Recently there was a bug involving the Boss fights in Italy. All the Bosses had ridiculously high health levels and were impossible to beat (1). The issue has been resolved but we are left with Bosses who have much higher health statistics than they did prior to the "fix". Most are still finding them impossible to beat because the Henchmen regenerate to 100% health when players get crushed or leave the fight to heal. After the fix was in place, a Zynga Official stated that "some of the henchman might still have goofy stats temporarily"(1). Right now the Henchmen are very difficult to beat so if this statement is true, expect it to get easier. Opening another window to heal in a different destination is not working at this time as well. According to the Zynga Customer Support page ITAL - 411, Factoids, and FAQ the Italian Boss fights are supposed to be challenging and are compared to the Beat the Feds Boss fights. Those who blew through Italy before all the changes found the Boss Fights to be laughable. When I fought them on my energy account, there weren't any challenges and I could kill some of them just by using a Grenade.
Post Italy Related Bugs Here, Boss fights at ruby level, impossible without "cheating"?, Italy Boss health....WTF????, but there haven't been any moderator replies for 2 days. Al Catraz, Super Moderator, stated on October 30th that a "fix was pushed recently for the Bosses" and if the issue with the henchmen persists to let him know. If everybody lets him know, he will be overwhelmed! This issue is definitely persisting away.
Some players have beat the Bosses but they have spent a lot of time attacking, getting crushed, travelling to a different destination, healing, traveling back to Italy, and repeating the process many times. A lot of stamina, clicks, time, and patience is needed. It's estimated that it takes about 30-45 minutes to defeat a Boss. I'm going to wait until more is known on what the permanent status of Boss Fights is going to be and the help option starts working the way it's suppose to.