Email Settings using Gmail

troubleshooting
1

Hello team,

Kindly am getting and error when trying to send email notification using Gmail configuration. I’m using openboxes-config.properties for configuration

grails.mail.enabled=true
grails.mail.debug=true
grails.mail.from=xxxx@gmail.com
grails.mail.host=smtp.gmail.com
grails.mail.port=587
grails.mail.username=xxxxxx@gmail.com
grails.mail.password=password

grails.mail.props.mail.smtp.auth=true
grails.mail.props.mail.smtp.starttls.enable=true
grails.mail.props.mail.smtp.starttls.required=true
grails.mail.props.mail.smtp.ssl.protocols=TLSv1.2
grails.mail.props.mail.smtp.ssl.trust=smtp.gmail.com
grails.mail.props.mail.smtp.socketFactory.class=javax.net.ssl.SSLSocketFactory
grails.mail.props.mail.smtp.socketFactory.fallback=false

am getting this error :

DEBUG: Jakarta Mail version 1.6.7
DEBUG: successfully loaded resource: /META-INF/javamail.default.providers
DEBUG: Tables of loaded providers
DEBUG: Providers Listed By Class Name: {com.sun.mail.smtp.SMTPTransport=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle], com.sun.mail.imap.IMAPSSLStore=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Oracle], com.sun.mail.pop3.POP3Store=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Oracle], com.sun.mail.smtp.SMTPSSLTransport=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Oracle], com.sun.mail.imap.IMAPStore=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Oracle], com.sun.mail.pop3.POP3SSLStore=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Oracle]}
DEBUG: Providers Listed By Protocol: {imap=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Oracle], smtp=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle], pop3=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Oracle], imaps=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Oracle], smtps=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Oracle], pop3s=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Oracle]}
DEBUG: successfully loaded resource: /META-INF/javamail.default.address.map
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=tomcat, password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 smtp.gmail.com ESMTP 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587
EHLO vmi1450870.contaboserver.net
250-smtp.gmail.com at your service, [195.26.255.138]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
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 "STARTTLS", arg ""
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: use8bit false
MAIL FROM:<xxxxx@gmail.com>
530-5.7.0 Must issue a STARTTLS command first. For more information, go to
530-5.7.0  https://support.google.com/a/answer/3221692 and review RFC 3207
530 5.7.0 specifications. 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp
DEBUG SMTP: got response code 530, with response: 530-5.7.0 Must issue a STARTTLS command first. For more information, go to
530-5.7.0  https://support.google.com/a/answer/3221692 and review RFC 3207
530 5.7.0 specifications. 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp

RSET
250 2.1.5 Flushed 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp
DEBUG SMTP: MessagingException while sending, THROW: 
com.sun.mail.smtp.SMTPSendFailedException: 530-5.7.0 Must issue a STARTTLS command first. For more information, go to
530-5.7.0  https://support.google.com/a/answer/3221692 and review RFC 3207
530 5.7.0 specifications. 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - 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 javax.mail.Transport.send0(Transport.java:231)
	at javax.mail.Transport.send(Transport.java:100)
	at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1459)
	at org.apache.commons.mail.Email.send(Email.java:1496)
	at org.apache.commons.mail.Email$send$5.call(Unknown Source)
	at org.pih.warehouse.core.MailService.doSendMail(MailService.groovy:204)
	at org.pih.warehouse.core.MailService$doSendMail.callCurrent(Unknown Source)
	at org.pih.warehouse.core.MailService.sendMail(MailService.groovy:64)
	at org.pih.warehouse.core.MailService$sendMail$0.call(Unknown Source)
	at org.pih.warehouse.admin.AdminController$_sendMail_closure4.doCall(AdminController.groovy:128)
	at org.pih.warehouse.admin.AdminController$_sendMail_closure4.doCall(AdminController.groovy)
	at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
	at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62)
	at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
	at java.lang.reflect.Method.invoke(Method.java:498)
	at org.codehaus.groovy.reflection.CachedMethod.invoke(CachedMethod.java:98)
	at groovy.lang.MetaMethod.doMethodInvoke(MetaMethod.java:325)
	at org.codehaus.groovy.runtime.metaclass.ClosureMetaClass.invokeMethod(ClosureMetaClass.java:264)
	at groovy.lang.MetaClassImpl.invokeMethod(MetaClassImpl.java:1034)
	at groovy.lang.Closure.call(Closure.java:420)
	at groovy.lang.Closure.call(Closure.java:414)
	at grails.artefact.Controller$Trait$Helper.withForm(Controller.groovy:272)
	at grails.artefact.Controller$Trait$Helper$withForm$2.call(Unknown Source)
	at org.pih.warehouse.admin.AdminController.withForm(AdminController.groovy)
	at grails.artefact.Controller$Trait$Helper.withForm(Controller.groovy:250)
	at grails.artefact.Controller$Trait$Helper$withForm$1.call(Unknown Source)
	at org.pih.warehouse.admin.AdminController.withForm(AdminController.groovy)
	at grails.artefact.Controller$withForm$0.callCurrent(Unknown Source)
	at org.pih.warehouse.admin.AdminController.sendMail(AdminController.groovy:104)
	at org.grails.core.DefaultGrailsControllerClass$MethodHandleInvoker.invoke(DefaultGrailsControllerClass.java:223)
	at org.grails.core.DefaultGrailsControllerClass.invoke(DefaultGrailsControllerClass.java:188)
	at org.grails.web.mapping.mvc.UrlMappingsInfoHandlerAdapter.handle(UrlMappingsInfoHandlerAdapter.groovy:90)
	at org.springframework.web.servlet.DispatcherServlet.doDispatch(DispatcherServlet.java:967)
	at org.springframework.web.servlet.DispatcherServlet.doService(DispatcherServlet.java:901)
	at org.springframework.web.servlet.FrameworkServlet.processRequest(FrameworkServlet.java:970)
	at org.springframework.web.servlet.FrameworkServlet.doPost(FrameworkServlet.java:872)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:555)
	at org.springframework.web.servlet.FrameworkServlet.service(FrameworkServlet.java:846)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:199)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at io.sentry.spring.SentrySpringFilter.doFilterInternal(SentrySpringFilter.java:76)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.web.filter.ApplicationContextHeaderFilter.doFilterInternal(ApplicationContextHeaderFilter.java:54)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.actuate.trace.WebRequestTraceFilter.doFilterInternal(WebRequestTraceFilter.java:111)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.grails.web.servlet.mvc.GrailsWebRequestFilter.doFilterInternal(GrailsWebRequestFilter.java:77)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.grails.web.filters.HiddenHttpMethodFilter.doFilterInternal(HiddenHttpMethodFilter.java:67)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.web.filter.CharacterEncodingFilter.doFilterInternal(CharacterEncodingFilter.java:197)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at io.sentry.spring.tracing.SentryTracingFilter.doFilterInternal(SentryTracingFilter.java:91)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.web.filter.CorsFilter.doFilterInternal(CorsFilter.java:96)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.actuate.autoconfigure.MetricsFilter.doFilterInternal(MetricsFilter.java:100)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.web.support.ErrorPageFilter.doFilter(ErrorPageFilter.java:128)
	at org.springframework.boot.web.support.ErrorPageFilter.access$000(ErrorPageFilter.java:66)
	at org.springframework.boot.web.support.ErrorPageFilter$1.doFilterInternal(ErrorPageFilter.java:103)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.springframework.boot.web.support.ErrorPageFilter.doFilter(ErrorPageFilter.java:121)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:168)
	at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:90)
	at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:482)
	at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:130)
	at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:93)
	at org.apache.catalina.valves.AbstractAccessLogValve.invoke(AbstractAccessLogValve.java:660)
	at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:74)
	at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:346)
	at org.apache.coyote.http11.Http11Processor.service(Http11Processor.java:396)
	at org.apache.coyote.AbstractProcessorLight.process(AbstractProcessorLight.java:63)
	at org.apache.coyote.AbstractProtocol$ConnectionHandler.process(AbstractProtocol.java:937)
	at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.doRun(NioEndpoint.java:1793)
	at org.apache.tomcat.util.net.SocketProcessorBase.run(SocketProcessorBase.java:52)
	at org.apache.tomcat.util.threads.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1190)
	at org.apache.tomcat.util.threads.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:659)
	at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:63)
	at java.lang.Thread.run(Thread.java:750)
QUIT
221 2.0.0 closing connection 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp
2025-03-27 09:19:32,961 ERROR [http-nio-8181-exec-1] org.pih.warehouse.core.MailService: could not send email with subject 'Test email' to [******@****.org] from ******@gmail.com via smtp.gmail.com:587
org.apache.commons.mail.EmailException: Sending the email to the following server failed : smtp.gmail.com:587
	at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1469)
	at org.apache.commons.mail.Email.send(Email.java:1496)
	at org.apache.commons.mail.Email$send$5.call(Unknown Source)
	at org.pih.warehouse.core.MailService.doSendMail(MailService.groovy:204)
	at org.pih.warehouse.core.MailService$doSendMail.callCurrent(Unknown Source)
	at org.pih.warehouse.core.MailService.sendMail(MailService.groovy:64)
	at org.pih.warehouse.core.MailService$sendMail$0.call(Unknown Source)
	at org.pih.warehouse.admin.AdminController$_sendMail_closure4.doCall(AdminController.groovy:128)
	at org.pih.warehouse.admin.AdminController$_sendMail_closure4.doCall(AdminController.groovy)
	at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
	at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62)
	at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
	at java.lang.reflect.Method.invoke(Method.java:498)
	at org.codehaus.groovy.reflection.CachedMethod.invoke(CachedMethod.java:98)
	at groovy.lang.MetaMethod.doMethodInvoke(MetaMethod.java:325)
	at org.codehaus.groovy.runtime.metaclass.ClosureMetaClass.invokeMethod(ClosureMetaClass.java:264)
	at groovy.lang.MetaClassImpl.invokeMethod(MetaClassImpl.java:1034)
	at groovy.lang.Closure.call(Closure.java:420)
	at groovy.lang.Closure.call(Closure.java:414)
	at grails.artefact.Controller$Trait$Helper.withForm(Controller.groovy:272)
	at grails.artefact.Controller$Trait$Helper$withForm$2.call(Unknown Source)
	at org.pih.warehouse.admin.AdminController.withForm(AdminController.groovy)
	at grails.artefact.Controller$Trait$Helper.withForm(Controller.groovy:250)
	at grails.artefact.Controller$Trait$Helper$withForm$1.call(Unknown Source)
	at org.pih.warehouse.admin.AdminController.withForm(AdminController.groovy)
	at grails.artefact.Controller$withForm$0.callCurrent(Unknown Source)
	at org.pih.warehouse.admin.AdminController.sendMail(AdminController.groovy:104)
	at org.grails.core.DefaultGrailsControllerClass$MethodHandleInvoker.invoke(DefaultGrailsControllerClass.java:223)
	at org.grails.core.DefaultGrailsControllerClass.invoke(DefaultGrailsControllerClass.java:188)
	at org.grails.web.mapping.mvc.UrlMappingsInfoHandlerAdapter.handle(UrlMappingsInfoHandlerAdapter.groovy:90)
	at org.springframework.web.servlet.DispatcherServlet.doDispatch(DispatcherServlet.java:967)
	at org.springframework.web.servlet.DispatcherServlet.doService(DispatcherServlet.java:901)
	at org.springframework.web.servlet.FrameworkServlet.processRequest(FrameworkServlet.java:970)
	at org.springframework.web.servlet.FrameworkServlet.doPost(FrameworkServlet.java:872)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:555)
	at org.springframework.web.servlet.FrameworkServlet.service(FrameworkServlet.java:846)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:199)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at io.sentry.spring.SentrySpringFilter.doFilterInternal(SentrySpringFilter.java:76)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.web.filter.ApplicationContextHeaderFilter.doFilterInternal(ApplicationContextHeaderFilter.java:54)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.actuate.trace.WebRequestTraceFilter.doFilterInternal(WebRequestTraceFilter.java:111)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.grails.web.servlet.mvc.GrailsWebRequestFilter.doFilterInternal(GrailsWebRequestFilter.java:77)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.grails.web.filters.HiddenHttpMethodFilter.doFilterInternal(HiddenHttpMethodFilter.java:67)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.web.filter.CharacterEncodingFilter.doFilterInternal(CharacterEncodingFilter.java:197)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at io.sentry.spring.tracing.SentryTracingFilter.doFilterInternal(SentryTracingFilter.java:91)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.web.filter.CorsFilter.doFilterInternal(CorsFilter.java:96)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.actuate.autoconfigure.MetricsFilter.doFilterInternal(MetricsFilter.java:100)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.springframework.boot.web.support.ErrorPageFilter.doFilter(ErrorPageFilter.java:128)
	at org.springframework.boot.web.support.ErrorPageFilter.access$000(ErrorPageFilter.java:66)
	at org.springframework.boot.web.support.ErrorPageFilter$1.doFilterInternal(ErrorPageFilter.java:103)
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:107)
	at org.springframework.boot.web.support.ErrorPageFilter.doFilter(ErrorPageFilter.java:121)
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:168)
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:144)
	at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:168)
	at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:90)
	at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:482)
	at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:130)
	at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:93)
	at org.apache.catalina.valves.AbstractAccessLogValve.invoke(AbstractAccessLogValve.java:660)
	at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:74)
	at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:346)
	at org.apache.coyote.http11.Http11Processor.service(Http11Processor.java:396)
	at org.apache.coyote.AbstractProcessorLight.process(AbstractProcessorLight.java:63)
	at org.apache.coyote.AbstractProtocol$ConnectionHandler.process(AbstractProtocol.java:937)
	at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.doRun(NioEndpoint.java:1793)
	at org.apache.tomcat.util.net.SocketProcessorBase.run(SocketProcessorBase.java:52)
	at org.apache.tomcat.util.threads.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1190)
	at org.apache.tomcat.util.threads.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:659)
	at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:63)
	at java.lang.Thread.run(Thread.java:750)
Caused by: com.sun.mail.smtp.SMTPSendFailedException: 530-5.7.0 Must issue a STARTTLS command first. For more information, go to
530-5.7.0  https://support.google.com/a/answer/3221692 and review RFC 3207
530 5.7.0 specifications. 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - 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 javax.mail.Transport.send0(Transport.java:231)
	at javax.mail.Transport.send(Transport.java:100)
	at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1459)
	... 101 common frames omitted

Edited by @jmiranda to include code formatting and redact email addresses for privacy reasons.

2

Hey @faith_chepkoech

Thanks for the message.

I was chatting with another user about this the other day and realized we might not currently support Google SMTP for outbound mail. That user was going to investigate, so I’ll reach out to them to see if there’s an easy fix.

However, until we can implement Google SMTP support, I would recommend using a transactional mail service like Amazon SES, SendGrid, MailGun, etc. Most of these provide a free tier, so hopefully the cost is negligible or zero.

Thanks for including your configuration. I’ll do some investigation myself using these settings with my own Google account to see if there’s an easy fix (i.e. maybe we just need to make sure we set the mail props on the smtp client we’re using).

Justin

3

@faith_chepkoech What version of OpenBoxes are you using?

4

Ok, so I tested the Google SMTP server locally and it works fine with the following configuration. However, make sure the config is copied into openboxes-config.groovy. You can continue to use openboxes-config.properties for your other OpenBoxes configuration, but more advanced config (i.e. grails.mail.props) does not get parsed properly when it’s located in the openboxes-config.properties file.

grails {
    mail {
        enabled = true
        debug = true
        host = "smtp.gmail.com"
        port = 587
        username = "user@gmail.com"
        password = "<password>"
        from = "info@openboxes.com"
        props = ["mail.smtp.auth":"true", "mail.smtp.starttls.enable":"true", "mail.smtp.port":"587"]
    }
}

Back when I first set this up on my development machine, Google would not let me use my account password as the auth password, instead requiring an App Password.

An app password is a 16-digit passcode that gives a less secure app or device permission to access your Google Account. App passwords can only be used with accounts that have 2-Step Verification turned on.

According to the following article (Sign in with app passwords - Google Account Help), it seems that App Passwords are no longer required so you should be able to use your default Gmail password. If you encounter any issues with authenticating let us know and we can try to troubleshoot.

5

@jmiranda am using version 0.9.3

6

@jmiranda Thank you for the guidance, but i tried with this config but still getting the same error.

7

It’s the exact same error like the one you shared previously?

530-5.7.0 Must issue a STARTTLS command first. For more information, go to
530-5.7.0  https://support.google.com/a/answer/3221692 and review RFC 3207
530 5.7.0 specifications. 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp
DEBUG SMTP: got response code 530, with response: 530-5.7.0 Must issue a STARTTLS command first. For more information, go to
530-5.7.0  https://support.google.com/a/answer/3221692 and review RFC 3207
530 5.7.0 specifications. 6a1803df08f44-6eb3ef340f7sm76718026d6.51 - gsmtp

Or does it include a different error message? For example, this is what I started seeing when the STARTTLS config was being picked up by the application.

Caused by: javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. For more information, go to
535 5.7.8  https://support.google.com/mail/?p=BadCredentials 6a1803df08f44-6eec964649fsm3812706d6.40 - gsmtp

Once I set the username/password properly, it all started working for me.

In any case, can you send all of your configuration files (with credentials redacted) and the catalina.out file to support@openboxes.com so that I can try to reproduce the error on my side.

If you’re still seeing the first error, I think that’s just a matter of the configuration not being picked up by the application.

8

Ignore my question. While investigating this issue, I forgot that I hard-coded the StartTLSEnabled setting.

    //if (startTlsEnabled) {
    //    email.setStartTLSEnabled(startTlsEnabled)
    //}
    email.setStartTLSEnabled(true)

So I think the issue is with the starttls configuration. For some reason, this method always returns false no matter what the configuration looks like.

    Boolean getStartTlsEnabled() {
        return grailsApplication.config.grails.mail.props["mail.smtp.starttls.enable"]
    }

I’ll keep digging into it, but again it would be best to use any of the other transactional email services besides Google SMTP.

9

I’ve created a ticket for this one in case you want to keep track of the progress. I’ll post back here when it’s fixed.

10

Thanks @jmiranda ,
Looking forward.