Is it as simple as paying for an on-demand instance and uploading a database/xml dump?
As simple as that - probably not... But close.
Have a look at https://confluence.atlassian.com/display/ONDEMANDKB/Migrating+from+JIRA+Server+to+JIRA+Cloud
I'd recommend upgrading to 6.X prior
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The documentation does say you *need* to be on the latest downloadable Server version.
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Hi Bryan,
Since the OnDemand JIRA version is always one minor version ahead of the standalone client, you do need to be on the latest standalone version before migrating in order for it to work (same same way you need to be on the latest standalone version to do the reverse process). If you are planning on doing this on your production instance, beware that there is no process to downgrade JIRA, so make sure to backup all your data beforehand.
Cheers
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