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Whenever you want to turn a smart object back into layers (without retaining transforms) it works fine until you check the "don't show again" box- then it'll never do it and will just act like clicking rasterize. To fix this, you'll have to reset all warning dialogs, which is extremely annoying. I've noticed this also happens whenever you add a keyboard shortcut to it.
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If I understand your problem correctly, it seems that everything functions properly on Windows, Ps version 26.8.0. Reverting smart objects with transforms back to layers and selecting "Do Not Show Again" does not impact anything; it is possible to create Smart Objects from layers back and forth without any issues.
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Could you explain the exact process you are talking about?
When I use Layer > Smart Objects > Convert to Layers on a transformed Smart Object I get this alert:
Adobe Photoshop 26.8.1 on Mac OS 14.6.1
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