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I want to non-destructively and non-bindingly use Free Transform such that the transformation is immediately reflected in multiple smart objects, as though each object were one "layer" of a common smart object. i.e., I want to use Free Transform one time, hit the checkmark, and see immediate changes across an arbitrary number of objects without needing to copy & replace contents.
How do I accomplish that?
A smart object can contain as many layers as you like. If you double click on your smart object in the layers panel it will open a new document tab for that smart object that you can add layers to and edit the same as you could any other document.
If you want to create a smart object with multiple layer simply select the layers you want in the layers panel, right click and select Convert to Smart Object. The resulting smart object you create will contain all the layers you selected. If you already have a number of smart objects, you can select those smart objects and convert those to another smart object. You will then have one main smart object with the other smart objects as layers within that main smart object (which you can then transform etc).
