Could you hear and talk to the external caller, when he is tranfered to a phone by the group?
(in this set-up, where IVM first takes the call and then tranfer it into the group with on-hold music)
I had similar problems, but also didn't hear the caller when he was transfered from a group to a phone (which is usually something, which I didn't prove during tests, I always thought, as long as the phone is ringing, connection will be ok).
It turns out, that the voip-provider didn't support transfer of calls correctly. That also explained in my case, why all worked well as long as all test were done with internal extensions.
I would suggest to try a different voip-provider only to test, if this could be the reason.
(By the way, I found it very interesting, that by sip-connections the external provider can influence, if a call is transferable or not...)
regards

Tjareson