Note: If you want to print an Overview map then please assure to provide a data frame named ‘overview’ in the ArcMap document used for publishing the ArcGIS Server Map Service configured as ArcGIS Server Map Service (for printing).
Set the desired Overview map extent in the ArcMap data frame properties of the ‘overview’ data frame.

‘overview’ dataframe with map extent to be used for Overview map in print output

'overview' dataframe in ArcMap layout view - dataframe size can be adjusted

Overview map in WebOffice 10 R3 print output - rotated print extent is displayed
For printing an overview map with dynamic printing (recommended) both functions have to be enabled in the project configuration. Using dynamic overview printing without dynamic printing will lead to a blank overview map on the print output.

Dynamic printing and dynamic overview map printing setup