Are the from address and reply to addresses valid addresses on the server?
Exchange will deny if authentication fails and so it can't verify the
addresses correctly. When you say you can send a test email, are you using
the Mailer plugin in the global config, or the Extended Email Plugin
settings to do this?

On Thu, Jul 9, 2020, 17:57 Greg Yeomans <gyeom...@venuetize.com> wrote:

> Greetings,
>
> We have been attempting to use the Email Extension plugin to send build
> reports to our developers but have yet to get a successful email out of the
> system.  I have the plugin setup with the same settings as the default mail
> plugin and tests with it work fine as I received test emails.  I have
> attached a screen shot if the resulting console output from my last attempt
> to test the issue.  We are currently using Jenkins v2.222.1 with the latest
> version of the plugin.  I have tried for months, off and on among other
> forest fires, to get this to work, but decided its time to look for more
> assistance.  I have TLS enabled with java/tomcat. Test emails through the
> original component work sending to port 25 but not 587 tests with the
> plugin fail with both ports.
>
> If you have any questions that could help me resolve the issue please let
> me know.
> --
>
> Greg Yeomans
> Senior Linux Administrator
> [image: Venuetize Logo]
> Venues. Monetized.
> M: +1.813.719.5757 | gyeom...@venuetize.com
> www.venuetize.com
>
> *"Venuetize makes the way people experience spaces easier, more personal,
> and enjoyable."*
>
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