTPTransport;
import jakarta.mail.*;
import jakarta.mail.internet.InternetAddress;
import jakarta.mail.internet.MimeBodyPart;
import jakarta.mail.internet.MimeMessage;
import jakarta.mail.internet.MimeMultipart;
public class SendMail {
public static void main(String[] args) throws MessagingException {
Session session = null;
Properties properties = System.getProperties();
properties.put("mail.debug", "true");
properties.put("mail.transport.protocol", "smtp");
properties.put("mail.host", "192.168.59.99");
properties.put("mail.smtp.auth", "true");
properties.put("mail.smtp.port", "587");
// Enable STARTTLS
properties.put("mail.smtp.starttls.enable", "true");
properties.put("mail.smtp.starttls.required", "true");
// Accept only TLS 1.1 and 1.2
properties.setProperty("mail.smtp.ssl.enable", "true");
properties.setProperty("mail.smtp.ssl.trust", "192.168.59.99");
properties.setProperty("mail.smtp.ssl.protocols", "TLSv1.2 TLSv1.3");
// properties.put("mail.transport.protocol.rfc822", "smtp");
session = Session.getInstance(properties, new Authenticator() {
@Override
protected PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication("jacques.durand@ca.lan", "us3r");
}
});
if (session == null) {
throw new RuntimeException("Error creating mail session.");
}
session.setDebug(true);
// message
Message message = new MimeMessage(session);
message.setFrom(new InternetAddress("jacques.durand@ca.lan"));
message.setRecipients(Message.RecipientType.TO, InternetAddress.parse("jacques.durand@ca.lan"));
message.setSubject("TestMail");
message.setText("TestMail");
Transport.send(message);
}
}
Unsuccessful java properties :
Properties properties = System.getProperties();
properties.setProperty("mail.smtp.host", "192.168.59.99");
properties.setProperty("mail.smtp.port", "587");
properties.put("mail.smtp.auth", true);
properties.put("mail.smtp.socketFactory.port", "587");
properties.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
properties.put("mail.smtp.socketFactory.fallback", "false");
properties.put("mail.smtp.ssl.enable", "true");
properties.put("mail.smtp.ssl.protocols", "TLSv1.2");
properties.put("mail.smtp.starttls.enable", "true");
properties.put("mail.smtp.starttls.required", "true");
////
properties.put("mail.smtps.host", "192.168.59.99");
properties.put("mail.smtps.port", "587");
properties.put("mail.smtps.socketFactory.port", "587");
properties.put("mail.smtps.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
properties.put("mail.smtps.socketFactory.fallback", "false");
properties.put("mail.transport.protocol", "smtps");
properties.put("mail.smtps.ssl.enable","true");
properties.put("mail.smtps.starttls.enable","false");
properties.put("mail.smtps.auth", "true");
properties.put("mail.smtps.ssl.protocols", "TLSv1.2");
///
properties.put("mail.transport.protocol.rfc822", "smtp");
The librairies I tried :
- javax.mail : 1.5.0-b01
- javax.mail : 1.6.2
- jakarta.mail : 2.0.1
I would like to force the TLSv1.2 or TLSv1.3 protocol on port 587.
