I am upgrading from JIRA 4.0.1 to 6.4. My understanding is that I must first upgrade to 4.4.5, then to 6.4.
I am migrating to a new server as well, which simplifies things.
The documentation says that:
Is it possible to choose just one version of PostgreSQL to work with both JIRA 4.4.5 and 6.4? Of course the higher the PostgreSQL version, the better.
I could set up an intermediate server, install JIRA 4.4.5 and PostgreSQL 8.2, and just use it as a waystation.
After you upgrade Jira to 6.4, you might want to consider upgrading your Postgres database as well. It really depends on your internal environment. For example, if JIRA is the only subsystem using 8.4 and you have other subsystems using 9.X, then maybe upgrading JIRA to a 9.X release would eliminate 8.4 from your internal environment.
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