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So it's been not sure how long, but it's been more than a year I think. When you have a gradient map layer in Photoshop, Bridge generates the preview without applying the gradient map. I'm using the latest versions, v12 for Bridge.
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Same problem with another user here: https://community.adobe.com/t5/bridge-discussions/thumbnails-don-t-show-b-amp-w-previews/m-p/1282280...