I was looking for an Outlook plugin for a long, long time and finally found a solution. Grab a copy of SIPTAPI here.
It's a freeware solution which will enable Outlook's "Call" feature. It works by creating a TAPI provider which will initiate a call to your SIP address and once you answer, it completes the call to the destination caller. Functionally, it's what Google Voice does for you when you have it dial. It calls you, you answer, and then a call is placed outbound to your destination. (Technically, it uses a SIP REFER.)
The big difference here is that the call is a 100% VoIP call just as if you had manually dialed it from your phone. It doesn't care if your using an ATA or softphone.
Further down on the SIPTAPI page there is a reference to Ian Sharpe's dial.exe. I installed that as well. It enables click-to-call for "tel:" URIs. It's a bit of a kludge but it does work!
..Marc..
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