Looks like if you follow this process you can impact the order by adding the `opsbar-sequence` property values: https://community.atlassian.com/t5/Jira-questions/Changing-Order-of-the-Workflow-Transition-Buttons/qaq-p/239379

That said, it's very confusing and not well-documented, especially given this button/dropdown is the most prominent feature on Jira  

The ordering logic is not impacted at all by the order of statuses in the status settings screen.

Why???

The purpose of the ticket was to be able to reorder. How can we reorder statuses?

Hi everyone,

My name is Matt, I'm a product manager on the Jira Cloud team.

This issue has now been resolved by the honoring of the opsbar-sequence transition property in the new issue view (JRACLOUD-70702).

The approach we have taken will only affect the ordering of transitions within the new issue view. Nothing will change in the old issue view. The ordering logic is not impacted at all by the order of statuses in the status settings screen. The ordering logic is as follows:

• Always show transitions with the opsbar-sequence property first according to their opsbar-sequence value (lower values appear first)
• Then show remaining transitions ordered first by category (Todo, In Progress, Done)
• Within category order alphabetically by name of the status being transitioned to

Thank you all for your support and patience as we worked on this. Please don't be afraid to share any stories or workflow improvements that this allows so that they can be fed back to the team.

I This is simply lost functionality = a bug.  The workaround is time consuming and unnecessary: the data to implement the fix is currently embedded in the workflows.  Please make use of it.