i could not attach more than one file to an email message ( when i select for example 5 pictures and sent send by email i found that just one picture is attached )
by clicking on balckberry menu and choosing select options and then select the rest of images i want after that i click on the menu then send them via email and select medium size to send photos and finally i found that only on photo attached :(
By any chance is the photo that is attached the last one that you had selected? I am simply wondering if you have perhaps not really selected the multiple files -- merely thought that you had.