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Client was not authenticated to send anonymous mail during MAIL FROM

I am trying to send an email in a java application calling this method:
public static void sendEmail() {
// Create object of Property file
Properties props = new Properties();
// this will set host of server- you can change based on your requirement
props.put("mail.smtp.host", "smtp.office365.com");
// set the port of socket factory
//props.put("mail.smtp.socketFactory.port", "587");
// set socket factory
//props.put("mail.smtp.socketFactory.class","javax.net.ssl.SSLSocketFactory");
// set the authentication to true
props.put("mail.smtp.auth", "true");
// set the port of SMTP server
props.put("mail.smtp.port", "587");
// This will handle the complete authentication
Session session = Session.getDefaultInstance(props,
new javax.mail.Authenticator() {
protected PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication("xx#mail.com", "xx");
}
});
try {
// Create object of MimeMessage class
Message message = new MimeMessage(session);
// Set the from address
message.setFrom(new InternetAddress("xx#mail.com"));
// Set the recipient address
message.setRecipients(Message.RecipientType.TO,InternetAddress.parse("yy#mail.com"));
// Add the subject link
message.setSubject("Testing Subject");
// Create object to add multimedia type content
BodyPart messageBodyPart1 = new MimeBodyPart();
// Set the body of email
messageBodyPart1.setText("This is message body");
// Create object of MimeMultipart class
Multipart multipart = new MimeMultipart();
// add body part 2
multipart.addBodyPart(messageBodyPart1);
// set the content
message.setContent(multipart);
// finally send the email
Transport.send(message);
System.out.println("=====Email Sent=====");
} catch (MessagingException e) {
throw new RuntimeException(e);
}
}
but for some reason when the debug hits Transport.send(), I got this exception:
com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [DB6PR0802CA0037.eurprd08.prod.outlook.com]
why is this happening even though I used the Authenticator()?

If you connect via port 587 you initially start a plain connection where you have to start TLS by explicitly sending the STARTTLS-command. You have to tell JavaMail to do that, otherwise it will try to proceed unsecured. The SMTP-server doesn't send any authentication-mechanism-informations unless the TLS-connection is established, so JavaMail is assuming that no authentication is needed and tries to send the mail without.
Add the following entry to the properties:
props.put("mail.smtp.starttls.enable", "true");
WIth that JavaMail should try to switch to TLS before trying to authenticate.
If that fails, you need to enable debugging by setting the property
props.put("mail.debug", "true");
and post the output here.

Postfix returning Invalid Addresses; 454 <to#domain.com>: Relay access denied

I'm using a pre-configured Postfix server and interacting with it using JavaMail. I am trying to send email notifications to any external domain that may request it.
Here is the java method to send a test email:
public void TestEmail() {
String to = "to#domain.com";
String from = "noreply#hostdomain.com";
final String username = "user";
final String password = "password";
String host = "xxx.xxx.xxx.xxx";
Properties props = new Properties();
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.starttls.enable", "true");
props.put("mail.smtp.host", host);
props.put("mail.smtp.port", "587");
Session session = Session.getInstance(props,
new Authenticator() {
protected PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication(username, password);
}
});
try {
Message message = new MimeMessage(session);
message.setFrom(new InternetAddress(from));
message.setRecipients(Message.RecipientType.TO, InternetAddress.parse(to));
message.setSubject("Test Email");
message.setContent("This is a test email", "text/html");
Transport.send(message);
System.out.println("The test message was sent!");
} catch (MessagingException e) {
throw new RuntimeException(e);
}
}
When I run the method that contains the JavaMail code, I get
generalError: javax.mail.SendFailedException: Invalid Addresses;
nested exception is:
com.sun.mail.smtp.SMTPAddressFailedException: 454 4.7.1 <to#domain.com>: Relay access denied
I was able to test outgoing mail from the Postfix server using
echo "This is the body" | mail -s "This is the subject" to#domain.com
and did receive the email in the testing inbox.
I'm not 100% sure what all the settings are on the Postfix server, but I am suspecting that is where the issue is, but I'm not familiar enough with it to start digging around and changing things all willy-nilly.
EDIT:
I removed the Authenticator() set up from the Session creation and replaced Transport.send() with recommended code block
Transport transport = session.getTransport("smtp");
transport.connect(host, 587, username, password);
transport.sendMessage(message, message.getAllRecipients());
transport.close();
The entire new set of code is:
String host = "xxx.xxx.xxx.xxx";
Properties props = new Properties();
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.starttls.enable", "true");
props.put("mail.smtp.host", host);
props.put("mail.smtp.port", "587");
Session session = Session.getInstance(props, null);
try {
Message message = new MimeMessage(session);
message.setFrom(new InternetAddress(from));
message.setRecipients(Message.RecipientType.TO, InternetAddress.parse(to));
message.setSubject("Test Email");
message.setContent("This is a test email", "text/html");
Transport transport = session.getTransport("smtp");
transport.connect(host, 587, username, password);
transport.sendMessage(message, message.getAllRecipients());
transport.close();
System.out.println("The test message was sent!");
} catch (MessagingException e) {
System.out.println("Error: " + e);
e.printStackTrace();
throw new RuntimeException(e);
}
}
This has changed the error message I am receiving to: Unrecognized SSL message, plaintext connection?
Solved
Solution: The Java code was not the issue. The Postfix server was not configured to accept emails originating from a non-local IP/host. The IPs were added to the main.cf in the mynetworks variable.

This article has more information.
First, get rid of the Authenticator as described in the JavaMail FAQ. That will ensure that it's really trying to authenticate to the server. Turn on JavaMail session debugging to make sure it is authenticating.
Note that you can replace
Transport transport = session.getTransport("smtp");
transport.connect(host, 587, username, password);
transport.sendMessage(message, message.getAllRecipients());
transport.close();
with
Transport.send(message, username, password);
You can get rid of the mail.smtp.auth setting, but keep the other properties.
Make sure you're using the most current version of JavaMail.
If it still doesn't work, the article above may provide some clues as to how to change the Postfix configuration.

JavaMail exception : Could not connect to smtp host

I am trying to send an email using gmail in a java application. However I keep getting this error.
Severe: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 465, response: -1
I hope someone can help me check if my code is wrong. I have been staring at it for awhile now and am quite stuck. Thanks!
My mailing code
public void sendEmail(String email){
String to=email;
String from="user#gmail.com";
String host="smtp.gmail.com";
Properties properties = System.getProperties();
properties.put("mail.smtp.host", host);
properties.put("mail.smtp.socketFactory.port", String.valueOf(465));
properties.put("mail.smtp.auth", "true");
properties.put("mail.smtp.port", "465");
properties.put("mail.smtp.starttls.enabled", String.valueOf(true));
properties.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
//Session session = Session.getDefaultInstance(properties);
Session session= Session.getInstance(properties, new javax.mail.Authenticator() {
protected PasswordAuthentication getpPasswordAuthentication(){
return new PasswordAuthentication("user#gmail.com", "password");
}
});
try{
MimeMessage message = new MimeMessage(session);
message.setFrom(new InternetAddress(from));
message.addRecipient(javax.mail.Message.RecipientType.TO, new InternetAddress(to));
//set subject header field
message.setSubject("Password reset");
//set actual message
message.setText("Your password has been reset");
//send message
Transport.send(message);
System.out.println("Email has been sent");
}catch(MessagingException mex){
mex.printStackTrace();
}
}

Why Java MailSender does not Recognize the destination email?

I have a MailSender class that has 2 methods:
private Session createSmtpSession(final String fromEmail, final String fromEmailPassword) {
final Properties props = new Properties();
props.setProperty ("mail.host", "smtp.gmail.com");
props.setProperty("mail.smtp.auth", "true");
props.setProperty("mail.smtp.port", "" + 587);
props.setProperty("mail.smtp.starttls.enable", "true");
props.setProperty ("mail.transport.protocol", "smtp");
return Session.getDefaultInstance(props, new javax.mail.Authenticator() {
protected PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication(fromEmail, fromEmailPassword);
}
});
}
public void sendEmail(String subject, String fromEmail, String fromEmailPassword, String content, String toEmail){
Session mailSession = createSmtpSession(fromEmail, fromEmailPassword);
mailSession.setDebug (true);
try {
Transport transport = mailSession.getTransport ();
MimeMessage message = new MimeMessage (mailSession);
message.setSubject (subject);
message.setFrom (new InternetAddress (fromEmail));
message.setContent (content, "text/html");
message.addRecipient (Message.RecipientType.TO, new InternetAddress (toEmail));
transport.connect ();
transport.sendMessage (message, message.getRecipients (Message.RecipientType.TO));
}
catch (MessagingException e) {
System.err.println("Cannot Send email");
e.printStackTrace();
}
}
ok, The way the above code works is like this:
I have personal gmail myEmail#gmail.com & if I want to send msg to destination email like aa#xyz.com from myEmail#gmail.com, then I need to call sendEmail(subject, "myEmail#gmail.com", fromEmailPassword, content, "aa#xyz.com");
But recently I bought VPS from Godaddy & I am using Godaddy Email (info#mydomain.com) so I want to send smg to destination email like aa#xyz.com from info#mydomain.com, then I need to call sendEmail(subject, "info#mydomain.com", fromEmailPassword, content, "aa#xyz.com");
However I got error cos Godaddy using port 25
So I changed the code in createSmtpSession as following:
props.setProperty ("mail.host", "smtp.mydomain.com");
props.setProperty("mail.smtp.port", "" + 25);
However, this time I got other problem
DEBUG SMTP: Sending failed because of invalid destination addresses
RSET
250 2.0.0 OK
DEBUG SMTP: MessagingException while sending, THROW:
javax.mail.SendFailedException: Invalid Addresses;
nested exception is:
com.sun.mail.smtp.SMTPAddressFailedException: 550 5.1.1 <aa#xyz.com> Recipient not found. <http://x.co/irbounce>
Clearly the aa#xyz.com is actually existed, but why the error saying Recipient not found.
SO How to fix this issue?

I need to look at the outgoing (SMTP) server (like smtpout.secureserver.net) in Godaddy Email & now it working fine
props.setProperty ("mail.transport.protocol", "smtps");
props.setProperty ("mail.smtps.host", "smtpout.secureserver.net");
props.setProperty("mail.smtps.auth", "true");
props.setProperty("mail.smtps.port", "" + 465);

Javamail rate for the client exceeded

I need to send at least 200 messages from a stretch. When the program starts, send mail successfully to 15 or 17, then I get this error:
MESSAGE ERROR:
com.sun.mail.smtp.SMTPSendFailedException: 421 4.4.2 Message submission rate for this client has exceeded the configured limit
What I can do?
CODE JAVA
public void mandarEmail(String correos, String mensaje, String asunto) {
Message message;
Properties props = new Properties();
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.starttls.enable", "true");
props.put("mail.transport.protocol", "smtp");
props.setProperty("mail.smtp.port", "587");
props.put("mail.smtp.host", "pod51004.outlook.com");
props.put("mail.smtp.debug", "true");
Session session = Session.getInstance(props, new javax.mail.Authenticator() {
#Override
protected PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication("docemail#usmp.pe", "docpass");
}
});
try {
message = new MimeMessage(session);
message.setFrom(new InternetAddress("USMP - FN <documentos-fn#usmp.pe>"));
message.setSubject(asunto);
message.addRecipients(Message.RecipientType.TO, InternetAddress.parse(correos));
message.addRecipients(Message.RecipientType.BCC, new InternetAddress[]{new InternetAddress("ivan_pro_nice#hotmail.com")});
message.setContent(mensaje, "text/html; charset=utf-8");
Transport transport = session.getTransport("smtp");
transport.connect("docemail#usmp.pe", "docpass");
transport.sendMessage(message, message.getAllRecipients());
transport.close();
} catch (MessagingException e) {
throw new RuntimeException(e);
} finally {
props = null;
message = null;
}
}

That's the server you're connecting to, and not a client issue. Here's a doc on how to parse SMTP codes from the server.
A mail server will reply to every request a client (such as your email
program) makes with a return code. This code consists of three
numbers.
In your case, you're getting 421.

You probably need to pay for a "business" account from your mail server vendor so they'll let you send more email.

if you want to send single email to 200 clients. Than u can add an array of reciever's email addresses of size upto 50.
but i you want to send different msg for each email. Then you can create a new connection to email server with a counter that counts send emails as well as it counts 15 it should create a new connection.
to test your code use mailtrap.io