If it makes you feel any better, it's not just hilton...had a fun experience at an SPG property recently with the boss wondering where the day's work was at about 10 PM. Why, it had been stuck in my outbox for 2 hours due to the daily connection dropout right during mid-send...lovely.
(Completely agree that this falls into the category of "problems I'm pretty sure I could have fixed in high school with two lines of code")