notification
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I am configuring to receive emails through pfsense using the email address smtp.office365.com.
but it is giving an error: Unable to send the message to support@connectsolution.com.br -- Error: Failed to connect to ssl://smtp.office365.com:465 [SMTP: Failed to connect socket: Operation timed out (code: -1, response:)]
Can someone help me?
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@vitor-connectsolution
I don't think, that smtp.office365.com is listening on port 465.
Try port 587 and uncheck "Secure SMTP Connection". -
Yep, they answer at 587
220 PR0P264CA0117.outlook.office365.com Microsoft ESMTP MAIL Service ready at Thu, 9 Nov 2023 15:51:14 +0000root@ns311465:~# openssl s_client -connect smtp.office365.com:465== looks like no one is at home .....
I've been questioning my favourite search bots a bit, and it really looks like Microsoft doesn't do "port 465" (native TLS SMTP mail or smtps)
They still support only "587" ? Rather bizarre.@vitor-connectsolution : microsoft.com really told you to use 465 ?
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There are several caveats to their 3 options. To simplify everything, if you have a static IP it's by far easiest to use "option 3" on that page and set up a connector that allows relaying by IP. One can control access out by firewall rules.
For "option 1" (username/password) you have to enable SMTP AUTH for your account or for your tenant, and use 587. In pfSense, despite the web page saying to set "TLS/StartTLS" to "enabled" you have to uncheck the TLS option and use 587 as @viragomann suggested.
"option 2" also is easy to set up but you can only send to your domain...however you can set up a distribution list to send to external addresses.
@Gertjan said in notification:
microsoft.com really told you to use 465
I think you misread, he said to use 587 not 465. :)Never mind I didn't realize you were responding to OP there.
