Would this be considered cloaking and would it be a bad move?
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I posted this topic last night, http://moz.com/community/q/seo-dealing-with-a-cdn-on-a-site about issues I am having with a client's images falling out of index because they have a CDN now.
So I have come up with a work around, but it might be considered cloaking and I am not sure. A month ago we changed over to using a CDN and the images started falling out of the index after that. Currently when you land on a page the images are served from cdn.site.com What I am thinking about doing is detecting Google Bot and when Google Bot crawls the site serve images from site.com. The images will be the exact same images as served from the CDN so it is not a content switcharoo thing. It is just to try to get the images back in the index.
So would this be considered cloaking in your opinion?
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Cloaking no. What you would be doing is trying to help Google understand the images.
I feel this would be similar to detecting a language or IP and serving an image with text correctly translated. The purpose isn't malice in fact quite the opposite.
I have been leery of CDN's for any other purpose then delivering script for exactly the reason your client is in. When you think about it you can have 2 to 200 urls delivering the same images. Every time a bot crawls the site it sees X image is from a new location. How is the crawler suppose to understand what is actually there?
Anyway my thoughts, hope it helps.
Don