Outlook 2007 has a lot of calendar printing bugs, which I suppose, is why they released a Calendar Printing Assistant. Some were fixed in SP1. Others are just coming to my attention, probably because I don't print calendars.
The newest bug involves printing a series of full month calendars. If you start the series in a month that spans 6 calendar weeks, each monthly calendar contains 6 rows and the names of the months at the top of the print out will be screwy: "Dec", then "Dec – Feb", "Jan – Mar" etc.
When you begin printing the calendar in a month that spans 5 weeks every month will span 5 weeks and drop the last couple of days if they extend into the 6th week. At least the months are labeled correctly: Jan, Feb, March; too bad they're short a day or two.
The Calendar printing assistant always uses 5 weeks and addresses the problem by "compressing" the days in the 6th week into the blocks of the 5th week. If you prefer to use Outlook's native printing capabilities, you'll need to print the longer months separately.
Bonus tip: the date selection fields in Outlook's print dialog accept date shortcuts. I.e., if you want to print 6 months of calendars, set the starting month (any date within the month, if you choose to print full months) and type 6mo in the ending date field. Unfortunately, the Calendar Printing assistant doesn't use shortcuts and you'll need to type or select the ending date.
For other tools that will print the months correctly in 5 or 6 rows, see Calendar Printing Tools
Older versions of Outlook correctly draw either 5 or 6 rows, as needed.
Published December 17, 2007. Last updated on January 3, 2012.