You cannot do that with the automation functionality that comes with JIRA service desk.
This answer has some more discussions around potential work arounds.
I think you can do it with the Service Desk Automation. There is an event called SLA time remaining. You can make an automation rule which will send a email when the event fires. You can find more info here:
You are absolutely correct that there is the ability to "Alert" a user using automation rules when the SLA is going to be breached soon. I don't disagree. The issue is that you cannot alert a dynamic user such as the "assignee" or "reporter" of an issue. To perform something like this would require the use of a plugin.
I just passed 2 minutes. You can pass any time you want. Any action in Jira affects performance. To know for sure we need to do performance testing on automation and this solution. I did not do that. Moreover in Automation you can choose only 30min and 60min. I guess it means that there is also a load on the system. But we need to do performance testing to be sure.
Another option, if you have JIRA workflows plugin, is that it has a post function "send email". We use that quite a bit. Create a transition that all it does is that post function "send email". Then use automation when breaching to invoke that transition which just sends email. The Send email is very configurable.
We are currently using that to remind our approvers when it breaches time to approve.
Hope that helps...
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