User blog comment:FutureKnightX/I'm making a letter to Bushiroad/@comment-5777478-20140718212740

For the Dragobond, Bushiroad has a SIMILAR rulling. See the rulling between and
 * Chillax!
 * Gargantua Punisher!!

The check timing for 0 or less life comes after all current effects have been resolved. So if u have 1 life and get hit by 2 crit penetrate, your life would drop to -1 then back up to 1 due to dragobond.