Client does not have permissions to send as this sender (office 365, grails)

Question

I am continuously receiving following error message while trying to configure grails mail plugin (https://grails.org/plugin/mail) for grails spring security plugin.

Here is my configuration looks so far,

    grails {
        mail {
            host = "smtp.office365.com"
            port = 587
            username = "[email protected]"
            password = "password"
            props = ["mail.smtp.starttls.enable":"true",
                     "mail.smtp.port":"587"]
        }
    }

    grails.mail.default.from = "[email protected]"

And here is my stack-trace.

    .......| Error 2015-04-17 11:59:39,184 [http-bio-8080-exec-8] ERROR errors.GrailsExceptionResolver  - MailSendException occurred when processing request: [POST] /retouch/register/forgotPassword - parameters:
    username: customer
    Failed messages: com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.60 SMTP; Client does not have permissions to send as this sender
    . Stacktrace follows:
    Message: Failed messages: com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.60 SMTP; Client does not have permissions to send as this sender
        Line | Method
    ->>  131 | sendMessage    in grails.plugin.mail.MailMessageBuilder
    - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 
    |     55 | sendMail       in grails.plugin.mail.MailService
    |     59 | sendMail . . . in     ''
    |    156 | forgotPassword in grails.plugin.springsecurity.ui.RegisterController
    |    198 | doFilter . . . in grails.plugin.cache.web.filter.PageFragmentCachingFilter
    |     63 | doFilter       in grails.plugin.cache.web.filter.AbstractFilter
    |     53 | doFilter . . . in grails.plugin.springsecurity.web.filter.GrailsAnonymousAuthenticationFilter
    |     49 | doFilter       in grails.plugin.springsecurity.web.authentication.RequestHolderAuthenticationFilter
    |     82 | doFilter . . . in grails.plugin.springsecurity.web.authentication.logout.MutableLogoutFilter
    |   1145 | runWorker      in java.util.concurrent.ThreadPoolExecutor
    |    615 | run . . . . .  in java.util.concurrent.ThreadPoolExecutor$Worker
    ^    745 | run            in java.lang.Thread

Note: Problem is only find in Grails spring security plugin.

Answer 1

I ran into the exact same issue. Problem seems to arise due to spring security trying to set "from" attribute in the email as no-reply@localhost. Try adding these lines to the config file

 grails.plugin.springsecurity.ui.register.emailFrom = '[email protected]'
 grails.plugin.springsecurity.ui.forgotPassword.emailFrom = '[email protected]'

note: [email protected] is your office365 email

Answer 2

username = "[email protected]"

grails.mail.default.from = "[email protected]"

username email must equal to from email.

Answer 3

I got Grails sending email pretty easily using a test GMail account, but the code crashed with the error when I tried to send from an outlook.office365.com account:

Failed messages: com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.60 SMTP; Client does not have permissions to send as this sender

It turns out I was only missing this line:

grails.mail.default.from = "[email protected]"

Note the the email address specified in grails.mail.default.from must match the one in grails.mail.username .

Here is the configuration that worked for me. Base example is the Hubbub example from the book Grails in Action (2nd Ed):

grails.mail.default.from = "[email protected]"
grails {
  mail {  
      host = "outlook.office365.com"
      port = 587
      username = "[email protected]"
      password = "secret"
      props = [ "mail.smtp.starttls.enable" : "true",
                "mail.smtp.port"            : "587",
                "mail.smtp.debug"           : "true" ]
  }

and here is the corresponding email sending function:

def email() {
  println( "Sending email.." );
  sendMail {
      to "[email protected]"
      subject "[mail-test]"
      body ("This is a test email, time: " + new Date() )
  }
  println( "  success!!!" );
  flash.message = "Successfully sent email"
  redirect( uri: "/" );
}