This weekend, I finally upgraded our Production instance of Atlassian JIRA to the latest release 5.2.11. It has been a long time coming really. I mean, we were still running 4.2 which I installed back in November 2010. I had been planning to upgrade JIRA at the end of 2011, but because of the complexity of doing a Manual Upgrade along with not having enough time to dedicate to the entire process, it kept getting delayed. Over the last month and a bit I had managed to do a test upgrade and migration to a new Windows Server 2012 server. It went smoothly and so I scheduled the upgrade of the Production environment.
The upgrade went mostly smoothly. I did get an error after the data import which was a bit daunting, but after restarting the JIRA service and reading through the logs it looked like it completed successfully and clicking around there didn’t seem to be anything wrong or missing. To make the migration even more challenging, I introduced proxying the JIRA instance through IIS using Application Request Routing. This is something I hadn’t used yet, but will probably play with some more. I also added changing the URL from http://server/jira to http://jira.domain.name, so there was redirect rules required. To top it all off, I also decided to migrate our existing Confluence across to the same new server as JIRA along with using the IIS proxying with ARR and make the same URL changes as JIRA.
The next step… start planning to upgrade our production Confluence instance to the latest release… have to upgrade to Version 4 first and then up to 5. Fun times ahead 🙂
Until next time!
CTRL F5.me 
Today was the first day back in the office with a full team using the latest and newest version of JIRA. It went relatively smoothly. There was a major issue in that some of the filters we had were not up to date with the most current data, but a re-index of the data resolved this. We also had a couple of users complain about the new “Autowatch” feature, however I managed to find out how to turn this off. It is basically in the profile settings page, you can either set it to Enabled or Disabled, or you can leave it as Inherit from the Global Settings.
Apart from these few issues, it was a relatively smooth upgrade. Now it would be great to work out how to get my Velocity Email Templates working!