This will be my first time shipping a fig cutting. Will this fit into a small box along with couple of other cuttings wrapped? The cup is no wider than tweezers so I imagine that it will fit laying down. I wrapped this thing like a ancient artifact traveling from museum to museum, I didn't want any dirt spilling that might cause the roots to dry out. I also reinforced the part sticking out by wrapping the plastic around it adding a rubber band and scotch tape so that the cuttings won't shift ripping the one single root visible (the white line at the bottom of the cup).

Will this have to be shipped in a Small Flat-Rate Box or will it be consider Priority Mail if I tell them that they are plants as a gift and that i want them to arrive alive? Maybe I should keep one leaf on the other cuttings to convince them.

AFB,
its you that tells post office how to ship its your choice, flat rate shipping will take to long not good for plant.
Tell them priority mail 2 to 3 days.
I see its already to go , its a good idea to put on the top of soil in cup some damp paper or something similar then tape over it to hold it together.
Secure well to keep from bouncing around.
One pound and under is about 5.00 to ship priority mail over and i believe up to several pouonds is about 10.00, these are approximate numbers.
The faster plant arrives the better is my thinking as i have shipped priority mail and have not had any problems in past except once when i did not secure plant real well .