I though you could set it up where Outlook would "push" calendar meetings from the OUtlook calendar to the new iCloud calendar it created, is that not true? It's not working for me....

I have Outlook set up with a work calendar; I was also able to successfully set up iCloud on my computer. When I intially set it up, it transferred all my Outlook meetings to a new iCloud calendar that I could view through Outlook or on my iPhone, woohoo! However, since that initial transfer, nothing has pushed to me iCloud calendar from my Outlook calendar. I was under the impression that once set up, iCloud would automatically push info to/from my Outlook calendar, but that doesn't seem to be happening...can anyone help?