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I have files where some of the graphics are larger than the document. Is it possible to use "generate" for a layer where some content is outside of the document view? (so I'll have a png/jpg that is larger than the document itself?) I presume 'no', but thought I might give it a shot here.

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No.

From Adobe's Help Docs on this topic:

Assets are clipped to the document boundaries. If an image does not fall within the document boundaries, Generator does not create the associated image assets.

I think that ties that one up with a bow.

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