Regex for pdf’s – Old .asp Site folder structure to new WordPress Media Folder(s)

Answering this here to save others time if they run into a similar issue.
Clarity on this issue provided in this answer on SO

Regular expression redirects only work when all the information about
the new location can be derived from the URL for the old location.
That isn’t the case here. You have new information in the new URLs.
The data that the document was uploaded is now in the URL when it
wasn’t before. There is no way to write a single rule with a regular
expression to redirect all the URLs.

You have a couple options:

  1. Redirect each PDF URL individually
  2. Upload your PDFs to your new site in their original locations

For my situation option #1 works best as follows (sample redirect using redirection plugin):

Source URL: /folder/sub-folder/sub-folder/somepdf.pdf
Target URL: /wp-content/uploads/2022/07/somepdf.pdf

Create a csv of the redirects and bulk upload.

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