problems configuring smtp

[Jeroen Bosch]

Hi,

I tried to configure the e-mail updates for our tickets. I tried to use a public smtp relay, but that results in errors like this one:

2015-12-22 16:58:27 [ERROR] Failed to send message
javax.mail.SendFailedException: Invalid Addresses;
  nested exception is:
    com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <address obscured>: Relay access denied
;
  nested exception is:
    com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <address obscured>: Relay access denied

    at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1885)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1133)
    at javax.mail.Transport.send0(Transport.java:254)
    at javax.mail.Transport.send(Transport.java:124)
    at com.gitblit.service.MailService.run(MailService.java:277)
    at java.util.concurrent.Executors$RunnableAdapter.call(Unknown Source)
    at java.util.concurrent.FutureTask.runAndReset(Unknown Source)
    at java.util.concurrent.ScheduledThreadPoolExecutor$ScheduledFutureTask.access$301(Unknown Source)
    at java.util.concurrent.ScheduledThreadPoolExecutor$ScheduledFutureTask.run(Unknown Source)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
    at java.lang.Thread.run(Unknown Source)
Caused by: com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <address obscured>: Relay access denied
...

I couldn't find much help on google/stack overflow, so I tried my personal gmail account for relay.

This doesn't work either, because google thinks 'the device' is not secure enough. I got the email indicating the blocked access, but I couldn't activate it in my gmail settings page.
In the logfile you get an javax.mail.AuthenticationFailedException 534-5.7.14, and a notice which directs you to your gmail settings.

Any ideas how to fix this? Or are there plans to 'upgrade' the mail component to be more secure?

[Jamey Graham]

does this help at all?

http://stackoverflow.com/questions/26736062/sending-email-fails-when-two-factor-authentication-is-on-for-gmail