using .2 and .3 probes for the first time

So, you have a tiny amount of exposed shoulder on a cylinder wall, presumably limited between an outer extent of the part and the pressed-in bearing's outer race?
I would be measuring a plane on the top surface of the bearing OD race,
leveling and origin to the Bearing's OD race plane,

-Doing this will eliminate the probe from dragging on the top surface of the bearing if it wasn't pressed-in perfectly square to whatever your current alignment is.-

Then construct my hits for the circle you're trying to measure with 1/2 the ruby diameter plus 0.001" or so for clearance (0.3mm ruby is 0.0118" diameter) divide by 2, you get ~0.006" then add one thousandth for clearance. Measure the circle at 0.007" above the bearing's OD race plane.
-If you've got more shoulder wall, bump it up 0.010" or more above the bearing plane.

If that doesn't work, you can add a thousandth at a time until it does.
-Or- If you run out of cylinder wall to move up (IE you are measuring a chamfer or are probing up the edge of the cylinder), you can play with your vector angle (instead of perfectly tangent to the cylinder, add 0.1 z vector away from bearing surface, so your prehit and retract are clearing the bearing with a tiny amount of z angle. Just know your measured diameter will have that amount of pythagorean's cosine error induced.

So, you have a tiny amount of exposed shoulder on a cylinder wall, presumably limited between an outer extent of the part and the pressed-in bearing's outer race?
I would be measuring a plane on the top surface of the bearing OD race,
leveling and origin to the Bearing's OD race plane,

-Doing this will eliminate the probe from dragging on the top surface of the bearing if it wasn't pressed-in perfectly square to whatever your current alignment is.-

Then construct my hits for the circle you're trying to measure with 1/2 the ruby diameter plus 0.001" or so for clearance (0.3mm ruby is 0.0118" diameter) divide by 2, you get ~0.006" then add one thousandth for clearance. Measure the circle at 0.007" above the bearing's OD race plane.
-If you've got more shoulder wall, bump it up 0.010" or more above the bearing plane.

If that doesn't work, you can add a thousandth at a time until it does.
-Or- If you run out of cylinder wall to move up (IE you are measuring a chamfer or are probing up the edge of the cylinder), you can play with your vector angle (instead of perfectly tangent to the cylinder, add 0.1 z vector away from bearing surface, so your prehit and retract are clearing the bearing with a tiny amount of z angle. Just know your measured diameter will have that amount of pythagorean's cosine error induced.