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Linear closed scan

I'm trying to do a "Linear Closed Scan" on a pocket (see picture) and no matter how many "crossings" I put in the "Control Point" tab is always stops before it makes it around the entire pocket. I've also tried several "Linear Open Scan" and I still can't get my scans to go completely around. The print callout is for an all around profile so I was hoping to do it with one "Linear Closed Scan".