I guess it might be that the Mac is trying to reconnect to the device even when it's in DFU mode, and that is messing things up. You see the red LED on the Puck when it's in bootloader mode?
Do you ever see it change to the Blue LED light?
Espruino is a JavaScript interpreter for low-power Microcontrollers. This site is both a support community for Espruino and a place to share what you are working on.
Have you tried doing this: http://www.espruino.com/Puck.js#i-can-t-reconnect-to-my-puck-js-on-mac-os
I guess it might be that the Mac is trying to reconnect to the device even when it's in DFU mode, and that is messing things up. You see the red LED on the Puck when it's in bootloader mode?
Do you ever see it change to the Blue LED light?