Redirects Not Working For PDFs

I had this problem as well and found that you cannot have special URL characters in the URL to redirect.

If the file name has spaces such as
file name 2.pdf then enter it as such in the URL.
IE: https://my-site.com/downloads/file name 2.pdf.

Using https://my-site.com/downloads/file$20name%203.pdf will not work.

WordPress will actually change the name of a file upload to eliminate this problem in your media. WordPress adds a – in place of the space in the uploaded file if it detects a space. So check to make sure you have the actual file name stored in your media exactly as WordPress stored it so the pdf redirected to can be found (can cause 404’s if not the same).