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I know it's possible to setup a CDN with W3 Total Cache for cached content. However, how would I setup a CDN with WordPress to initially upload all media content (images, videos, files, etc.) directly to the CDN instead of my web host/local install. I'd like to completely bypass uploading content to my hosting account and simply host it via CDN.

For example: if I uploaded an image via WordPress, I'd like it to automatically be sent to the CDN.

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To totally bypass WP, just use the CDN native interface or a utility like cyberduck to upload you files directly to the CDN and embed the file from the "From URL" tab at the add media thing.

This can work with files and video but will be problematic with images as WP process images to create thumbnails and gather EXIF and location information if they have. If you need any of this then you can't totally bypass WP unless you are willing to generate this info by some other way.

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