Notification emails are not sent

[Admin Recopart]

We have an installation of Jira and ServiceDesk and we've created a request through the web portal of ServiceDesk as a customer. Then an agent comments on this issue (request). 

I can see that the notification is triggered because we can see the outgoing mail in the outgoing mail queue. We've switched on logging and debug-logging for outgoing mail but nothing is shown regarding the customers email in the "atlassian-jira-outgoing-mail.log" file.

When the customer was created the email was sent successfully to the customer with invitation to create a password etc.

Also the notification helper says that this customer should get notification as long as the added comment is not done by him/her self. We've also checked that the customer has "notify me" enabled in profile settings.

What might be wrong?

[Admin Recopart]

We haven't checked the mail server (hard to do since it's Outlook 365?). But we do know that the settings are correct since other mails are sent correctly.

We've also checked the spam folders in the customer's mail.

I can't think of anything else to check.

[Jobin Kuruvilla [Adaptavist]]

Its hard to say as everything looks fine from the JIRA side. Did you investigate on the mail server? Is it actually sending the mail, after it is flushed from the JIRA queue? Since you are seeing the outgoing mail in the queue, I assume the settings are correct.

Can you also check on the customer end to see if the mail was marked as spam and was probably sent to a spam folder? Or rejected by the customer email server because of some rules?