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I've learned not to make assumptions, and didn't see this in the documentation, so two simple questions. My company is at version 2.2.4 and needs to get to 2.23.
1. Is everything backwards compatible?
2. Are upgrades are included in the price of subscription rather than an additional fee?
We're also upgrading JIRA from version 7.2.6 to 7.13 and all add-ons, including Portfolio at once. Any tips/warnings/lessons learned we should be aware of?
Upgrades can get pretty complicated so it is always a great Idea to double check everything prior to going live in production environments, and to touch on your last point first where you noted "Any tips/warnings/lessons learned we should be aware of?" I always stress that you should do a dry run and user acceptance testing in a staging system before going live with a production upgrade and have a backup ready to go to roll back on if conflicts arise.
The Best Resource we currently have on upgrades that offers up a deep dive into the recommended best practices including information on setting up a staging system for pre production upgrade, and details on add-on compatibility checks can be found here:
As portfolio Goes, with your current Jira Version upgrading from Portfolio 2.2.4 to the latest version 2.23.0 you should be good to go without issue with one click in the add-on manager, and the data compatibility would be a non issue unless your still have some Classic Plans, check out the Portfolio Migration Guide for details on migrating away from the portfolio classic plan structure if you still have any in use on the 2.2 version before upgrading.
but I say should because the base application may be able to accomplish this upgrade path without complications, there could be conflicts with other installed add-ons or customizations in the application and trigger buggy behavior causing the upgrade to fail on missing or contradictory modules applied to the system, this is rare but can occur so its always better to be safe than sorry.
For Upgrading add-ons the process I would recommend you follow is to Set up a staging server, make sure the the universal plugin manager (UPM) is upgraded to the latest version first then upgrade Add-ons. Once you can verify compatibility and that the new functionality is appropriate per user acceptance testing replicate on production.
Also with the note on functionality above, new features and changes to existing features are going to be introduced so its always recommended to run through the Release Notes for the product your upgrading, to take note of the changes and if there are any identified known issues listed that may be a blocker for your upgrade:
Thank you @Earl McCutcheon. We are putting everything into a lab first. We're upgrading JIRA, Confluence, Portfolio for Jira, ScriptRunner and any other add-ons at once. We're definitely reviewing all of the release notes and the upgrade Hub, but I just wanted to see if anyone had additional tips for me. Thank you for the detailed response!