Dropped Drill Chuck

I recommend a step drill. Less prone to grabbing. It can drill large holes with less issues.
great for
thin material​
round stock​
tubing​
plastics​
brass / bronze​
 
If your chuck is separating with what you describe it is messed up.

Check for burrs or dents.

Paint the male side with marker and slide together.

Give a gentle twist and separate.

Should have even transfer, if just a few hint spots they are high.

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After you check it with the marker look at the JT real close for any nicks or dents in either mating surface. stone out any you find even if they look to small to matter.
When you assemble it make sure both surfaces are absolutely clean and free of and dust or oil or grease. Even the skin oil from touching it can reduce grip of the taper. I have never in my life had a chuck pop off the taper. I often use large S&D bits up to 2 inch in both AL and steel.
As mentioned lots of little steps is not the way to go. drill a pilot hole just big enough to clear the web of the final drill size and then dive in with the final drill. If the hole needs to be accurate then the final drill size should be about .015 small and bore or ream to final size.
 
Finally a chance to use the Prussian Blue sitting in the drawer for years! So I did that and it looks like there is a deformation you can sort of see in the chuck that spun into the arbor. If so, how does one knock that down? And do I stone the arbor?

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