Shoutbox

The script just replaces characters (a-z and A-Z) with others. This means that it changes the text (before the message is sent) to something different. This means the emoticon is no longer in the post. It's a common, known problem with scripts that replace characters. I think if you set emoticons to use symbols and numbers rather than letters it'll work.

Personally I think that there should be a "standard" naming convention for naming emoticons. This forum for example uses :name: for many emoticons. This would make it easier to check for emoticons in a message and leave that text as it is.