I have a 540 Whispering Slab(before masterworking it) with a Draw Time masterwork. But when I upgraded it, the masterwork was not applied. Because it was still 540 after masterworking it. So why didn't it get applied?!
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540 is the minimum draw time for bows. The only way you can utilize the masterwork is to change your bowstring to something else that would normally increase the draw time from there.