The plus sign is what spaces get encoded to when a string such as a file name gets url encoded.
My guess is this legacy app actually had spaces in the file names, which most experienced web developers would not do. In fact we strip out spaces in urls entered by users in mojoportal (at least in url manager, not sure about 301 redirect manager).
I guess you might try going directly into the the database if the ui doesn't let you try using spaces instead of plus signs. I'm not sure that will solve it but it might.
Hope that helps,
Joe