I experienced this as well with Outlook 2013 and the new version CP5.1Desktop_05010206_full_x32. I found that the Call Pilot Extensions "Add-in" in Outlook 2013 was loading in the Inactive Application Add-ins section, messages would only play for about 3 - 5 seconds and then the player would quit. Changing the status of the CallPilot Extensions Add-in to Active by clicking the Go button at the bottom and adding a check to the box next to CallPilot Extensions solved the problem but only for that session. If I closed Outlook and re-launched, the problem returned. To resolve this I ended up noting the filename and path of the extension, going back to manage and removing the add-in, then click add and select the .DLL file again and the extension now properly loads with outlook every time. Hope that helps.
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