Java Mail API

Mail Config

import java.util.Properties;

import org.springframework.beans.factory.annotation.Autowired;
import org.springframework.context.annotation.Bean;
import org.springframework.context.annotation.Configuration;
import org.springframework.mail.javamail.JavaMailSender;
import org.springframework.mail.javamail.JavaMailSenderImpl;

@Configuration
public class MailConfig {

    @Bean
    public JavaMailSender getMailSender() {
        JavaMailSenderImpl mailSender = new JavaMailSenderImpl();
        mailSender.setHost("mail.chorke.org");
        mailSender.setPort(465);

        if(!"[email protected]".isEmpty()) {
            mailSender.setUsername("[email protected]");
            mailSender.setPassword("p@$$w0rd");
        }

        Properties javaMailProperties = new Properties();
        javaMailProperties.put("mail.smtp.auth", "[email protected]".isEmpty() ?  "false" : "true");
        javaMailProperties.put("mail.smtp.ehlo", "true");

        javaMailProperties.put("mail.smtp.ssl.trust", "mail.chorke.org");
        javaMailProperties.put("mail.smtp.starttls.enable", "true");
        javaMailProperties.put("mail.smtp.ssl.enable", "true");

        javaMailProperties.put("mail.transport.protocol", "smtp");
        javaMailProperties.put("mail.debug", "true");

        mailSender.setJavaMailProperties(javaMailProperties);
        return mailSender;
    }
}

Knowledge

# debugging certificate handshacking
service='api.chorke.org:5443/soap/services';\
echo -e "GET / HTTP/1.0\r\n" | openssl s_client \
-connect $service -CAfile chorke_client.pem

openssl help
openssl help pkcs12
keytool --help -importkeystore
openssl s_client -connect mail.chorke.org:465 -state

sudo keytool -import -trustcacerts -alias letsencrypt_r3 -file lets-encrypt-r3.der -keystore\
 /usr/lib/jvm/java-8-openjdk-amd64/jre/lib/security/cacerts

sudo keytool -import -trustcacerts -alias letsencrypt_r3 -file lets-encrypt-r3.der -keystore\
 /etc/ssl/certs/java/cacerts

Enter keystore password: changeit

References

Java Mail cannot connect to SMTP using TLS/SSL Let’s Encrypt Chain of Trust Jakarta Mail API Java Key Store Java/Security Java Mail API Java