Do you mill de-husked barley

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Yes. Just like wheat, which is also huskless.

Unless you're milling way too tight it'll be fine. And unlike wheat, I seriously doubt you're using a high enough percentage to cause you any problems with a stuck grain bed.
 
Roast barley is indeed very brittle and will mostly turn into powder but, as already mentioned by another poster, the amount will be so small as to have no efffect on sparging. If you don't mill then I expect you will extract very little taste and color from it, in any case much less than any recipe calculator will predict.
 
You can try adding a bit of moisture first and letting the barley absorb some to soften it a bit. Give it 10 to 20 minutes before you mill. A spray would be better than a dump, mix it in so all of it gets just slightly damp.
 
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