Legistar is not currently designed to support recurring agenda items. There is, however, a workaround for this issue.
Resolution
The workaround for recurring agenda items is to use just one Legislative File and add each monthly report as a separate attachment. This will allow each discussion of the report to be its own history line and each month to have its own attachment. It’s a matter of setting actions to have the same file come back to the same spot and then changing the agenda date.
Set up a file type or use an existing file type.
Set up an action that doesn’t change the status and is not Final (e.g., something like Discussed).
Take that action on the recurring item in your Minutes screen.
After the meeting, go to the Minutes tab and double-click on the recurring item.
Change the Agenda Date to the new meeting date and click Go Back.
Repeat steps 4 & 5 as needed for each new instance.
The item will then appear on the next meeting in the same spot.
Note: One other thing that will change is that you will have to remember to uncheck Print this Attachment on Reports on the previous month’s attachment every time you are adding new months. That is less work than creating a whole new file for every report.