At the moment, it is not allowed to drag and drop multiple issues at one time if the destination column is mapped to workflow status with a transition screen configured. This requires users to drag and drop issues one at a time.

To replicate :

• Configure the Done status to have a transition screen in the workflow.
• Map the Done status to a Board column
• Try drag and drop multiple issues at one time to that board

Result :

Message : Unable to transition multiple issues to Done. The transition screen is not supported when transitioning multiple issues.

It would be useful to allow this feature for cases where a bulk update of issues is needed on Software boards.