Basic Question on bit setup

I should know the answer to this, but now I'm not sure.

When I setup a carve and the machine measures the board and then has me insert the bits, I have always just estimated about where the bit will be when I put in for the carve.

I have the old anti-vibration setup (can't remember the name of it) and I slide the bits into the sleeve and don't have stops, so I'm just estimating.

The question is, when I do the actual carve and the machine says that the depth of the bit doesn't match (from the original setup) I always just hit "continue."
Does the machine adjust to the depth of the bit I just installed or is it going to carve the depth based on the original setup?

Thanks!

Edit: That anti vibration vibration setup I was referring to is the Rock Chuck.

It will use the new bit measurement that it just saw...

Ok, thanks for the response. I can't figure out then why some carves that are identical setups carve deeper.

I use a rock chuck. I use a piece of masking tape (pin stripe width) once I have it set. I also have a plastic tube that the bit came in and have it cut to length and use that to keep the measurement the same. Both ways have always worked out for me.