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In a dynamically generated site (PHP, Python, pick your poison), 404 pages are normally handled dynamically to simply send a 404 header and display some error page on the URL that the user visited.

I'm wondering if a site has a large number of 404 pages and they for example, contain a significant number of links to help a visitor get to a useful part of the site, might a search engine see this as a cloaking of doorway pages?

I can't image search engines would generally punish you for having lots of 404s, you can't help people linking badly to you site but I can imaging they would punish you for cramming the 404 page with links.

As an extension of that. Is there any benefit of redirecting users to a single URL to display the 404 page, something like http://www.domain.com/404? How would this affect SEO?

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up vote 4 down vote accepted

You can do what you like with you 404 pages, as Google only retrieves the HTTP header, not the content.

No PageRank is assigned to the 404 page, or any of the links contained on/in it.

Redirecting to a 404 is merely adding an additional step in the chain (request -> 301/302 -> 404), so there's no value to be gained.

Putting links on your 404 pages, especially ones to pages that are relevant is always a good idea for your visitors.

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I'm curious as to whether there is any tangible evidence for the fact that a redirect to a 404 means as much as a direct 404 in terms of SEO effects. –  Grimace of Despair Oct 1 '12 at 12:32
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