Currently, the process to bulk import a pdf file requires that each file have a unique file name. So in order to upload a transcript file for 200+ students, I have to save each pdf with a unique name, defeating the purpose of a bulk upload. The bulk upload workflow should be able to read the unique students IDs from the PDF file or allow me to use the same file name on the CSV file.
This is extremely important for us as well. We receive pdf files with transcripts and score reports every year for over 200 students. Our last program had no issue with this and we used it constantly!
I would create a bulk renaming script and rename the PDFs from a csv file. It's not hard. https://www.labnol.org/software/tutorials/rename-multiple-files-bulk-excel-googl-docs/2481/