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On this official Google page about canonical links it says:

Can rel="canonical" be a redirect?

Yes, you can specify a URL that redirects as a canonical URL. Google will then process the redirect as usual and try to index it.

There is no mention that this might dilute the impact of the canonical link. However, Google has made clear elsewhere that 301 redirects do dilute PageRank - roughly as much as a link dilutes PageRank. Is that relevant here? I'm assuming the answer is "no" but I wanted to confirm.

Relevant but not duplicate: Does Rel=Canonical Pass PR from Links or Just Fix Dup Content.

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As far as I know, you'll be fine, however, it doesn't make sense that the canonical (read "perfect") URI would be an "invalid" (redirecting) URI. If anything, it should be the opposite, any URI that is slightly invalid (and might generate a redirect) should have the rel="canonical" to indicate the correct (no redirect) path.

As an example, if you have a page under /foo/blah but your system forces a slash at the end of all paths, then you'd redirect to /foo/blah/ and that should be the canonical.

Now, you could write a system where /foo/blah does not redirect, instead you simply tell users and robots that the proper path is /foo/blah/ using the rel="canonical" link. That's where canonical is actually useful. That way Google can register /foo/blah as an equivalent of /foo/blah/ and also not mark those two pages as duplicates.

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Thanks for the input. I totally agree that this isn't ideal and isn't really the spirit of canonical links. However, the context of this question is an enormous/complicated enterprise news website where tasks need to be prioritized. In our case fixing the canonical URLs to point to the correct, non-redirecting URLs would be a pain in the ass, so I wanted to know if the redirect would produce a penalty. If it doesn't, changing it isn't going to be a very high priority. –  tobek Nov 6 '13 at 22:07
    
In a redirect, what Google looks at is the number of hops. If you have 1 redirect, you're good, if you have more than 3, you're definitively spam. If you have 2 and 3, they may give you a little penalty. That's what I know of redirects. –  Alexis Wilke Nov 6 '13 at 22:11
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