[MGNLMAIL-104] Unable to send email through Gmail Created: 16/Jan/20  Updated: 02/Jun/22  Resolved: 16/Mar/21

Status: Closed
Project: Magnolia Mail Module
Component/s: None
Affects Version/s: 5.5.2
Fix Version/s: None

Type: Bug Priority: Neutral
Reporter: Richard Gange Assignee: Unassigned
Resolution: Workaround exists Votes: 0
Labels: None
Remaining Estimate: 0d
Time Spent: 3h
Original Estimate: Not Specified

Attachments: PNG File error.png     PNG File mail-ch-verify.png     PNG File mail-ch.png     PNG File mail.png     PNG File oauth-2.png    
Issue Links:
Relates
relates to DOCU-2045 DOC: Example of how to use OAuth 2.0 Closed
relates to MGNLMAIL-77 Add possibility for SMTP Session debu... Closed
causality
relation
is related to MGNLMAIL-100 Cannot verify the current mail settin... Closed
is related to MGNLMAIL-66 Implement OAuth 2.0 authentication Closed
Template:
Acceptance criteria:
Empty
Task DoD:
[ ]* Doc/release notes changes? Comment present?
[ ]* Downstream builds green?
[ ]* Solution information and context easily available?
[ ]* Tests
[ ]* FixVersion filled and not yet released
[ ]  Architecture Decision Record (ADR)
Bug DoR:
[ ]* Steps to reproduce, expected, and actual results filled
[ ]* Affected version filled
Date of First Response:

 Description   

My settings:

Also tried with port 587 and STARTTLS

The UI displayed error:

The stack trace:

2020-01-16 09:58:34,298 ERROR agnolia.module.mail.app.verify.MailVerifyPresenter: Unable to send email.
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 x11sm29004659wre.68 - gsmtp

	at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:932) ~[javax.mail-1.5.6.jar:1.5.6]
	at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:843) ~[javax.mail-1.5.6.jar:1.5.6]
	at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:748) ~[javax.mail-1.5.6.jar:1.5.6]
	at javax.mail.Service.connect(Service.java:388) ~[javax.mail-1.5.6.jar:1.5.6]
	at javax.mail.Service.connect(Service.java:246) ~[javax.mail-1.5.6.jar:1.5.6]
	at javax.mail.Service.connect(Service.java:195) ~[javax.mail-1.5.6.jar:1.5.6]
	at javax.mail.Transport.send0(Transport.java:254) ~[javax.mail-1.5.6.jar:1.5.6]
	at javax.mail.Transport.send(Transport.java:124) ~[javax.mail-1.5.6.jar:1.5.6]
	at info.magnolia.module.mail.handlers.SimpleMailHandler.sendMail(SimpleMailHandler.java:60) ~[magnolia-module-mail-5.5.2.jar:?]
	at info.magnolia.module.mail.app.verify.MailVerifyPresenter.sendTemplateMail(MailVerifyPresenter.java:249) [magnolia-module-mail-5.5.2.jar:?]
	at info.magnolia.module.mail.app.verify.MailVerifyViewImpl$2.buttonClick(MailVerifyViewImpl.java:86) [magnolia-module-mail-5.5.2.jar:?]
	at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[?:1.8.0_181]
	at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62) ~[?:1.8.0_181]
	at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:1.8.0_181]
	at java.lang.reflect.Method.invoke(Method.java:498) ~[?:1.8.0_181]
	at com.vaadin.event.ListenerMethod.receiveEvent(ListenerMethod.java:499) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.event.EventRouter.fireEvent(EventRouter.java:273) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.event.EventRouter.fireEvent(EventRouter.java:237) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.AbstractClientConnector.fireEvent(AbstractClientConnector.java:1014) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.ui.Button.fireClick(Button.java:384) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.ui.Button$1.click(Button.java:57) [vaadin-server-8.4.2.jar:8.4.2]
	at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[?:1.8.0_181]
	at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62) ~[?:1.8.0_181]
	at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:1.8.0_181]
	at java.lang.reflect.Method.invoke(Method.java:498) ~[?:1.8.0_181]
	at com.vaadin.server.ServerRpcManager.applyInvocation(ServerRpcManager.java:155) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.ServerRpcManager.applyInvocation(ServerRpcManager.java:116) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.communication.ServerRpcHandler.handleInvocation(ServerRpcHandler.java:445) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.communication.ServerRpcHandler.handleInvocations(ServerRpcHandler.java:410) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.communication.ServerRpcHandler.handleRpc(ServerRpcHandler.java:274) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.communication.UidlRequestHandler.synchronizedHandleRequest(UidlRequestHandler.java:90) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.SynchronizedRequestHandler.handleRequest(SynchronizedRequestHandler.java:40) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.VaadinService.handleRequest(VaadinService.java:1601) [vaadin-server-8.4.2.jar:8.4.2]
	at com.vaadin.server.VaadinServlet.service(VaadinServlet.java:445) [vaadin-server-8.4.2.jar:8.4.2]
	at info.magnolia.ui.admincentral.AdmincentralVaadinServlet.service(AdmincentralVaadinServlet.java:141) [magnolia-ui-admincentral-5.7.5.jar:?]
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:731) [servlet-api.jar:?]
	at info.magnolia.cms.filters.ServletDispatchingFilter.doFilter(ServletDispatchingFilter.java:148) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.CompositeFilter.doFilter(CompositeFilter.java:65) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.virtualuri.VirtualUriFilter.doFilter(VirtualUriFilter.java:98) [magnolia-virtual-uri-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.module.cache.executor.Bypass.processCacheRequest(Bypass.java:58) [magnolia-cache-core-5.6.2.jar:?]
	at info.magnolia.module.cache.executor.CompositeExecutor.processCacheRequest(CompositeExecutor.java:67) [magnolia-cache-core-5.6.2.jar:?]
	at info.magnolia.module.cache.filter.CacheFilter.doFilter(CacheFilter.java:220) [magnolia-cache-core-5.6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.i18n.I18nContentSupportFilter.doFilter(I18nContentSupportFilter.java:89) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.RangeSupportFilter.doFilter(RangeSupportFilter.java:77) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.security.BaseSecurityFilter.doFilter(BaseSecurityFilter.java:57) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.security.SecurityCallbackFilter.doFilter(SecurityCallbackFilter.java:84) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.security.LogoutFilter.doFilter(LogoutFilter.java:94) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.module.site.filters.SiteMergeFilter.doFilter(SiteMergeFilter.java:119) [magnolia-site-1.2.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.multisite.filters.MultiSiteFilter.doFilter(MultiSiteFilter.java:120) [magnolia-module-multisite-1.3.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MultiChannelFilter.doFilter(MultiChannelFilter.java:83) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.module.cache.filter.GZipFilter.doFilter(GZipFilter.java:73) [magnolia-cache-core-5.6.2.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.security.auth.login.LoginFilter.doFilter(LoginFilter.java:127) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.enterprise.registration.RegistrationFilter.doFilter(RegistrationFilter.java:75) [magnolia-module-enterprise-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.personalization.preview.filter.PreviewFilter.doFilter(PreviewFilter.java:92) [magnolia-personalization-preview-app-1.6.2.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.ContentTypeFilter.doFilter(ContentTypeFilter.java:155) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.ContextFilter.doFilter(ContextFilter.java:128) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.CompositeFilter.doFilter(CompositeFilter.java:65) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.SafeDestroyMgnlFilterWrapper.doFilter(SafeDestroyMgnlFilterWrapper.java:107) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlFilterDispatcher.doDispatch(MgnlFilterDispatcher.java:67) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlMainFilter.doFilter(MgnlMainFilter.java:110) [magnolia-core-5.7.5.jar:?]
	at info.magnolia.cms.filters.MgnlMainFilter.doFilter(MgnlMainFilter.java:96) [magnolia-core-5.7.5.jar:?]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241) [catalina.jar:7.0.82]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208) [catalina.jar:7.0.82]
	at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:219) [catalina.jar:7.0.82]
	at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:110) [catalina.jar:7.0.82]
	at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:169) [catalina.jar:7.0.82]
	at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:103) [catalina.jar:7.0.82]
	at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:962) [catalina.jar:7.0.82]
	at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:116) [catalina.jar:7.0.82]
	at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:445) [catalina.jar:7.0.82]
	at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1115) [tomcat-coyote.jar:7.0.82]
	at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:637) [tomcat-coyote.jar:7.0.82]
	at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:318) [tomcat-coyote.jar:7.0.82]
	at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1149) [?:1.8.0_181]
	at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:624) [?:1.8.0_181]
	at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:61) [tomcat-coyote.jar:7.0.82]
	at java.lang.Thread.run(Thread.java:748) [?:1.8.0_181]


 Comments   
Comment by Richard Gange [ 16/Jan/20 ]

I am able to get it working using mail.ch server.

Here are the settings:

Two things to also change:

  • The superuser needs an email address with the mail.ch domain
  • On the Verify setup subapp, the top two options do not work. See MGNLMAIL-100. You can use the freemarker template to verify but you will need to set the from address here: /modules/mail/config/templatesConfiguration/testFreemarker@from

The shared services emails can be used for testing. See https://wiki.magnolia-cms.com/display/SERVICESINT/Recommended+software#Recommendedsoftware-Sharedaccounts
services.magnolia.cms@mail.ch

Comment by Richard Gange [ 16/Jan/20 ]

It seems to me that for Gmail we will need to use the OAuth 2.0 settings. However, how that is configured is unclear. I got my credentials.json file from Google. In there I have client_id and a client_secret. I don't have a refresh token. Instead in my creds file I have a token URI.

{ 
    "web":{ 
        "client_id":"766218068210-vpuii9cdqdhkstgpkjj7vct3ohk889kj.apps.googleusercontent.com",
        "project_id":"my-project-1579095564324",
        "auth_uri":"https://accounts.google.com/o/oauth2/auth",
        "token_uri":"https://oauth2.googleapis.com/token",
        "auth_provider_x509_cert_url":"https://www.googleapis.com/oauth2/v1/certs",
        "client_secret":"xxxxxxxxxxxxxxxxxxxxxxxxxx"
    }
}

Comment by Richard Gange [ 04/May/20 ]

After adding MGNLMAIL-77

2020-05-04 18:29:59,343 DEBUG info.magnolia.module.mail.MailTemplate            : Setting javax.mail.Session to debug
DEBUG: setDebug: JavaMail version 1.6.2
2020-05-04 18:29:59,344 DEBUG info.magnolia.module.mail.templates.MgnlEmail     : Set attachments [0] for mail: [info.magnolia.module.mail.templates.impl.FreemarkerEmail]
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: need username and password for authentication
DEBUG SMTP: protocolConnect returning false, host=smtp.gmail.com, user=richard.gange@magnolia-cms.com, password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 465, isSSL true
220 smtp.gmail.com ESMTP m188sm14448004wme.47 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 465
EHLO localhost
250-smtp.gmail.com at your service, [31.10.141.65]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
DEBUG SMTP: Found extension "SMTPUTF8", arg ""
DEBUG SMTP: protocolConnect login, host=smtp.gmail.com, user=richard.gange@magnolia-cms.com, password=<non-null>
DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2 
DEBUG SMTP: Using mechanism LOGIN
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN failed
2020-05-04 18:29:59,897 ERROR agnolia.module.mail.app.verify.MailVerifyPresenter: Unable to send email.
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 m188sm14448004wme.47 - gsmtp

	at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:965) ~[javax.mail-1.6.2.jar:1.6.2]
	at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:876) ~[javax.mail-1.6.2.jar:1.6.2]
	at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:780) ~[javax.mail-1.6.2.jar:1.6.2]
	at javax.mail.Service.connect(Service.java:388) ~[javax.mail-1.6.2.jar:1.6.2]
	at javax.mail.Service.connect(Service.java:246) ~[javax.mail-1.6.2.jar:1.6.2]
	at javax.mail.Service.connect(Service.java:195) ~[javax.mail-1.6.2.jar:1.6.2]
	at javax.mail.Transport.send0(Transport.java:254) ~[javax.mail-1.6.2.jar:1.6.2]
	at javax.mail.Transport.send(Transport.java:124) ~[javax.mail-1.6.2.jar:1.6.2]
	at info.magnolia.module.mail.handlers.SimpleMailHandler.sendMail(SimpleMailHandler.java:60) ~[magnolia-module-mail-5.5.4-SNAPSHOT.jar:?]
	at info.magnolia.module.mail.app.verify.MailVerifyPresenter.sendTemplateMail(MailVerifyPresenter.java:249) [magnolia-module-mail-5.5.4-SNAPSHOT.jar:?]
	at info.magnolia.module.mail.app.verify.MailVerifyViewImpl$2.buttonClick(MailVerifyViewImpl.java:86) [magnolia-module-mail-5.5.4-SNAPSHOT.jar:?]
	at sun.reflect.GeneratedMethodAccessor406.invoke(Unknown Source) ~[?:?]
	at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:1.8.0_181]
	at java.lang.reflect.Method.invoke(Method.java:498) ~[?:1.8.0_181]
	at com.vaadin.event.ListenerMethod.receiveEvent(ListenerMethod.java:499) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.event.EventRouter.fireEvent(EventRouter.java:273) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.event.EventRouter.fireEvent(EventRouter.java:237) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.AbstractClientConnector.fireEvent(AbstractClientConnector.java:1014) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.ui.Button.fireClick(Button.java:384) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.ui.Button$1.click(Button.java:57) [vaadin-server-8.9.4.jar:8.9.4]
	at sun.reflect.GeneratedMethodAccessor405.invoke(Unknown Source) ~[?:?]
	at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:1.8.0_181]
	at java.lang.reflect.Method.invoke(Method.java:498) ~[?:1.8.0_181]
	at com.vaadin.server.ServerRpcManager.applyInvocation(ServerRpcManager.java:155) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.ServerRpcManager.applyInvocation(ServerRpcManager.java:116) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.communication.ServerRpcHandler.handleInvocation(ServerRpcHandler.java:445) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.communication.ServerRpcHandler.handleInvocations(ServerRpcHandler.java:410) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.communication.ServerRpcHandler.handleRpc(ServerRpcHandler.java:274) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.communication.UidlRequestHandler.synchronizedHandleRequest(UidlRequestHandler.java:90) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.SynchronizedRequestHandler.handleRequest(SynchronizedRequestHandler.java:40) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.VaadinService.handleRequest(VaadinService.java:1602) [vaadin-server-8.9.4.jar:8.9.4]
	at com.vaadin.server.VaadinServlet.service(VaadinServlet.java:448) [vaadin-server-8.9.4.jar:8.9.4]
	at info.magnolia.admincentral.AdmincentralServlet.service(AdmincentralServlet.java:119) [magnolia-admincentral-6.2.jar:?]
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:741) [servlet-api.jar:?]
	at info.magnolia.cms.filters.ServletDispatchingFilter.doFilter(ServletDispatchingFilter.java:148) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.CompositeFilter.doFilter(CompositeFilter.java:65) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.virtualuri.VirtualUriFilter.doFilter(VirtualUriFilter.java:98) [magnolia-virtual-uri-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.module.cache.executor.Bypass.processCacheRequest(Bypass.java:58) [magnolia-cache-core-5.9.0.jar:?]
	at info.magnolia.module.cache.executor.CompositeExecutor.processCacheRequest(CompositeExecutor.java:66) [magnolia-cache-core-5.9.0.jar:?]
	at info.magnolia.module.cache.filter.CacheFilter.doFilter(CacheFilter.java:164) [magnolia-cache-core-5.9.0.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.i18n.I18nContentSupportFilter.doFilter(I18nContentSupportFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.RangeSupportFilter.doFilter(RangeSupportFilter.java:78) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.security.BaseSecurityFilter.doFilter(BaseSecurityFilter.java:57) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.security.SecurityCallbackFilter.doFilter(SecurityCallbackFilter.java:84) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.security.LogoutFilter.doFilter(LogoutFilter.java:94) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.module.site.filters.SiteMergeFilter.doFilter(SiteMergeFilter.java:119) [magnolia-site-1.2.4.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.multisite.filters.MultiSiteFilter.doFilter(MultiSiteFilter.java:120) [magnolia-module-multisite-2.1.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MultiChannelFilter.doFilter(MultiChannelFilter.java:83) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.module.cache.filter.GZipFilter.doFilter(GZipFilter.java:74) [magnolia-cache-core-5.9.0.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.security.auth.login.LoginFilter.doFilter(LoginFilter.java:127) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.enterprise.registration.RegistrationFilter.doFilter(RegistrationFilter.java:79) [magnolia-module-enterprise-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.personalization.preview.filter.PreviewFilter.doFilter(PreviewFilter.java:92) [magnolia-personalization-preview-app-2.0.jar:?]
	at info.magnolia.cms.filters.OncePerRequestAbstractMgnlFilter.doFilter(OncePerRequestAbstractMgnlFilter.java:59) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:81) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.ContentTypeFilter.doFilter(ContentTypeFilter.java:155) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.ContextFilter.doFilter(ContextFilter.java:128) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterChain.doFilter(MgnlFilterChain.java:79) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.CompositeFilter.doFilter(CompositeFilter.java:65) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.AbstractMgnlFilter.doFilter(AbstractMgnlFilter.java:85) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.SafeDestroyMgnlFilterWrapper.doFilter(SafeDestroyMgnlFilterWrapper.java:107) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlFilterDispatcher.doDispatch(MgnlFilterDispatcher.java:67) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlMainFilter.doFilter(MgnlMainFilter.java:110) [magnolia-core-6.2.jar:?]
	at info.magnolia.cms.filters.MgnlMainFilter.doFilter(MgnlMainFilter.java:96) [magnolia-core-6.2.jar:?]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:193) [catalina.jar:9.0.33]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:166) [catalina.jar:9.0.33]
	at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:202) [catalina.jar:9.0.33]
	at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:96) [catalina.jar:9.0.33]
	at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:541) [catalina.jar:9.0.33]
	at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:139) [catalina.jar:9.0.33]
	at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:92) [catalina.jar:9.0.33]
	at org.apache.catalina.valves.AbstractAccessLogValve.invoke(AbstractAccessLogValve.java:688) [catalina.jar:9.0.33]
	at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:74) [catalina.jar:9.0.33]
	at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:343) [catalina.jar:9.0.33]
	at org.apache.coyote.http11.Http11Processor.service(Http11Processor.java:373) [tomcat-coyote.jar:9.0.33]
	at org.apache.coyote.AbstractProcessorLight.process(AbstractProcessorLight.java:65) [tomcat-coyote.jar:9.0.33]
	at org.apache.coyote.AbstractProtocol$ConnectionHandler.process(AbstractProtocol.java:868) [tomcat-coyote.jar:9.0.33]
	at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.doRun(NioEndpoint.java:1594) [tomcat-coyote.jar:9.0.33]
	at org.apache.tomcat.util.net.SocketProcessorBase.run(SocketProcessorBase.java:49) [tomcat-coyote.jar:9.0.33]
	at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1149) [?:1.8.0_181]
	at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:624) [?:1.8.0_181]
	at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:61) [tomcat-util.jar:9.0.33]
	at java.lang.Thread.run(Thread.java:748) [?:1.8.0_181]
Comment by Viet Nguyen [ 25/Jun/20 ]

From https://support.google.com/mail/?p=BadCredentials

If you can't sign in to your email client, you might see one of these errors:

  • "Username and password not accepted"
  • "Invalid credentials"
  • You're asked to enter your username and password over and over

Step 1: Check your password

If you have these problems or can’t sign in, first check to make sure you’re using the right password.

Step 2: Try these troubleshooting steps

  • Update your email client to the latest version.
  • Use an App Password: If you use 2-Step Verification, try signing in with an App Password.
  • Allow less secure apps: If you don't use 2-Step Verification, you might need to allow less secure apps to access your account.
  • If you recently changed your Gmail password, you might need to re-enter your Gmail account information or completely repeat your Gmail account setup on your other email client.
  • If the tips above didn't help, visit https://www.google.com/accounts/DisplayUnlockCaptcha and follow the steps on the page.
  • The email client's sign-in method might be insecure. Try signing in directly on the Gmail app.
  • Make sure your mail app isn't set to check for new email too frequently. If your mail app checks for new messages more than once every 10 minutes, the app’s access to your account could be blocked.
Comment by Richard Gange [ 16/Mar/21 ]

I am able to do it by using the Less Secure setting but it would be nice to have an example of using Gmail with an OAuth configuration. See DOCU-2045

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