I use Outlook 2000 with Windows 2K workstation and Call manager 3.3
First create a user with the Cisco call manager administrator and assign the correct phone to use to it. Don't forget password and pin code you give to the user
From this same CCM administration, you can donload the TSP Service menu Application / Install plugins, click on the Cisco Telephony Service Provider link. This will download the service and you have to install it on the client PC.
Go to Control pannel (in W2K : Contol pannel / Modems and phones / Advanced). Select CiscoTSP001.tsp and click on configure : write user name and password. Check to write the ip addresses of our call manager in the right place too.
Reboot the pc.
Go into Outlook, select a contact in the mailbox and click on the phone button in the tool bar. In the form that just oppened, click on the third buttons for "option" (I don't know the caption because my Outlook is in french) and in the last combo select the line corresponding to your phone (Cisco line : [SEP....]). Now you can click on the first button (Start call I presume) for dialing. With my Cisco 7940, it start dialing with hand free function activated, very fine. Don't close the form untill the call is finished or it wil hang up.
You have to check that all the phone numbers are correctly encoded (no slash, no dot ...).