Thank you for the help. I can see my error was in the location I was measuring for the collar and endmill, along with how I was measuring the cup. The manual would be improved by showing the correct measuring points for both. I did see the notes regarding the photos, and do agree that creating a photo inside of the cup is probably really difficult.
I have now finished the installation, and it is correctly picking up and setting releasing the collets.
Thank you again for your help.