Google Mail not working for SMTP

[tobsowo]

Kindly assist with sending emails using Google SMTP

I have the email account created in Google Workspace
Create an Password App Password and use the following credentials:
SMTP hostname: smtp.gmail.com
SMTP port: 587
SMTP Protocol (smtp or smtps): smtp
SMTP Username: [email protected]
SMTP Password: Redacted

I get this error in log
[WARN ] 2023-08-02 16:10:58.813 [scheduling-1] NotificationManager - could not send message:
org.springframework.mail.MailSendException: Failed messages: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. h11-20020a2e9ecb000000b002b9e6d7f72fsm1910520ljk.5 - gsmtp

    at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:491) ~[spring-context-support-5.3.18.jar!/:5.3.18]
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:361) ~[spring-context-support-5.3.18.jar!/:5.3.18]
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:378) ~[spring-context-support-5.3.18.jar!/:5.3.18]
    at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:366) ~[spring-context-support-5.3.18.jar!/:5.3.18]
    at alfio.manager.system.SmtpMailer.send(SmtpMailer.java:95) ~[classes!/:?]
    at alfio.manager.system.DefaultMailer.send(DefaultMailer.java:64) ~[classes!/:?]
    at alfio.manager.NotificationManager.sendMessage(NotificationManager.java:413) ~[classes!/:?]
    at alfio.manager.NotificationManager.lambda$processMessage$18(NotificationManager.java:398) ~[classes!/:?]
    at org.springframework.transaction.support.TransactionTemplate.execute(TransactionTemplate.java:140) ~[spring-tx-5.3.18.jar!/:5.3.18]
    at alfio.manager.NotificationManager.processMessage(NotificationManager.java:397) ~[classes!/:?]
    at alfio.manager.NotificationManager.lambda$sendWaitingMessages$14(NotificationManager.java:381) ~[classes!/:?]
    at java.util.stream.ReferencePipeline$4$1.accept(ReferencePipeline.java:214) [?:?]
    at java.util.ArrayList$ArrayListSpliterator.forEachRemaining(ArrayList.java:1625) [?:?]
    at java.util.stream.AbstractPipeline.copyInto(AbstractPipeline.java:509) [?:?]
    at java.util.stream.AbstractPipeline.wrapAndCopyInto(AbstractPipeline.java:499) [?:?]
    at java.util.stream.ForEachOps$ForEachOp.evaluateSequential(ForEachOps.java:150) [?:?]
    at java.util.stream.ForEachOps$ForEachOp$OfInt.evaluateSequential(ForEachOps.java:188) [?:?]
    at java.util.stream.AbstractPipeline.evaluate(AbstractPipeline.java:234) [?:?]
    at java.util.stream.IntPipeline.forEach(IntPipeline.java:463) [?:?]
    at java.util.stream.ReferencePipeline$8$1.accept(ReferencePipeline.java:324) [?:?]
    at java.util.HashMap$EntrySpliterator.forEachRemaining(HashMap.java:1850) [?:?]
    at java.util.stream.AbstractPipeline.copyInto(AbstractPipeline.java:509) [?:?]
    at java.util.stream.AbstractPipeline.wrapAndCopyInto(AbstractPipeline.java:499) [?:?]
    at java.util.stream.ReduceOps$ReduceOp.evaluateSequential(ReduceOps.java:921) [?:?]
    at java.util.stream.AbstractPipeline.evaluate(AbstractPipeline.java:234) [?:?]
    at java.util.stream.IntPipeline.reduce(IntPipeline.java:515) [?:?]
    at java.util.stream.IntPipeline.sum(IntPipeline.java:473) [?:?]
    at alfio.manager.NotificationManager.sendWaitingMessages(NotificationManager.java:382) [classes!/:?]
    at alfio.manager.NotificationManager$$FastClassBySpringCGLIB$$3482d7f4.invoke(<generated>) [classes!/:?]
    at org.springframework.cglib.proxy.MethodProxy.invoke(MethodProxy.java:218) [spring-core-5.3.18.jar!/:5.3.18]
    at org.springframework.aop.framework.CglibAopProxy$CglibMethodInvocation.invokeJoinpoint(CglibAopProxy.java:783) [spring-aop-5.3.18.jar!/:5.3.18]
    at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:163) [spring-aop-5.3.18.jar!/:5.3.18]
    at org.springframework.aop.framework.CglibAopProxy$CglibMethodInvocation.proceed(CglibAopProxy.java:753) [spring-aop-5.3.18.jar!/:5.3.18]
    at org.springframework.transaction.interceptor.TransactionInterceptor$1.proceedWithInvocation(TransactionInterceptor.java:123) [spring-tx-5.3.18.jar!/:5.3.18]
    at org.springframework.transaction.interceptor.TransactionAspectSupport.invokeWithinTransaction(TransactionAspectSupport.java:388) [spring-tx-5.3.18.jar!/:5.3.18]
    at org.springframework.transaction.interceptor.TransactionInterceptor.invoke(TransactionInterceptor.java:119) [spring-tx-5.3.18.jar!/:5.3.18]
    at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:186) [spring-aop-5.3.18.jar!/:5.3.18]
    at org.springframework.aop.framework.CglibAopProxy$CglibMethodInvocation.proceed(CglibAopProxy.java:753) [spring-aop-5.3.18.jar!/:5.3.18]
    at org.springframework.aop.framework.CglibAopProxy$DynamicAdvisedInterceptor.intercept(CglibAopProxy.java:698) [spring-aop-5.3.18.jar!/:5.3.18]
    at alfio.manager.NotificationManager$$EnhancerBySpringCGLIB$$4560cd7f.sendWaitingMessages(<generated>) [classes!/:?]
    at alfio.job.Jobs.sendEmails(Jobs.java:114) [classes!/:?]
    at jdk.internal.reflect.GeneratedMethodAccessor99.invoke(Unknown Source) ~[?:?]
    at jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:?]
    at java.lang.reflect.Method.invoke(Method.java:568) ~[?:?]
    at org.springframework.scheduling.support.ScheduledMethodRunnable.run(ScheduledMethodRunnable.java:84) [spring-context-5.3.18.jar!/:5.3.18]
    at org.springframework.scheduling.support.DelegatingErrorHandlingRunnable.run(DelegatingErrorHandlingRunnable.java:54) [spring-context-5.3.18.jar!/:5.3.18]
    at java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:539) [?:?]
    at java.util.concurrent.FutureTask.runAndReset(FutureTask.java:305) [?:?]
    at java.util.concurrent.ScheduledThreadPoolExecutor$ScheduledFutureTask.run(ScheduledThreadPoolExecutor.java:305) [?:?]
    at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1136) [?:?]
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:635) [?:?]
    at java.lang.Thread.run(Thread.java:833) [?:?]

[cbellone]

this might help: #1029 (comment)

[tobsowo]

I'll give it a try and check back. Currently away from my desk.

[tobsowo]

Thank you, it worked.