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Upgrading Confluence and JIRA server after license expires

Our JIRA and Confluence server licenses are expiring soon and we would like to upgrade to the latest possible versions but do not plan on continuing maintenance for the next few years.  

Do we need to complete the upgrades prior to the license expiration? Or can we do the upgrade after the license has expired? (assuming we are upgrading to a version that was released prior to our license expiration date)

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Yes, you've understood it perfectly.

You can only upgrade a licenced Atlassian system to a version released before the end of your current licence.

Imagine your current licence ends today (1st October 2019).  If you upgrade next week, you can go to any version of the system that is currently download-able, because they came out before the end.  If Atlassian releases a new version tomorrow, you will not be able to use that version without getting a new licence.

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