Missing cut areas on certain type and library images

Good day, On the Shapeoko 4 plus, using a 90 degree, 301 bit, in Carbide Create, I’ve had problems with certain text not cutting deep enough to make a mark.
Old English for example, the small lines between the letters that connect one side of the letter to the other side are not carving. So if i am making the letter “U” the two side lines are carving at the correct depth but the bottom line is not carving at all. All depths are set the same in the projects.
I have also found the same thing with some library images, specifically, the skull and cross bones wearing a hat and displaying pistols. Everything except the right side of the hat carved without problem at .125 inches in depth.
Troubleshooting attempts include:
I’ve tried different depths and this did not help. I also tried the 60 degree bit, again it did not help. The wood is not warped and is secured tightly to the machine table. The wood measures at a consistent depth. I’ve even zeroed with the bit .01 mm into the stock.
When previewing the image it :
A. does not show the line
B. shows the line very faint
Any help or guidance would be appreciated.

The V carve MAXIMUM depth is constrained by the max depth setting in the toolpath settings. Depths less than the maximum are determined by plunging the V-bit into the design until both sides of the cutter touch the design.

See the bottom of this thread: Wimpy Stars is it my math? - #12 by WillAdams

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If you’ll upload the .c2d file and a photo showing how the cut turned out we can look into this with you in greater detail.

How did you measure this? Measure it with the machine. When you set your Z zero, check it in multiple spots around the part to ensure the top surface is flat. Or surface the top before the V-carve.

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Here are the uploads and a picture.

fort peaceful2.c2d (372 KB)
marks ssign.c2d (1.3 MB)

I used calipers to measure the depth.