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A few more of my thoughts on the new Jetpack "Photon" feature.
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Tevya Washburn's profile photoMickey Mellen's profile photo
 
This looks/seems like a great idea. However, I'm personally concerned by the cached "forever" aspect. One reason is that on several sites that run eStores I'll use a thumbnail regeneration plugin to match the new sizes of image setting for the eStore and/or blog. If I understand correctly this will cache the various sizes for you. So I assume (thinking aloud here) that if those settings are changed, it'll adjust accordingly? But if you delete the image and upload a new version, it'll retain its filename and therefore not get updated by Photon. So you'd have to either 1. Keep all previous (unused) versions of all images on your site, or 2. rename the image before uploading. So I guess I'm not sure it'll be a problem... But I'm a little hesitant without some way to refresh the cached images. 
 
+Tevya Washburn Yes, you're correct about images named the same -- this won't update them.  For most uses, such as pages and posts and they're intending, that's not a problem.  In your case, it might be.

However, you can always generate new sizes of a given image.  Just add "w=123" for width, or "h=123" for height, etc.
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