I'm using the latest stable version on leopard and have the following problem:
i have two accounts (ICQ & MSN). I've generated OTR Keys for both account and set both account privacy to "Encrypt chats automatically". But this feature won't work. i have to set it per user. i noticed this while chatting with a friend who also uses the latest adium. After clicking on "initiate OTR encrypted chat", the encryption will be established.
edit: a notification would be nice, if the other side does also support OTR or not