Welcome Corganis! :pary:
Do you get a message "picture uploaded" after pressing upload? Or another message? If it says "must be .Gif" or something similar, but you know it is .gif, then the error most likely is that you have upper case letters. It has to be *.gif, not Gif or GIF.
If you still have problems you can send the pic to Amarië or Rednell (Amarie@shiremail.com or Rednell@Planet-Tolkien.com) Very helpful girls! :) You could also send it to me (email@example.com), cause I'm really bored right now and could do with the distraction. :) Don't know if I'm able to help though! Hehe! :P:
What are you looking down here for?