Alright, as it turns out, my Authentication Plugin was conflicting with the redirection (I have now learned that it is a pretty common issue), so I managed to fix it by fiddling with the rules of my authentication plugin.
Notably, 404 error redirections have to be handled within the Authentication Plugin by checking the route using the "isDispatchable" method and "manually" changing the routes towards a specific 404 page.
Well at least that did it for me, but the important thing to know is that there is no single solution to Authentication Plugin conflicts because every authentication plugin is different, depending on the purpose of it.