OK, this was the key hint, "phone entry", until now I was not able to reproduce the same issue as you, because I dialed by typing or by redialing from last dials list.
Thanks for the reply, but the issue also occurs if redialing from the incoming calls list. Please have a look at that code as well.
Four more issues and I can stop bugging you

1) If the media service is running, everything breaks. When I stop the media service, the system appears to work correctly (mostly.) Starting the media service results in me hearing the windows error sound, with no pop up. Once the first call is made or received with this service running, I hear the same windows error sound one more time, and from that point forward, nothing works right until I stop that service.
2) None of the system extensions are registered, other than FAX. I am using a demo key for the 3CX PBX, which is supposed to unlock everything. This is a huge deterrent in convincing me to purchase the product. If I cannot test voicemail, call routing via the digital assistant, ring groups, API calls, etc., then I cannot buy this product.
3) Call quality is not good over the skype gateway. Calls start off fairly clear, but deteriorate quickly with lots of warbling and digital artifacts. I'm specifically referring to calls be handled by the skype gateway, not extension to extension calls.
4) Had an employee install the 3cx softphone offsite at his location. He called a couple of the extensions in the office and nobody was ever able to hear him. He verified his Windows 7 settings, and that the OS was receiving input from his microphone. We went over all the softphone configurations and preferences ensuring the appropriate input was specified, and turned up, and ports opened, etc. We never did get a softphone to softphone connecting working between him and anyone else, where we could hear him. Perhaps having the media service not running caused this?
Any assistance is appreciated. Thank you!