I’m trying to get the headshot thumbnail of a dummy that I’ve made using a HumanoidDescription.
Example: 
I can use Players:GetUserThumbnailAsync to get the headshot thumbnail of any player, but I want to figure out how I could get one of these by using a HumanoidDescription. If it isn’t possible, how could I get the exact same angle used in ThumbnailType.HeadShot?
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If you don’t need the image to be changing, you could just take a photo of your NPC, and cut out the background. This would have the same effect for the most part, but you wouldn’t have to script it.
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It’s not possible to get that information from HumanoidDescription. I would recommend using viewports to achieve the same effect. You can read the announcement post here.
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Or check out the instructions under Model Thumbnails here: Toolbox | Documentation - Roblox Creator Hub