We replace pdf files all the time with the latest months version to the same link

Board Agenda for example the link will be Jan2019 then Feb2019 and so on.

Well for some reason when I replace the June pdf with the july pdf it keeps trying to uplaod the June document that doesnt exist and then fails to upload any other changes made. i have removed the link, removed the file, and i have remade the file i have tried to manually delete and upload and the upload always tries to upload the old version. how do i get this file to no want to upload. i have even rebooted my machine to see if that would clear it. any ideas?