When you first use Skylook, or sometimes after you install a newer version of Skylook, Skype needs to ask you to allow access, for security purposes. However this can cause problems because Skype does not always ask in an obvious way, and sometimes not at all due to problems in Skype.
Skype 4.0 and later
Skype […]

Some Skype call recording add-ins are know to cause issues with Skylook call recording.
If you have a Skype call recording add-in other than Skylook installed, we suggest that you leave the add-in in place to start with.
If however you experience problems with Skylook call recording, it is likely to be due to the presence of […]

Sometimes, ActiveSync will prevent Outlook from closing down properly when you close the main Outlook window. This will prevent Skylook starting when you restart Outlook. If, after installing Skylook, Skylook fails to start when you restart Outlook, click here for information on how to get Skylook running.