Error in authentication using JavaMailSenderImpl

Question

I built a Spring boot/angular application which has a feedback sending fuctionality, but every time I try to send an email I'm getting this error.I tried almost every solution, but it didn't help me

• Two-factor auth is turned ON
• There are no typo in username or application password
• Waited >10 minutes between tries, to allow for some "cool-off" between unsuccessful authorisations

Stack Trace

2022-09-18 14:51:57.334 ERROR 24544 --- [nio-8080-exec-1] o.a.c.c.C.[.[.[/].[dispatcherServlet]    : Servlet.service() for servlet [dispatcherServlet] in context with path [] threw exception [Request processing failed; nested exception is org.springframework.mail.MailAuthenticationException: Authentication failed; nested exception is javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8  https://support.google.com/mail/?p=BadCredentials v10-20020ac258ea000000b0049f907b9ba9sm397640lfo.226 - gsmtp
] with root cause

javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8  https://support.google.com/mail/?p=BadCredentials v10-20020ac258ea000000b0049f907b9ba9sm397640lfo.226 - gsmtp

    at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:947) ~[jakarta.mail-1.6.7.jar:1.6.7]
    at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:858) ~[jakarta.mail-1.6.7.jar:1.6.7]
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:762) ~[jakarta.mail-1.6.7.jar:1.6.7]
    at javax.mail.Service.connect(Service.java:342) ~[jakarta.mail-1.6.7.jar:1.6.7]
    at org.springframework.mail.javamail.JavaMailSenderImpl.connectTransport(JavaMailSenderImpl.java:518) ~[spring-context-support-5.3.22.jar:5.3.22]
    at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:437) ~[spring-context-support-5.3.22.jar:5.3.22]
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:323) ~[spring-context-support-5.3.22.jar:5.3.22]
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:312) ~[spring-context-support-5.3.22.jar:5.3.22]
    at com.example.notebooktest.mail.FeedbackMailSender.sendFeedback(FeedbackMailSender.java:40) ~[classes/:na]
    at com.example.notebooktest.api.FeedbackController.sendFeedback(FeedbackController.java:30) ~[classes/:na]
    at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[na:na]
    at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62) ~[na:na]
    at java.base/jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[na:na]
    at java.base/java.lang.reflect.Method.invoke(Method.java:566) ~[na:na]
    at org.springframework.web.method.support.InvocableHandlerMethod.doInvoke(InvocableHandlerMethod.java:205) ~[spring-web-5.3.22.jar:5.3.22]
    at org.springframework.web.method.support.InvocableHandlerMethod.invokeForRequest(InvocableHandlerMethod.java:150) ~[spring-web-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.mvc.method.annotation.ServletInvocableHandlerMethod.invokeAndHandle(ServletInvocableHandlerMethod.java:117) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.mvc.method.annotation.RequestMappingHandlerAdapter.invokeHandlerMethod(RequestMappingHandlerAdapter.java:895) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.mvc.method.annotation.RequestMappingHandlerAdapter.handleInternal(RequestMappingHandlerAdapter.java:808) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.mvc.method.AbstractHandlerMethodAdapter.handle(AbstractHandlerMethodAdapter.java:87) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.DispatcherServlet.doDispatch(DispatcherServlet.java:1070) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.DispatcherServlet.doService(DispatcherServlet.java:963) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.FrameworkServlet.processRequest(FrameworkServlet.java:1006) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.FrameworkServlet.doPost(FrameworkServlet.java:909) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at javax.servlet.http.HttpServlet.service(HttpServlet.java:681) ~[tomcat-embed-core-9.0.65.jar:4.0.FR]
    at org.springframework.web.servlet.FrameworkServlet.service(FrameworkServlet.java:883) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at javax.servlet.http.HttpServlet.service(HttpServlet.java:764) ~[tomcat-embed-core-9.0.65.jar:4.0.FR]
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:227) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:162) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:53) ~[tomcat-embed-websocket-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:189) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:162) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.springframework.web.filter.RequestContextFilter.doFilterInternal(RequestContextFilter.java:100) ~[spring-web-5.3.22.jar:5.3.22]
    at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:117) ~[spring-web-5.3.22.jar:5.3.22]
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:189) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:162) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.springframework.web.filter.FormContentFilter.doFilterInternal(FormContentFilter.java:93) ~[spring-web-5.3.22.jar:5.3.22]
    at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:117) ~[spring-web-5.3.22.jar:5.3.22]
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:189) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:162) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.springframework.web.filter.CharacterEncodingFilter.doFilterInternal(CharacterEncodingFilter.java:201) ~[spring-web-5.3.22.jar:5.3.22]
    at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:117) ~[spring-web-5.3.22.jar:5.3.22]
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:189) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:162) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:197) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:97) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:541) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:135) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:92) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:78) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:360) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.coyote.http11.Http11Processor.service(Http11Processor.java:399) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.coyote.AbstractProcessorLight.process(AbstractProcessorLight.java:65) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.coyote.AbstractProtocol$ConnectionHandler.process(AbstractProtocol.java:890) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.doRun(NioEndpoint.java:1789) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.tomcat.util.net.SocketProcessorBase.run(SocketProcessorBase.java:49) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.tomcat.util.threads.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1191) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.tomcat.util.threads.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:659) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:61) ~[tomcat-embed-core-9.0.65.jar:9.0.65]
    at java.base/java.lang.Thread.run(Thread.java:834) ~[na:na]

application.properties

server.port=8080
spring.datasource.driver-class-name=org.postgresql.Driver
spring.datasource.url=jdbc:postgresql://localhost:5432/NotebookTest
spring.datasource.username=postgres
spring.datasource.password=1111
notebookTest.db.create.default=true
spring.jpa.show-sql=true
spring.jpa.hibernate.ddl-auto=update
spring.jpa.properties.hibernate.dialect=org.hibernate.dialect.PostgreSQL95Dialect

spring.mail.host=smtp.gmail.com
spring.mail.port=587
spring.mail.username="************@gmail.com"
spring.mail.password=***************
spring.mail.properties.mail.smtp.starttls.enable=true
spring.mail.properties.mail.smtp.starttls.required=true
spring.mail.properties.mail.smtp.auth=true

FeedbackMailSender.class

package com.example.notebooktest.mail;
import org.springframework.core.env.Environment;
import org.springframework.mail.SimpleMailMessage;
import org.springframework.mail.javamail.JavaMailSenderImpl;
import org.springframework.stereotype.Component;
import java.util.Properties;

@Component
public class FeedbackMailSender implements FeedbackSender {

    private JavaMailSenderImpl mailSender;
    private Properties mailProperties = new Properties();

    public FeedbackMailSender(Environment environment) {
        this.mailSender = new JavaMailSenderImpl();
        this.mailProperties.put("mail.smtp.starttls.enable", true);

        mailSender.setJavaMailProperties(mailProperties);
        mailSender.setHost(environment.getProperty("spring.mail.host"));
        mailSender.setPort(Integer.parseInt(environment.getProperty("spring.mail.port")));
        mailSender.setUsername(environment.getProperty("spring.mail.username"));
        mailSender.setPassword(environment.getProperty("spring.mail.password"));

    }

    @Override
    public void sendFeedback(String from, String name, String feedback) {
        SimpleMailMessage message = new SimpleMailMessage();
        message.setTo("*******@list.ru");
        message.setSubject("New feedback from" + name);
        message.setText(feedback);
        message.setFrom(from);

        mailSender.send(message);
    }

Http Controller

import com.example.notebooktest.api.Dto.FeedbackDto;
import com.example.notebooktest.mail.FeedbackSender;
import org.springframework.validation.BindingResult;
import org.springframework.web.bind.annotation.*;
import javax.xml.bind.ValidationException;

@RestController
@CrossOrigin
@RequestMapping("/api/feedback")
public class FeedbackController {
    private FeedbackSender feedbackSender;

    public FeedbackController(FeedbackSender feedbackSender) {
        this.feedbackSender = feedbackSender;
    }

    @PostMapping
    public void sendFeedback(@RequestBody FeedbackDto feedbackDto, BindingResult bindingResult)
            throws ValidationException {
        if (bindingResult.hasErrors()) {
            throw new ValidationException("Feedback has Errors");
        }

        this.feedbackSender.sendFeedback(
                feedbackDto.getEmail(),
                feedbackDto.getName(),
                feedbackDto.getFeedback());

    }
}

Answer 1

Turned out that you shouldn't type quotation marks, when specifying your email:

spring.mail.username=************@gmail.com

Instead of

spring.mail.username="************@gmail.com"