Questions About "Missing Hole" Feature

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I am using an O-Inspect 322 with Calypso 6.6.1602 and I have some questions about the "Missing Hole" feature found under Resources>Features Setting Editor>Probing. I turned on "Missing Hole" on one particular feature because if the part is flipped in the fixture, then there is no longer a hole where it is supposed to be. I was running a part in which the hole location was slightly off, so the stylus glanced off of the edge but still went into the hole, but then it just sat there. There was no alarm triggered in the status window or any other indication that something was wrong. The stop light was still green and the stylus was just sitting in the middle of the hole. I put in a different part that had the correct hole location, but it would only run up until it got to that hole, then it would drive to the center of the hole (without contacting the edge) and just sit there. I had to completely close down the software, reload the program, and then the part would run every feature in the program. Does anyone have any experience with the "Missing Hole" feature, and does this behavior sound normal?