Ghosts in the Machine? Time Zone issues

Time Zone / Outlook calendar Issue.

My time zone EST. Computer EST, Sandy EST. When I create an appointment Sandy's webpage displays it at the correct time. However, when I update my Outlook calendar, I see it one hour earlier.

I had to adjust my settings at Sandy to reflect that my location is Chicago, instead of NYC. This allows it to place the items at the correct time, i.e. one hour ahead. Which is weird, because Chicago is 1 hour earlier than NYC. (Right?)