You might have better luck in the Unified Communications forum, but here's something you can check into...
For that call handler, in the caller input options, make sure that it's set to "attempt transfer" to the call handler in question (the operator call handler, I presume). For that call handler in question, check to see which transfer rule is enabled. By default the "alternate" transfer rule is enabled and that rule will not actually transfer, but will go to the greeting instead.