Do you have a Port Status Monitor trace that we could check? This seems configuration and perhaps an user is sending the call to another call handler and then pressing another number that sends it to the operator.
The trace will tell us what happened with the call.
You will find the tool at this link along with a video that will help you with the setup:
Not sure about this issue since the DTMFs are not getting to UC and it is an MGCP. the only thought that I have is that the failed calls are getting as G.729 and the DTMFs are sent inband with the voice, there is a chance that the DTMFs are lost after coding/decoding the voice.
Have you checked the codec that is used on the failed calls? Is it G.711 or G.7129?
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