There are a couple of different things to do. We had consultants set ours up so I will look up how to do both.
The first thing that you are looking for, it appears, is to have the music on hold constantly keep going and not have it start over at the beginning with each time the caller is put on hold. This is definately possible and one of the necessary modifications we had done here. The other thing may be to place diffeent music on hold files out there (at least put a file out there with your own music) to make it more friendly.
Both of these are documented somewhere on Cisco from what I have heard, but the real world config may be better.
Service-->Media Resource --> Music on hold Audio Source
Select the stream that you are playing the check the box
Play continuously (repeat) then at the bottom of the page click the "Reset MOH Servers" button to make the change effective. After that anyone going into hold picks up the stream from where it is currently in the track.
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