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If I purchase a new licence for Confluence 4.0, would it be possible to upgrade from 2.9 directly to 4.0?
You'll want to move up through some of the point releases between 2.9 and 4.0
The Confluence 4 upgrade notes suggest that you upgrade to Confluence 3.5.x first. I would recommend reading all the release notes between 2.10 and 4.0.
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