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Or in your favorite UNIX flavor:

export MEM_STICK=/Volumes/Data # Replace this with the path to your memory stick

mkdir $MEM_STICK/DCIM

cd /tmp

dd if=/dev/zero of=big.file block=1024 count=5242880

cat Y4Ixn.jpg big.file > $MEM_STICK/DCIM/big.file.jpg

True if you want to game the system - if you actually want to help them test out there service just upload 5gig of photos and video - I'm sure most people have that?

For me, I already have all my gigs of photos in DropBox, so I had to come up with a way outside of uploading all those images again. I unlocked the first 2GB or so with legit iphone images, but to get the rest of the space, used this method.

Does Dropbox compress files? I did this and it only updated the image itself in record time, yet it accounts to 5GB of space in the box.

You can use mkfile 5g testfile.jpg on OSX.