Gears Jira-enhancement-tools is not registered with the Atlassian Marketplace, so they cannot verify the compatibility with any version on marketplace and will have to test it after the upgrade
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Ideally you perform the upgrade on a test environment first and check whether everything works as expected before upgrading your production environment.
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Thank you for your question. As of Jira Service Management Data Center (JSM DC) version 4.15, the Insight Asset Management app has been bundled out of the box with the product.
Insight - Asset Management will still work with Jira Software Data Center under certain scenarios, however now that that now you have upgraded to a version higher than 8.14, I believe you’ll need a license for JSM DC to get access to Insight - Asset Management and Insight Discovery functionality. This can be a minimum tier license for JSM DC.
You're best off referring to the details underneath 'Will Insight - Asset Management and Insight Discovery work with Jira Software Data Center?' on our public FAQs, as it provides further information about the different factors and scenarios to consider.
I hope that helps,
Charlie
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Start with this documentation Upgrading Jira applications where you'll find an upgrade checklist, preparation steps and at the bottom of the page: procedures depenindg on your environment.
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