Using JavaMail with TLS

Question

I found several other questions on SO regarding the JavaMail API and sending mail through an SMTP server  but none of them discussed using TLS security  I m trying to use JavaMail to send status updates to myself through my work SMTP mail server  but it requires TLS  and I can t find any examples online of how to use JavaMail to access an SMTP server that requires TLS encryption  Can anyone help with this

User · Answer

Good post  the line   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory      is mandatory if the SMTP server uses SSL Authentication  like the GMail SMTP server does  However if the server uses Plaintext Authentication over TLS  it should not be present  because Java Mail will complain about the initial connection being plaintext   Also make sure you are using the latest version of Java Mail  Recently I used some old Java Mail jars from a previous project and could not make the code work  because the login process was failing  After I have upgraded to the latest version of Java Mail  the reason of the error became clear  it was a javax net ssl SSLHandshakeException  which was not thrown up in the old version of the lib

User · Answer

We actually have some notification code in our product that uses TLS to send mail if it is available   You will need to set the Java Mail properties  You only need the TLS one but you might need SSL if your SMTP server uses SSL   Properties props   new Properties    props put  mail smtp starttls enable   true    props put  mail smtp auth    true        If you need to authenticate    Use the following if you need SSL props put  mail smtp socketFactory port   d port   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory    props put  mail smtp socketFactory fallback    false      You can then either pass this to a JavaMail Session or any other session instantiator like Session getDefaultInstance props

User · Answer

As a small note  it only started to work for me when I changed smtp to smtps in the examples above per samples from javamail  see smtpsend java  https   github com javaee javamail releases download JAVAMAIL-1 6 2 javamail-samples zip  option -S   My resulting code is as follow  Properties props new Properties    props put  quot mail smtps starttls enable quot   quot true quot       Use the following if you need SSL props put  quot mail smtps socketFactory port quot   port   props put  quot mail smtps socketFactory class quot    quot javax net ssl SSLSocketFactory quot    props put  quot mail smtps socketFactory fallback quot    quot false quot    props put  quot mail smtps host quot   serverList get randNum    Session session   Session getDefaultInstance props    smtpConnectionPool   new SmtpConnectionPool      SmtpConnectionFactories newSmtpFactory session         final ClosableSmtpConnection transport   smtpConnectionPool borrowObject        transport sendMessage message  message getAllRecipients

User · Answer

Good post  the line   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory      is mandatory if the SMTP server uses SSL Authentication  like the GMail SMTP server does  However if the server uses Plaintext Authentication over TLS  it should not be present  because Java Mail will complain about the initial connection being plaintext   Also make sure you are using the latest version of Java Mail  Recently I used some old Java Mail jars from a previous project and could not make the code work  because the login process was failing  After I have upgraded to the latest version of Java Mail  the reason of the error became clear  it was a javax net ssl SSLHandshakeException  which was not thrown up in the old version of the lib

User · Answer

Just use the following code   It is really useful to send email via Java  and it works    import java util    import javax activation CommandMap  import javax activation MailcapCommandMap  import javax mail    import javax mail Provider  import javax mail internet     public class Main        public static void main String   args                final String username  your gmail com               final String password  password               Properties prop new Properties                prop put  mail smtp auth    true                prop put  mail smtp host    smtp gmail com                prop put  mail smtp port    587                prop put  mail smtp starttls enable    true                 Session session   Session getDefaultInstance prop            new javax mail Authenticator                 protected PasswordAuthentication getPasswordAuthentication                     return new PasswordAuthentication username  password                                     try                    String body  Dear Renish Khunt Welcome                    String htmlBody     lt strong gt This is an HTML Message lt  strong gt                     String textBody    This is a Text Message             Message message   new MimeMessage session            message setFrom new InternetAddress  your gmail com                      message setRecipients Message RecipientType TO InternetAddress parse  receiver gmail com             message setSubject  Testing Subject            MailcapCommandMap mc    MailcapCommandMap  CommandMap getDefaultCommandMap            mc addMailcap  text html   x-java-content-handler com sun mail handlers text html            mc addMailcap  text xml   x-java-content-handler com sun mail handlers text xml            mc addMailcap  text plain   x-java-content-handler com sun mail handlers text plain            mc addMailcap  multipart     x-java-content-handler com sun mail handlers multipart mixed            mc addMailcap  message rfc822   x-java-content-handler com sun mail handlers message rfc822            CommandMap setDefaultCommandMap mc               message setText htmlBody                           message setContent textBody   text html                Transport send message                System out println  Done               catch  MessagingException e                e printStackTrace

User · Answer

With Simple Java Mail 5 0 0  simplejavamail org  it is very straightforward and the library will take care of all the Session properties for you   Here s an example using Google s SMTP servers   Email email   EmailBuilder startingBlank            from  lollypop    lol pop somemail com            to  C Cane    candycane candyshop org            withSubject  hey            withPlainText  We should meet up             withHTMLText   lt b gt We should meet up  lt  b gt             buildEmail     MailerBuilder withSMTPServer  smtp gmail com   25   user    pass   SMTP TLS           buildMailer            sendMail email    MailerBuilder withSMTPServer  smtp gmail com   587   user    pass   SMTP TLS           buildMailer            sendMail email    MailerBuilder withSMTPServer  smtp gmail com   465   user    pass   SMTP SSL           buildMailer            sendMail email     If you have two-factor login turned on  you need to generate an application specific password from your Google account

User · Answer

Good post  the line   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory      is mandatory if the SMTP server uses SSL Authentication  like the GMail SMTP server does  However if the server uses Plaintext Authentication over TLS  it should not be present  because Java Mail will complain about the initial connection being plaintext   Also make sure you are using the latest version of Java Mail  Recently I used some old Java Mail jars from a previous project and could not make the code work  because the login process was failing  After I have upgraded to the latest version of Java Mail  the reason of the error became clear  it was a javax net ssl SSLHandshakeException  which was not thrown up in the old version of the lib

User · Answer

The settings from the example above didn t work for the server I was using  authsmtp com    I kept on getting this error   javax net ssl SSLException  Unrecognized SSL message  plaintext connection    I removed the mail smtp socketFactory settings and everything worked   The final settings were this  SMTP auth was not used and I set the port elsewhere    java util Properties props   new java util Properties    props put  mail smtp starttls enable    true

User · Answer

Good post  the line   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory      is mandatory if the SMTP server uses SSL Authentication  like the GMail SMTP server does  However if the server uses Plaintext Authentication over TLS  it should not be present  because Java Mail will complain about the initial connection being plaintext   Also make sure you are using the latest version of Java Mail  Recently I used some old Java Mail jars from a previous project and could not make the code work  because the login process was failing  After I have upgraded to the latest version of Java Mail  the reason of the error became clear  it was a javax net ssl SSLHandshakeException  which was not thrown up in the old version of the lib

User · Answer

As a small note  it only started to work for me when I changed smtp to smtps in the examples above per samples from javamail  see smtpsend java  https   github com javaee javamail releases download JAVAMAIL-1 6 2 javamail-samples zip  option -S   My resulting code is as follow  Properties props new Properties    props put  quot mail smtps starttls enable quot   quot true quot       Use the following if you need SSL props put  quot mail smtps socketFactory port quot   port   props put  quot mail smtps socketFactory class quot    quot javax net ssl SSLSocketFactory quot    props put  quot mail smtps socketFactory fallback quot    quot false quot    props put  quot mail smtps host quot   serverList get randNum    Session session   Session getDefaultInstance props    smtpConnectionPool   new SmtpConnectionPool      SmtpConnectionFactories newSmtpFactory session         final ClosableSmtpConnection transport   smtpConnectionPool borrowObject        transport sendMessage message  message getAllRecipients

User · Answer

We actually have some notification code in our product that uses TLS to send mail if it is available   You will need to set the Java Mail properties  You only need the TLS one but you might need SSL if your SMTP server uses SSL   Properties props   new Properties    props put  mail smtp starttls enable   true    props put  mail smtp auth    true        If you need to authenticate    Use the following if you need SSL props put  mail smtp socketFactory port   d port   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory    props put  mail smtp socketFactory fallback    false      You can then either pass this to a JavaMail Session or any other session instantiator like Session getDefaultInstance props

User · Answer

The settings from the example above didn t work for the server I was using  authsmtp com    I kept on getting this error   javax net ssl SSLException  Unrecognized SSL message  plaintext connection    I removed the mail smtp socketFactory settings and everything worked   The final settings were this  SMTP auth was not used and I set the port elsewhere    java util Properties props   new java util Properties    props put  mail smtp starttls enable    true

User · Answer

We actually have some notification code in our product that uses TLS to send mail if it is available   You will need to set the Java Mail properties  You only need the TLS one but you might need SSL if your SMTP server uses SSL   Properties props   new Properties    props put  mail smtp starttls enable   true    props put  mail smtp auth    true        If you need to authenticate    Use the following if you need SSL props put  mail smtp socketFactory port   d port   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory    props put  mail smtp socketFactory fallback    false      You can then either pass this to a JavaMail Session or any other session instantiator like Session getDefaultInstance props

User · Answer

With Simple Java Mail 5 0 0  simplejavamail org  it is very straightforward and the library will take care of all the Session properties for you   Here s an example using Google s SMTP servers   Email email   EmailBuilder startingBlank            from  lollypop    lol pop somemail com            to  C Cane    candycane candyshop org            withSubject  hey            withPlainText  We should meet up             withHTMLText   lt b gt We should meet up  lt  b gt             buildEmail     MailerBuilder withSMTPServer  smtp gmail com   25   user    pass   SMTP TLS           buildMailer            sendMail email    MailerBuilder withSMTPServer  smtp gmail com   587   user    pass   SMTP TLS           buildMailer            sendMail email    MailerBuilder withSMTPServer  smtp gmail com   465   user    pass   SMTP SSL           buildMailer            sendMail email     If you have two-factor login turned on  you need to generate an application specific password from your Google account

User · Answer

Just use the following code   It is really useful to send email via Java  and it works    import java util    import javax activation CommandMap  import javax activation MailcapCommandMap  import javax mail    import javax mail Provider  import javax mail internet     public class Main        public static void main String   args                final String username  your gmail com               final String password  password               Properties prop new Properties                prop put  mail smtp auth    true                prop put  mail smtp host    smtp gmail com                prop put  mail smtp port    587                prop put  mail smtp starttls enable    true                 Session session   Session getDefaultInstance prop            new javax mail Authenticator                 protected PasswordAuthentication getPasswordAuthentication                     return new PasswordAuthentication username  password                                     try                    String body  Dear Renish Khunt Welcome                    String htmlBody     lt strong gt This is an HTML Message lt  strong gt                     String textBody    This is a Text Message             Message message   new MimeMessage session            message setFrom new InternetAddress  your gmail com                      message setRecipients Message RecipientType TO InternetAddress parse  receiver gmail com             message setSubject  Testing Subject            MailcapCommandMap mc    MailcapCommandMap  CommandMap getDefaultCommandMap            mc addMailcap  text html   x-java-content-handler com sun mail handlers text html            mc addMailcap  text xml   x-java-content-handler com sun mail handlers text xml            mc addMailcap  text plain   x-java-content-handler com sun mail handlers text plain            mc addMailcap  multipart     x-java-content-handler com sun mail handlers multipart mixed            mc addMailcap  message rfc822   x-java-content-handler com sun mail handlers message rfc822            CommandMap setDefaultCommandMap mc               message setText htmlBody                           message setContent textBody   text html                Transport send message                System out println  Done               catch  MessagingException e                e printStackTrace

User · Answer

We actually have some notification code in our product that uses TLS to send mail if it is available   You will need to set the Java Mail properties  You only need the TLS one but you might need SSL if your SMTP server uses SSL   Properties props   new Properties    props put  mail smtp starttls enable   true    props put  mail smtp auth    true        If you need to authenticate    Use the following if you need SSL props put  mail smtp socketFactory port   d port   props put  mail smtp socketFactory class    javax net ssl SSLSocketFactory    props put  mail smtp socketFactory fallback    false      You can then either pass this to a JavaMail Session or any other session instantiator like Session getDefaultInstance props

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