I put a bunch of new smilies in my board\smilies\default directory, i went to admin, smily admin, i went to the bottom and added all the new smiles and saved them they show up fine, typing in Http://boardurl/smileys/default/smileyname.gif works fine, yet if i go to edit a message it only shows the stock smileys ?
You have to go in and enable the smileys that you uploaded...
Admin -> Smileys and Smiley Sets -> Enable customised smileys
turned out to be a beta problem i had beta 4.1 .. installed rc1 and found that when i added all the smilies it made them hidden even though i had told it not to.