Hi Jonathon,
Sorry to hear that you are having problems with activating a licensing key for Jira server. I tried to lookup your account with some internal tools we have here, but I'm not seeing any Jira Server licenses on your account. I see a Confluence Server 10 user license on this account, but that is the only active license I see. Is it possible you have this Jira server license on another account (different email address)?
What sort of error are you seeing in Jira when trying to apply this license key? I am curious if perhaps the logging of Jira might also give us some more clues as to the problem here. You can find this log in the $JIRAHOME/log/atlassian-jira.log file on the server running Jira.
Your license will be for a specific Jira application such as Jira Core, Jira Software, or Jira Service Desk, but if you try to apply a Service Desk license to the Jira Software application, I would expect that the application would throw an error because it cannot accept this specific key. Alternatively, I have also seen some Jira Server setups where the database that Jira is trying to connect to might not have been setup correctly. If this happens Jira can't store the license key to the database and might show an error trying to activate the key when the source of the problem is actually the configuration of the database. If this happens, again the logs in Jira will tell us much more definitively than the web interface tends to do.
I would be interested to see this log myself. While our community site won't let you upload files directly, you could upload it to a service like google drive or dropbox and then generate a shared URL link where we could download it from. Please let me know, interested to see what we can learn from the logs here.
Andy
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