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If your license key is being rejected, most probably it's because you are trying to enter your key in the wrong place. See this page for more detailed information on providing a license key. Please remember that from version 2.1.0 TFS4JIRA accepts only Atlassian Marketplace licenses. If you have old license type, obtained directly from Spartez, please write to sales@spartezmarketing@spartez-software.com in order to have your license migrated.

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After you do that, you need to restart the application pool that TFS4JIRA synchronizer uses (the pool name is "TFS4JIRA Sync App Pool") - you can do that in the IIS Manager


Learn more about azure devops integration with Jira.