Order of cuts with multiple different cut depths

I’m trying to cut out train wheels for a toy train I am making. And since train wheels have a flange, what I did was set 3 co-centric circles.

Center circle is just bigger than the axle diameter (0.425x0.425), and is a pocket cut, no issue
Next circle is the majority of the wheel surface, cutting 3/8ths of 1/2 thick board (1.375x1.375)
Largest circle is 1/8th larger diameter than the previous (1.5x1.5), and is a 1/2" deep through cut, to cut out the wheel, leaving 1/16th ‘lip’ that is 1/8th thick around the wheel larger than the rest.

I would want the wheels cut in that order. And using the ‘send to front’/‘send to back’, if I send the through cut to the back, the axle pocket to the front, then what happens is it cuts the pocket, then the 3/8ths cut fine, then cuts only a single pass at the first depth step height around for the last circle, failing to cut the whole way through.

If I duplicate the workpiece to a new workpiece, delete the center two circles so I only have a through cut, and run that (keeping the machine zero and board in place), it makes an air cut where it first cut at depth, then makes the 2nd cut that completes cutting out the pieces.

This is also reflected with the cut estimate on the right panel, showing the 1>2>3 fails to cut through, but the 1>3>2 does, with the flange intact (although I highly doubt the pieces will be stable enough to survive the middle cut, about to test it though.)

Why does it fail to make the final depth pass with all 3 layered?

Onefinity machine, using Easel to exportt g-code, but I doubt that is the problem given Easel displays this error in the browser as well.
Cut settings: 1/4th downcut bit, 0.5" MDF, 40in/m feed, 24in/min plunge, 0.3in depth per pass, Offset fill, vertical plunge.
Changing the cut settings and bits around doesn’t show a different result in the estimate final cut on the right, so I don’t think this is going to be a bit or cut setting problem. It really feels like a calculation problem with the layering.

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