User have completed the transfer rule including an activity and approved the transfer rule. Afterward, the transfer rule became solid and was able to move the status of the workflow. It’s appear that the approval transfer rule get uncheck after moving the workflow to the next status.
This is exactly the way stat was designed to work. Keep in mind that Stat is focused on the CURRENT status and where to transfer that status next. So once you are at status 2, you can't see what was ready for the status transfer from 1 to 2, because it's no longer valid information for how to get from 2 to some other status.
The purpose of the popup window is to show the current user what needs to be done to get from the current status to the next status in the work flow. The window was not designed to show administrators what the user did to get to the current status. That is history and can be viewed by other means. For convenience, the popup window will allow the user to see how many times the CSR was transferred to the current status and what approvals were done to get it to that status. Below are the steps to view who approved the transfer rule: