Jenkins and Office365 email notification settings - email

Question

Environment:
Windows 2008 R2
Jenkins 1.580.2 LTS
Mailer plugin 1.12
Email Extension Plugin 2.39
Java 8
I have some problems with configuring my Jenkins CI server to send email notifications after moving to the Business account in Office365.
So here is the my configurations:
Jenkins is started with StartTLS support (with parameter
'-Dmail.smtp.starttls.enabled=true')
SMTP server is 'smtp.office365.com'
SMTP port is 587
SSL is disabled for SMTP authention
Account is real and password is correct
Account is specified like username#company.com
Looks like message should be sent correctly but the email message is NOT sent.
The following error occurs:
Failed to send out e-mail
com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2057)
at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1580)
at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1097)
at javax.mail.Transport.send0(Transport.java:195)
at javax.mail.Transport.send(Transport.java:124)
at hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:527)
at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source)
at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source)
at java.lang.reflect.Method.invoke(Unknown Source)
at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:298)
at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:161)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:96)
at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:121)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:745)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:875)
at org.kohsuke.stapler.MetaClass$6.doDispatch(MetaClass.java:249)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:745)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:875)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:648)
at org.kohsuke.stapler.Stapler.service(Stapler.java:237)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:848)
at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:686)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1494)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:96)
at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:58)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:99)
at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:88)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:48)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)
at hudson.security.UnwrapSecurityExceptionFilter.doFilter(UnwrapSecurityExceptionFilter.java:51)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at jenkins.security.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:117)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.providers.anonymous.AnonymousProcessingFilter.doFilter(AnonymousProcessingFilter.java:125)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.ui.rememberme.RememberMeProcessingFilter.doFilter(RememberMeProcessingFilter.java:142)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.ui.AbstractProcessingFilter.doFilter(AbstractProcessingFilter.java:271)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at jenkins.security.BasicHeaderProcessor.doFilter(BasicHeaderProcessor.java:86)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at org.acegisecurity.context.HttpSessionContextIntegrationFilter.doFilter(HttpSessionContextIntegrationFilter.java:249)
at hudson.security.HttpSessionContextIntegrationFilter2.doFilter(HttpSessionContextIntegrationFilter2.java:67)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)
at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:46)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:81)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1474)
at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:499)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:137)
at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:533)
at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:231)
at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1086)
at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:428)
at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:193)
at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1020)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:135)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:116)
at org.eclipse.jetty.server.Server.handle(Server.java:370)
at org.eclipse.jetty.server.AbstractHttpConnection.handleRequest(AbstractHttpConnection.java:489)
at org.eclipse.jetty.server.AbstractHttpConnection.content(AbstractHttpConnection.java:960)
at org.eclipse.jetty.server.AbstractHttpConnection$RequestHandler.content(AbstractHttpConnection.java:1021)
at org.eclipse.jetty.http.HttpParser.parseNext(HttpParser.java:865)
at org.eclipse.jetty.http.HttpParser.parseAvailable(HttpParser.java:235)
at org.eclipse.jetty.server.AsyncHttpConnection.handle(AsyncHttpConnection.java:82)
at org.eclipse.jetty.io.nio.SelectChannelEndPoint.handle(SelectChannelEndPoint.java:668)
at org.eclipse.jetty.io.nio.SelectChannelEndPoint$1.run(SelectChannelEndPoint.java:52)
at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)
at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
at java.lang.Thread.run(Unknown Source)
Could please someone help me with this?
Thank you

Answer 1

After review the answers here I still got the error:
Client does not have permissions to send as this sender
So what I missed is to set the System Admin e-mail address and than everything worked well - probably the email plugin using the System Admin e-mail to connect the mailbox .
Here are all the steps to configure the mail notification (also email ext):
Go to manage jenkins > configure system:
under Jenkins Location
System Admin e-mail address: notification#domain.com
under Extended E-mail Notification:
SMTP server: smtp.office365.com
Default user e-mail suffix: #domain.com
User Name: notification#domain.com
Password: ###########
Use SSL: no
SMTP Port: 25 or 587
Charset UTF-8
edit file: "/etc/default/jenkins"
sudo vim /etc/default/jenkins
add the line:
JAVA_ARGS="-Djava.awt.headless=true -Dmail.smtp.starttls.enable=true"
restart jenkins
sudo /etc/init.d/jenkins restart
tested on ubuntu 16

Answer 2

TLS is not enabled.
Just add next java property for Jenkins on start:
-Dmail.smtp.starttls.enable=true
So for Ubuntu it can be configured here:
home/ubuntu# grep ^JAVA_ARGS /etc/default/jenkins
JAVA_ARGS="-Djava.awt.headless=true -Dmail.smtp.starttls.enable=true"

Answer 3

I used SMTP port 25 instead of 587 and it works

Answer 4

If you are using AWS EC2 AMI Linux then this is a common problem. You need to edit /etc/sysconfig/jenkins and restart Jenkins.
You need to have both
JENKINS_JAVA_OPTIONS="-Djava.awt.headless=true -Dmail.smtp.starttls.enable=true"
AND
JENKINS_ARGS="-Dmail.smtp.starttls.enable=true"

Answer 5

Steps:
Open debug of your mail sender
Check if you have got the following in your first debug info.
DEBUG: setDebug: JavaMail version 1.3
Please upgrade your JavaMail version to one higher than 1.4 and it should be fixed without any code changes.

Answer 6

If you are using Jenkins in Kubernetes add below lines in your YAML file and make sure you have the same email in "System Admin e-mail address: "
containers:
...
env:
- name: JENKINS_OPTS
value: "-Dmail.smtp.starttls.enable=true"
- name: JENKINS_JAVA_OPTIONS
value: "-Djava.awt.headless=true -Dmail.smtp.starttls.enable=true"
- name: JAVA_OPTS
value: >-
-Djava.awt.headless=true
-Dmail.smtp.starttls.enable=true

Answer 7

According to my test, just the following parameters are required:
System Admin e-mail address: bunny#acme.com
SMTP server: smtp.office365.com
SMTP Port: 587
SMTP Username: bunny#acme.com
SMTP Password: ***
Use SSL: no
Charset UTF-8
And if you don't want to touch/restart your jenkins at low level (-Dmail.smtp.starttls.enable=true) just add
mail.smtp.starttls.enable = true to the Advanced Email Properties