Strange behavior from Picking Sheet Printing

I have a UDF(checkbox) on SO_Header called 'Additional Handling'.

When I open Picking Sheet Printing, and use the filters to say UDF_ADDITIONAL_HANDLING equal to "Y"....the correct orders print, but each pick sheet only has 1 line on it...even if the order has multiple lines.

If I change it to UDF_ADDITIONAL_HANDLING not equal to "N"...the pick sheets print out properly. 

Can anyone explain this? Or should I just accept that it works with not equal to?