Specifically we're looking to generate an email to a pager address whenever a VIP submits a an issue. We'd like to do this without using JEMH, because I don't know how well JEMH interacts with Service Desk's ability to create external "customers" automatically.
JIRA will have no way of flagging an issue created via email as a VIP issue. However if the user creates a ticket via the UI and this flag is set, then you can use a subscription filter which monitors recently created tickets.
Let's say I create a static JIRA User group that contains all of our VIP users. Is there any way to make the Service Desk set a VIP flag at that point, to which we could then subscribe?
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You could create a VIP only service desk to which access is granted based on this group, and then have a hidden custom field which is auto set to VIP which you can filter on. You can not have it automatically apply this to tickets. You may be able to work around it using the Automation plugin: https://marketplace.atlassian.com/plugins/com.atlassian.plugin.automation.jira-automation-plugin though I am not entirely sure.
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