Evaluation keys are for the highest user tier available and are compatible across stand-alone product/add-on user tiers and license types.
You may like to refer to the page https://www.atlassian.com/licensing/purchase-licensing which provides most answers on licencing.
it will depend on how the plugin checks the number of users for compatibility. Some plugins complain (or simply fail to work) if the plugin licence is less than the JIRA base licence number.
Unfortunately it is not always obvious what has happened. If you are running on your own server it is worth checking the logs for any reported conflicts.
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