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Licenses - Suppose we went for 250 and then changed our minds six months later and wanted to up it to 500... how much do we lose out?

JIRA + Agile and Confluence. If buy 250 and then before a year need to go to 500, how much money do we lose as the remaining part of the year we paid for is scrubbed? Thanks for info.

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Not much. It will override the existing maintenance period and will start a new one. See https://www.atlassian.com/licensing/jira#serverlicenses-4

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