When I add a UIStroke to an image without a background, it looks like this. NOTE: The ApplyStrokeMode is set to Contextual.

When I add a UIStroke to an image without a background, it looks like this. NOTE: The ApplyStrokeMode is set to Contextual.

That’s the intended effect, if you want to have a stroke on the image itself, you have to import it that way yourself.
No way roblox could do this
ui stroke will just add it around the image
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