JSD offers the ability to set a Customer Notification when they submit an issue. It works when the issue is submitted through the Customer Portal, however, the same does not happen when submitting the issue through an issue collector.
We have tried setting a JIRA Automation rule to send an email on each issue tagged with the issue collector label, however it fails to deliver the email to the address the user submitted in the issue collector dialog, it only works if that address matches that of an user registered in JSD, which is not the most common use-case.
Is there any way to make JSD send an automated email notification to that email address?
JIRA can't send outbound notifications to just any email address. That email address has to actually be tied to a user account that exists in the database under the cwd_user table. I suspect this could have been a design choice to prevent people from trying to turn JIRA into a spam generating engine. But honestly, I'm not sure of the exact details.
I can understand why you might want to be able to send replies to these users without an account in JIRA yet, but right now there is not a means to do this in JIRA natively. Heck, you can't even share an issue in JIRA unless that user/email address is tied to an existing user account.
So in my view, the simpliest solution here would be to first request that these users sign up for your JIRA Service Desk instance. Since you can have an unlimited number of service desk customers, there is no problem in terms of licensing these additional accounts as JSD customers. As you noted, if the email address they enter in this form matches the email address on a user account, then yes, JIRA can send a notification to that user.
However, if that extra step of adding them as an account seems to be too much to do, it might be possible to do this with the use of a 3rd party plugin like Email Task. While I have not personally tried this plugin, I did find a comment on an old feature request that seems to indicate that this plugin might be able to provide this kind of functionality in JIRA.
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