I would like to put PDF files from local to remote and have local files deleted once complete

I am uploading scanned files (PDF only) to a Local folder and need to send to remote SFTP... I have this working using a PUT but once files are uploaded and deleted the session ends... I would like the session to continue looking for files in the Local until the session is manually ended... One other note is the remote folder automatically ingest/deletes what it receives so I'm not sure keepuptodate or sync will work... Using WinSCP 5.9.4

Your can loop your script from a batch file, like shown for example here:
https://winscp.net/eng/docs/library_example_keep_local_directory_up_to_date#scripting