We are running jira in a container on an Azure VM behind a reverse proxy. The jira VM does not have any public IP adress.
When sending a test email from jira, the email is successfully delivered, but marked as spam by our company's mailserver.
When sending a test email, we can see the following output
DEBUG SMTP: connected to host "abc-xy.mail.protection.outlook.com", port: 25
250-HEABCDEFGHIJK.mail.protection.outlook.com Hello [20.52.xx.yyy]
"abc-jira" is the name of the container, jira is running in. But we cannot find the associated IP adress 20.52.xx.yyy on any of our VMs. Thus, our question: when and how is this IP adress configured in jira? Does this happen during the installation process?
Thanks for your help!
"Jira while installing or while communicating to nodes does the java-based name resolution in that it calls Java API to get the IP on basis of hostname...so whatever the hostname resolves too is what it saves as the IP and also the IP address does not save anywhere in Jira."
In other words:
I would say that you should use the SMTP authenticated port like 587 or 465.
The reason the AntiSpam is marking the message as SPAM is that the message is sending without authentication.
I would recommend you follow this [https://confluence.atlassian.com/adminjiraserver/configuring-an-smtp-mail-server-to-send-notifications-947184044.html] KB to setup the right Outgoing Mail server on Jira.
Hope it helps
Dear @Artur Moura , thanks for your answer.
Our email Admin Team does not allow SMTPS, quoting Microsoft: Microsoft SMTPS statement
„SMTP AUTH doesn't support modern authentication (Modern Auth), and only uses basic authentication, so all you need to send email messages is a username and password. This makes SMTP AUTH a popular choice for attackers to send spam or phishing messages using compromised credentials. [...] Therefore, we highly recommend that you disable SMTP AUTH in your Exchange Online organization".
The instructions on setting up the Outgoing Mail server does not provide any information about the IP adress, jira uses for sending emails.
Given the fact this is a plain Jira server installation the reason why the instructions do not mention any outgoing IP mail addresses Jira uses is that this information is not known to Jira in that means.
Jira indeed sends out mails but it (more specifically the JVM under it) uses what is "there" - this will be the outgoing mail server you configure, like Artur already said.
I bet the IP 20.52...(...) which is unfortunately anonymized is part of Azure/Microsoft.
Which would be fine, as you said you host on Azure. Although your VM has a private IP - there will be a public one of some kind, which is needed to get mails out.
That being said I think you need to look closer on your mail infrastructure, not on Jira so much (basically this is also what Artur is saying, I am just repeating in some other words).
Sorry for the delay...
I also was in contact with our support. The following lines underline the above answers: "Jira while installing or while communicating to nodes does the java-based name resolution in that it calls Java API to get the IP on basis of hostname...so whatever the hostname resolves too is what it saves as the IP and also the IP address does not save anywhere in Jira."
This answere is very explicit and shows that we have to understand how Azure DNS works.
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