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Why JavaMailSender - starttls does not work

Time：12-13

I'm trying to configure mail service in simple spring boot app to send email notifications.

Here is my config:

spring:
  main:
    web-application-type: none

  mail:
    host: ${FOOD_MAIL_HOST:smtp.gmail.com}
    port: ${FOOD_MAIL_PORT:587}
    username: ${FOOD_MAIL_USERNAME:[email protected]}
    password: ${FOOD_MAIL_PASSWORD:mypassword}
    properties:
      smtp:
        auth: true
        starttls:
          enable: true
  freemarker:
    charset: UTF-8
    template-loader-path: classpath:/templates

Here is my pom.xml:

<?xml version="1.0" encoding="UTF-8"?>
<project xmlns="http://maven.apache.org/POM/4.0.0"
         xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
         xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 http://maven.apache.org/xsd/maven-4.0.0.xsd">

    <parent>
        <groupId>my.parent.app</groupId>
        <artifactId>my-notification-app</artifactId>
        <version>1.0-SNAPSHOT</version>
    </parent>

    <modelVersion>4.0.0</modelVersion>
    <artifactId>notification-worker</artifactId>

    <properties>
        <maven.compiler.source>11</maven.compiler.source>
        <maven.compiler.target>11</maven.compiler.target>
        <os-maven-plugin.version>1.6.1</os-maven-plugin.version>
        <protobuf-maven-plugin.version>0.6.1</protobuf-maven-plugin.version>
        <grpc-spring-boot-starter.version>4.5.4</grpc-spring-boot-starter.version>
        <jackson-databind.version>2.13.0</jackson-databind.version>
    </properties>

    <dependencies>

        <dependency>
            <groupId>io.github.lognet</groupId>
            <artifactId>grpc-spring-boot-starter</artifactId>
            <version>${grpc-spring-boot-starter.version}</version>
        </dependency>

        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter</artifactId>
            <version>2.6.0</version>
        </dependency>

        <dependency>
            <groupId>org.springframework.kafka</groupId>
            <artifactId>spring-kafka</artifactId>
        </dependency>

        <dependency>
            <groupId>my.service</groupId>
            <artifactId>notification-common</artifactId>
            <version>${project.version}</version>
        </dependency>

        <!-- https://mvnrepository.com/artifact/com.fasterxml.jackson.core/jackson-databind -->
        <dependency>
            <groupId>com.fasterxml.jackson.core</groupId>
            <artifactId>jackson-databind</artifactId>
            <version>${jackson-databind.version}</version>
        </dependency>

        <!-- https://mvnrepository.com/artifact/org.projectlombok/lombok -->
        <dependency>
            <groupId>org.projectlombok</groupId>
            <artifactId>lombok</artifactId>
            <version>${lombok.version}</version>
            <scope>provided</scope>
        </dependency>

        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-mail</artifactId>
        </dependency>

        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-freemarker</artifactId>
        </dependency>

        <dependency>
            <groupId>org.springframework</groupId>
            <artifactId>spring-webmvc</artifactId>
            <version>5.3.9</version>
        </dependency>

        <dependency>
            <groupId>javax.servlet</groupId>
            <artifactId>javax.servlet-api</artifactId>
            <version>3.0.1</version>
            <scope>provided</scope>
        </dependency>

        <!-- Spring-Test-Support (Optional) -->
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-test</artifactId>
            <scope>test</scope>
            <!-- Exclude the test engine you don't need -->
            <exclusions>
                <exclusion>
                    <groupId>org.junit.vintage</groupId>
                    <artifactId>junit-vintage-engine</artifactId>
                </exclusion>
            </exclusions>
        </dependency>

    </dependencies>

    <build>
        <extensions>
            <extension>
                <groupId>kr.motd.maven</groupId>
                <artifactId>os-maven-plugin</artifactId>
                <version>${os-maven-plugin.version}</version>
            </extension>
        </extensions>
        <plugins>
            <plugin>
                <groupId>org.xolstice.maven.plugins</groupId>
                <artifactId>protobuf-maven-plugin</artifactId>
                <version>${protobuf-maven-plugin.version}</version>
                <configuration>
                    <protoSourceRoot>../notification-common/src/main/proto/user</protoSourceRoot>
                    <protocArtifact>
                        com.google.protobuf:protoc:3.3.0:exe:${os.detected.classifier}
                    </protocArtifact>
                    <pluginId>grpc-java</pluginId>
                    <pluginArtifact>
                        io.grpc:protoc-gen-grpc-java:1.4.0:exe:${os.detected.classifier}
                    </pluginArtifact>
                </configuration>
                <executions>
                    <execution>
                        <goals>
                            <goal>compile</goal>
                            <goal>compile-custom</goal>
                        </goals>
                    </execution>
                </executions>
            </plugin>
            <plugin>
                <groupId>org.springframework.boot</groupId>
                <artifactId>spring-boot-maven-plugin</artifactId>
                <executions>
                    <execution>
                        <goals>
                            <goal>repackage</goal>
                        </goals>
                        <configuration>
                            <mainClass>
                                notification.worker.Application
                            </mainClass>
                        </configuration>
                    </execution>
                </executions>
            </plugin>
        </plugins>
    </build>
</project>

hete is my code:

import freemarker.template.Template;
import freemarker.template.TemplateException;
import lombok.RequiredArgsConstructor;
import org.springframework.mail.javamail.JavaMailSender;
import org.springframework.mail.javamail.MimeMessageHelper;
import org.springframework.messaging.MessagingException;
import org.springframework.stereotype.Service;
import org.springframework.ui.freemarker.FreeMarkerTemplateUtils;
import org.springframework.web.servlet.view.freemarker.FreeMarkerConfigurer;

import javax.mail.internet.MimeMessage;
import java.io.IOException;
import java.util.Map;

@Service
@RequiredArgsConstructor
public class EmailService {

    private final FreeMarkerConfigurer freemarkerConfigurer;

    private final JavaMailSender emailSender;

    public void sendMessageUsingFreemarkerTemplate(
            String to, String subject, Map<String, Object> templateModel)
            throws IOException, TemplateException, MessagingException, javax.mail.MessagingException {

        Template freemarkerTemplate = freemarkerConfigurer.getConfiguration()
                .getTemplate("template-freemarker.ftl");
        String htmlBody = FreeMarkerTemplateUtils.processTemplateIntoString(freemarkerTemplate, templateModel);

        sendHtmlMessage(to, subject, htmlBody);
    }

    private void sendHtmlMessage(String to, String subject, String htmlBody) throws MessagingException, javax.mail.MessagingException {
        MimeMessage message = emailSender.createMimeMessage();
//        message
        MimeMessageHelper helper = new MimeMessageHelper(message, true, "UTF-8");
        helper.setTo(to);
        helper.setSubject(subject);
        helper.setText(htmlBody, true);
        emailSender.send(message);
    }
}

here is my test:


import freemarker.template.TemplateException;
import org.junit.jupiter.api.Test;
import org.springframework.beans.factory.annotation.Autowired;
import org.springframework.boot.test.context.SpringBootTest;

import javax.mail.*;
import javax.mail.internet.InternetAddress;
import javax.mail.internet.MimeMessage;
import java.io.IOException;
import java.util.HashMap;
import java.util.Map;
import java.util.Properties;

import static org.junit.jupiter.api.Assertions.*;
import static user.NotificationSettings.NotificationType.ORDER_CREATED;

@SpringBootTest
class EmailServiceTest {

    @Autowired
    private EmailService emailService;

    @Test
    public void testSendEmail() throws TemplateException, IOException, MessagingException {

//        final String username = "[email protected]";
//        final String password = "mypassword";
//
//        final Properties prop = new Properties();
//        prop.put("mail.smtp.host", "smtp.gmail.com");
//        prop.put("mail.smtp.port", "587");
//        prop.put("mail.smtp.auth", "true");
//        prop.put("mail.smtp.starttls.enable", "true"); //TLS
//
//        final Session session = Session.getInstance(prop,
//                new javax.mail.Authenticator() {
//                    protected PasswordAuthentication getPasswordAuthentication() {
//                        return new PasswordAuthentication(username, password);
//                    }
//                });
//
//        try {
//
//            final Message message = new MimeMessage(session);
//            message.setFrom(new InternetAddress("[email protected]"));
//            message.setRecipients(
//                    Message.RecipientType.TO,
//                    InternetAddress.parse("[email protected]")
//            );
//            message.setSubject("Testing Gmail TLS");
//            message.setText("Dear Mail Crawler,"
//                      "\n\n Please do not spam my email!");
//
//            Transport.send(message);
//
//            System.out.println("Done");
//
//        } catch (MessagingException e) {
//            e.printStackTrace();
//        }

        final Map<String, Object> templateModel = new HashMap<>();
        templateModel.put("recipientName", "Mr. Recipient");
        templateModel.put("text", ORDER_CREATED);
        templateModel.put("senderName", "Vanusha");
        emailService.sendMessageUsingFreemarkerTemplate("[email protected]", "test", templateModel);
    }
}

Commented code with similar settings sends mail well. But when i am trying to use JavaMailSender i receive exception:

com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. z1sm5676367edq.54 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2374)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1808)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1285)
    at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:465)
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:361)
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:356)
    at notification.worker.service.EmailService.sendHtmlMessage(EmailService.java:43)
    at notification.worker.service.EmailService.sendMessageUsingFreemarkerTemplate(EmailService.java:33)
    at notification.worker.service.EmailServiceTest.testSendEmail(EmailServiceTest.java:68)
    at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
    at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62)
    at java.base/jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
    at java.base/java.lang.reflect.Method.invoke(Method.java:566)
    at org.junit.platform.commons.util.ReflectionUtils.invokeMethod(ReflectionUtils.java:725)
    at org.junit.jupiter.engine.execution.MethodInvocation.proceed(MethodInvocation.java:60)
    at org.junit.jupiter.engine.execution.InvocationInterceptorChain$ValidatingInvocation.proceed(InvocationInterceptorChain.java:131)
    at org.junit.jupiter.engine.extension.TimeoutExtension.intercept(TimeoutExtension.java:149)
    at org.junit.jupiter.engine.extension.TimeoutExtension.interceptTestableMethod(TimeoutExtension.java:140)
    at org.junit.jupiter.engine.extension.TimeoutExtension.interceptTestMethod(TimeoutExtension.java:84)
    at org.junit.jupiter.engine.execution.ExecutableInvoker$ReflectiveInterceptorCall.lambda$ofVoidMethod$0(ExecutableInvoker.java:115)
    at org.junit.jupiter.engine.execution.ExecutableInvoker.lambda$invoke$0(ExecutableInvoker.java:105)
    at org.junit.jupiter.engine.execution.InvocationInterceptorChain$InterceptedInvocation.proceed(InvocationInterceptorChain.java:106)
    at org.junit.jupiter.engine.execution.InvocationInterceptorChain.proceed(InvocationInterceptorChain.java:64)
    at org.junit.jupiter.engine.execution.InvocationInterceptorChain.chainAndInvoke(InvocationInterceptorChain.java:45)
    at org.junit.jupiter.engine.execution.InvocationInterceptorChain.invoke(InvocationInterceptorChain.java:37)
    at org.junit.jupiter.engine.execution.ExecutableInvoker.invoke(ExecutableInvoker.java:104)
    at org.junit.jupiter.engine.execution.ExecutableInvoker.invoke(ExecutableInvoker.java:98)
    at org.junit.jupiter.engine.descriptor.TestMethodTestDescriptor.lambda$invokeTestMethod$7(TestMethodTestDescriptor.java:214)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.jupiter.engine.descriptor.TestMethodTestDescriptor.invokeTestMethod(TestMethodTestDescriptor.java:210)
    at org.junit.jupiter.engine.descriptor.TestMethodTestDescriptor.execute(TestMethodTestDescriptor.java:135)
    at org.junit.jupiter.engine.descriptor.TestMethodTestDescriptor.execute(TestMethodTestDescriptor.java:66)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$6(NodeTestTask.java:151)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$8(NodeTestTask.java:141)
    at org.junit.platform.engine.support.hierarchical.Node.around(Node.java:137)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$9(NodeTestTask.java:139)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.executeRecursively(NodeTestTask.java:138)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.execute(NodeTestTask.java:95)
    at java.base/java.util.ArrayList.forEach(ArrayList.java:1541)
    at org.junit.platform.engine.support.hierarchical.SameThreadHierarchicalTestExecutorService.invokeAll(SameThreadHierarchicalTestExecutorService.java:41)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$6(NodeTestTask.java:155)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$8(NodeTestTask.java:141)
    at org.junit.platform.engine.support.hierarchical.Node.around(Node.java:137)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$9(NodeTestTask.java:139)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.executeRecursively(NodeTestTask.java:138)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.execute(NodeTestTask.java:95)
    at java.base/java.util.ArrayList.forEach(ArrayList.java:1541)
    at org.junit.platform.engine.support.hierarchical.SameThreadHierarchicalTestExecutorService.invokeAll(SameThreadHierarchicalTestExecutorService.java:41)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$6(NodeTestTask.java:155)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$8(NodeTestTask.java:141)
    at org.junit.platform.engine.support.hierarchical.Node.around(Node.java:137)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.lambda$executeRecursively$9(NodeTestTask.java:139)
    at org.junit.platform.engine.support.hierarchical.ThrowableCollector.execute(ThrowableCollector.java:73)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.executeRecursively(NodeTestTask.java:138)
    at org.junit.platform.engine.support.hierarchical.NodeTestTask.execute(NodeTestTask.java:95)
    at org.junit.platform.engine.support.hierarchical.SameThreadHierarchicalTestExecutorService.submit(SameThreadHierarchicalTestExecutorService.java:35)
    at org.junit.platform.engine.support.hierarchical.HierarchicalTestExecutor.execute(HierarchicalTestExecutor.java:57)
    at org.junit.platform.engine.support.hierarchical.HierarchicalTestEngine.execute(HierarchicalTestEngine.java:54)
    at org.junit.platform.launcher.core.EngineExecutionOrchestrator.execute(EngineExecutionOrchestrator.java:107)
    at org.junit.platform.launcher.core.EngineExecutionOrchestrator.execute(EngineExecutionOrchestrator.java:88)
    at org.junit.platform.launcher.core.EngineExecutionOrchestrator.lambda$execute$0(EngineExecutionOrchestrator.java:54)
    at org.junit.platform.launcher.core.EngineExecutionOrchestrator.withInterceptedStreams(EngineExecutionOrchestrator.java:67)
    at org.junit.platform.launcher.core.EngineExecutionOrchestrator.execute(EngineExecutionOrchestrator.java:52)
    at org.junit.platform.launcher.core.DefaultLauncher.execute(DefaultLauncher.java:114)
    at org.junit.platform.launcher.core.DefaultLauncher.execute(DefaultLauncher.java:86)
    at org.junit.platform.launcher.core.DefaultLauncherSession$DelegatingLauncher.execute(DefaultLauncherSession.java:86)
    at org.junit.platform.launcher.core.SessionPerRequestLauncher.execute(SessionPerRequestLauncher.java:53)
    at com.intellij.junit5.JUnit5IdeaTestRunner.startRunnerWithArgs(JUnit5IdeaTestRunner.java:69)
    at com.intellij.rt.junit.IdeaTestRunner$Repeater.startRunnerWithArgs(IdeaTestRunner.java:33)
    at com.intellij.rt.junit.JUnitStarter.prepareStreamsAndStart(JUnitStarter.java:230)
    at com.intellij.rt.junit.JUnitStarter.main(JUnitStarter.java:58)

I cannnot figure out the problem all tutorials explain that following part is the key:

     smtp:
        auth: true
        starttls:
          enable: true

But my service is not working. Please help.

CodePudding user response：

I guess your config is not correct. Instead of

  mail:
    properties:
      smtp:
        auth: true
        starttls:
          enable: true

You should try :

  mail:
    properties:
      mail:
        smtp:
          auth: true
          starttls:
            enable: true

Correlating it with properties where we usually define it like following:

spring.mail.properties.mail.smtp.auth=true
spring.mail.properties.mail.smtp.starttls.enable=true

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