For some reason Skype on the Mac won't let you run multiple accounts or sessions. To run multiple Skype sessions/accounts at the same time: * Create a new non-administrative user (making it the same name as the Skype account might make remembering what it's for off in the future easier) * Switch desktops or login as the new user and run Skype * Set the Skype password and select the option to "Sign me in when Skype starts" * Logoff and log back in as your normal user account on the mac * Open Terminal * Run ''su - [skype_user] -c /Applications/Skype.app/Contents/MacOS/Skype'' where ''[skype_user]'' is the new account you created on the mac * Enter the password for the [skype_user] account The only oddity I've noticed is that the dock status for the second Skype instance will constantly show a status of "Application Not Responding" despite the fact that all functionality is available from the top menus.