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Hi Brad, As others have indicated, there's no reason a 301 redirect on a missing image shouldn't work - it's all based on the URL request (not the actual resource served, since the server intercepts the request and forwards it to another URL along with the 301 status code). I'd second Yaroslav's recommendation on a good WP plug-in for this (Redirection). You should be able to just use the URL string here to set the redirect where you want to point it. I would also suggest double-checking that these are actual links pointing to the image URL, not embeds of that image on these pages (some tools will pick that up as a link).  Finally, you may want to create a new page that includes a suitable replacement image if one is available, rather than redirecting to the replacement image file URL (bc this way the reclaimed PageRank will flow through to the rest of your site via your navigation). Best, Mike