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I just noticed that the outputted code has opening and closing enclosure tags:
<enclosure><enclosure url="https://mysite.com/sites/all/files/imagecache/story_images/images/image/20131007/file.jpg" length="1234" type="image/jpeg" /></enclosure>
When I try to validate the feed, it won't pass because it has opening and closing tags. Is this right?