Problems with Moodle sending emails

[Grommit]

Hi

 

I am getting this error .. any ideas ?

 

 

2020-08-06 15:16:07 Connection: opening to 52.98.18.18:587, timeout=300, options=array()

2020-08-06 15:16:07 Connection: opened

2020-08-06 15:16:07 SERVER -> CLIENT: 220 JN2P275CA0020.outlook.office365.com Microsoft ESMTP MAIL Service ready at Thu, 6 Aug 2020 15:18:57 +0000

2020-08-06 15:16:07 CLIENT -> SERVER: EHLO 192.168.2.40

2020-08-06 15:16:07 SERVER -> CLIENT: 250-JN2P275CA0020.outlook.office365.com Hello [41.21.194.54]

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-STARTTLS

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8

2020-08-06 15:16:07 CLIENT -> SERVER: STARTTLS

2020-08-06 15:16:07 SERVER -> CLIENT: 220 2.0.0 SMTP server ready

2020-08-06 15:16:07 Connection failed. Error #2: stream_socket_enable_crypto(): Peer certificate CN=`outlook.com' did not match expected CN=`52.98.18.18' [/var/www/html/moodle/lib/phpmailer/src/SMTP.php line 403]

2020-08-06 15:16:07 SMTP Error: Could not connect to SMTP host.

2020-08-06 15:16:07 CLIENT -> SERVER: QUIT

2020-08-06 15:16:07 SERVER -> CLIENT:

2020-08-06 15:16:07 SMTP ERROR: QUIT command failed:

2020-08-06 15:16:07 Connection: closed

[barnabythebear]

Hiya,

 

Have you installed the mail test plugin?

 

https://moodle.org/plugins/local_mailtest

 

Looks like a certificate issue maybe? Have you tried changing the smtp security settings to none to see if that allows mail?

 

Thanks,

 

Nigel.

[SimonHooker]

As barnabythebear mentioned it looks like a certificate issue in that the CN of the mailserver doesn't match the CN it's provided. The IP specified appears to be a Microsoft IP, so it's odd that it is returning an ip certificate instead of a properly named one. Might there be something intercepting the traffic + issuing its own certificate i.e. a firewall?

[Grommit]

Hi

 

It was working fine with Outlook.office365 SMTP until we changed it to "TLS" and authentication required

 

SMTP Host 52.98.18.18:587 or Outlook.office365.com

 

Still, doesn't work.. 8-/

[Grommit]

Thank you all... it was the DNS

[Katy]

Thank you all... it was the DNS

Another one for the rule, "it's always DNS, even when it doesn't look like DNS... it's DNS"