The only issue I have with Toucan (or any program of this kind) is that files retain their filename when encrypted. This tells anyone looking at the files what sort of file it is, regardless of whether or not they can access it.
For the argument's sake, lets say I'm encrypting images or movie files not meant for anyone under 18. Getting a file back that's named "hardcore_a**l_s**ts.wmv.cpt" doesn't really hide anything. If these are personal files I don't want prying eyes to scope (like a boss or wife), just the filename can get you into trouble. I sound like a really sketchy guy. I'm terrible with scripting, but is there a way I can write one to rename all the files when encrypting?
This leaves another problem, however. How do I remember the original filenames and restore them upon decryption? This seems like an issue too large in scope to be handled by a script. Using randomly generated numbers and letters say 8 chars in length and saving them in an array that coincides with another array containing the original filenames and then writing this to a file in a way not readable by anything but the program seems like a solution, but I'm not much or a programmer.