A user had this question:
"When I restart Outlook after being Out of Office, the reminder doesn't come up to remind me to turn the Office Assistant off."
That is how it works in Outlook 2010 and up. Instead of a pop up, there is an Infobar under the ribbon. The Office Assistant button on the file tab will also show the out-of-office status.
The automatic Reply button in Backstage (File tab) is highlighted when Out-of-Office is enabled.
Configure Start and End Times
In Outlook 2010 and up, you can set a start and end time for Out-of-Office. This can be set ahead of time (such as first thing in the morning) and can turn itself off at the appointed time.
My Outlook 2010 shows no Start and End Times. I don't see a way to configure it. Once again, Microsoft has arbitrarily changed something that didn't need to be changed. It's as idiotic as moving the Show Desktop icon from the left to the right of the taskbar.
This is in the monthly view? It te calls aren't wide enough (because the window isn't wide enough), the times won't show.