Hey everyone, I’m in a bit of a pickle and could use some advice. A company has asked me to help modernize their Jira (8.5.5) and Confluence (6.1.1) setups. They’re aiming for the latest long-term release of each.
The tricky part is that it’s all running on a Windows Server 2012 VM. I’m trying to figure out the smartest way to test this upgrade without messing things up.
I’m wondering if this plan makes sense:
- Set up a test server with Windows Server 2022
- Install SQL and copy over the existing database
- Install Jira 8.5.5 and Confluence 6.1.1 on the new server
- Connect to the copied database
- Use this setup to test the upgrade process
Does this sound doable? Am I missing something obvious? I feel like I might be overlooking some important details.
If anyone has gone through a similar upgrade process, I’d really appreciate your insights. What pitfalls should I watch out for? Any tips to make this go smoothly?
Thanks in advance for any help!
Your approach sounds solid, but there are a few things to consider. First, ensure you have a robust backup of the current system before attempting any changes. It’s crucial to test the upgrade path incrementally - don’t jump straight to the latest versions. Instead, upgrade to intermediate versions first, then to the latest LTS.
Also, check for any custom plugins or integrations. These can often cause issues during upgrades and may need updating or replacing. Pay attention to the database schema changes between versions and plan for potential downtime.
Lastly, document every step of the process. If something goes wrong, you’ll want a clear trail to backtrack. Good luck with the upgrade!
hey there! your plan sounds pretty good, but don’t forget to test the upgrade in stages. start with the next version after what you have, then move up step by step. also, watch out for custom stuff - plugins can be a real headache during upgrades. and definitley make backups before you do anything! good luck with the upgrade 
I’ve been through a similar upgrade process, and your plan is on the right track. One thing I’d strongly recommend is creating a complete snapshot of your production environment before starting. This saved me once when we hit an unexpected snag mid-upgrade.
Also, don’t underestimate the time needed for testing. We found issues with some custom workflows and reports that weren’t immediately apparent. Give yourself ample time to thoroughly test all critical functions post-upgrade.
Another tip: keep a detailed log of every step, including any errors or warnings you encounter. This became invaluable when we needed to troubleshoot later.
Lastly, consider the user impact. We scheduled our final upgrade over a weekend and had a small team ready to address any immediate issues users reported on Monday morning. This helped smooth the transition for our less tech-savvy colleagues.