Yes it possible to have the Outlook TSP to run on a MS Terminal Server client but You must be logged on as the user you wish to use the functinality as.
Close Outlook and any other dialer programs until the very end of installation.
1. Clean install of Cisco TSP (remove any oldones and re-boot first).
2. Reboot
3. Configure the setup by using the Phone/modem options in control panel.
4. Reboot
5. Open up the MS phone dialer and select the Cisco phone you wish to use.
6. Dial a test call.