iChat: Cannot Send a File Until After First Text is Sent

You cannot attach a file to a chat session until you have first sent text to the user.

Symptom

When you click the paper clip icon you hear a beep. The dialog box that normally appears for selecting the file does not appear.


Solution

Send a text message to the person you're chatting with before clicking the paper clip icon to send a file attachment.

Published Date: Feb 17, 2012