Hello @Shane Glendinning
You can connect them, but it’s not a true, native two-way sync.
If you want your Jira work to show up in Trello, the built-in way to do that is through "Jira lists." However, that only pulls Jira items into Trello, and it’s a Premium feature so it won’t help if you're on a free Trello board.
If your goal is to have Trello cards automatically create Jira tasks, you're better off using Trello Automation Instead of looking for a right-click option, you can set up a rule where a specific Trello event (like moving a card to a certain list) triggers the creation of a Jira issue. That’s usually a much better fit for this workflow.
As for the timeout error when trying to create a Jira item, that sounds like a connection hang-up. I'd try re-authorizing the Jira power-up or testing it in an incognito window to make sure a browser extension isn't interfering with the login.
Basically, the connection exists, but it depends on which direction you want the data to move. For Trello-to-Jira, automation is the way to go.
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