Can't add-on an add-on

I am in the Manage Addons section of an on-premise JIRA via a browser on my workstation. I downloaded the Service Desk addon. I cannot add on the add-on. I get the spinner with "Uploading jira-servicedesk-2.0.2.obr... " but it stays stuck and never actually installs it.

Where can I go look for why the install is failing?

PS: I did have a previous version on at one time, but took it off due to the poor licensing model. Now that it makes a bit more sense, I'd like to try it again, but can't get it installed.

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I had a similar issue, until I figured out that the version of my JIRA was too old for version 2 of the service desk. After I updated JIRA to the most recent version (currently 6.3.7), I was able to install the plugin without any problems.

Yes, we found out it was the same issue. I was trying to upgrade SD then JIRA, but it has to be JIRA then SD.

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I'll add that I installed the "JIRA Syntax Highlighter Plugin" two days ago without any issue.

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