I'm upgrading from an old version, and here is a case where the amount of information is overwhelming. Right now my plan is to perform the following actions in our development environment:
1. Backup everything
2. Upgrade to 5.0
3. Upgrade to 5.1
4. Upgrade to 5.2
5. Upgrade to 5.11
6. Upgrade Greenhopper straight to latest version 6.2.1 from 5.7.4
Does anyone have a better idea or is this the way to go? Having to review/upgrade all the intermittent versions e.g. 5.1.1 would be exhausting.
You don't need to do this. You can go directly from 4.4.3 to 5.2.11.
Make sure you read all release notes and upgrade notes to understand the changes. Also, make sure the plugins, customizations are modified appropriately.
Just as a follow up, I was able to migrate easily from 4.4.3 to 6.0.1 by following the upgrade notes directly. I'm having problems with the SSO/Siteminder integration due to opensymphony not being supported from 5.0 onwards but that is a separate issue.
Make sure to check your admin project links as they might be broken, and we also found that IE 9 requires you to run in compatibility mode. We also found that we had never been connected to Atlassian directly in order to download plugins from the marketplace, where 6.0.1 makes it very clear as to whether you are connected or not. Still working on a few issues, but most of them are minor.
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