E-mail configuration with Office 365 SMTP details

I build and configure the Graylog server on Ubuntu 16.04 platform. Unfortunately, I do have a problem with configuring alert via e-mail. When I am doing test I do get an error:

The Graylog server encountered an error while trying to send an email. This is the detailed error message: org.apache.commons.mail.EmailException: Sending the email to the following server failed : smtp.office365.com:587 (javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587; nested exception is: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?)

Please, can you tell me how I can use Office 365 e-mail for alerting. I did use my organisation e-mail address: graylog@********.co.uk

you could have used the search in this forum, that would have revelead this:

Where you find a working solution.

Thank you for your reply. As a fact I did look through documentation and I did configure server.conf with office 365 smtp settings and my alert@*****.co.uk email. I can confirm that I can access from my server office 365 smtp service:

telnet smtp.office365.com 578

Connected to outlook-emeawest5.office365.com.

Unfortunately, I can’t run successfully connection test inside the Graylog GUI interface.

Help is much appreciated.

Best Regards

Sorry I did a typo port 587 is a port I did use inside my server.conf configuration.

your graylog server.log might reveal the issue. But the configuration that is needed is written down in the linked posting in this community. Including the pitfalls.

Shortly after I got an error, my server.log file shows as follows:

Does that indicate where is the problem buried?

Best Regards

Yes. Read the post I’ve linked to in my previous reply.

Hi Jochen

I see it now. Thank you very much. I did post it before I did read your last post ;). Anyway, once again thank you for your contribution.

Best Regards

Hi Jochen

All is working now. Once again thank you very much.

Best Regards

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