Hi Anton,
Right now, the Trello Power-Up is only able to work with Cloud versions of Jira, and it's not possible to connect with Server versions, but I'll make sure the team knows you're looking for that!
You can, however, use the Unito Power-Up to connect Trello and many other services, including Jira Server: https://info.trello.com/power-ups/unito/jira
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