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I'm trying to outline text in illustrator or photoshop. How can you outline the text more than once? I can only get it to outline once?
 

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What you need to do is put an outline on the text, then copy and paste in place (ctrl +f), then make a larger outline around that copy and move it to the very back. You'll see the larger outline around the one on top.

Or you could create an outline, then create the outline to a shape, move it behind the text (now the old outline is a separate shape behind the text) then put another smaller outline around the text.
 
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