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When I use the file system to store items from the Media Library, I can see that each item stores either an absolute path or one that is relative from the webroot - not a path that is relative from the Media.FileFolder setting.

This means that I cannot use the same data in dev and live if they have a different Media.FileFolder (which they do).

Is there a way to configure Sitecore so that the path of every item in the Media Library is relative to the Media.FileFolder?

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You are able to configure virtual folder in IIS that will point to absolute location on your server, e.g.: "SharedMedia" folder that point to "C:\SharedMedia". Then you will be able to configure Sitecore use this virtual folder as location for media files:

<setting name="Media.UploadAsFiles" value="true">
<setting name="Media.FileFolder" value="/SharedMedia">

There are more detail how to do it in this article.

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