Sprint BB8530
os 5.0.0.654 official sprint

Hit speed dial letter > connected on screen > callee can hear me > I can NOT hear them > Hang up > redial with speed dial letter usually connects.

From what I can determine it is an OS issue.
or
how the number string is in the speed dial. eg () or dashes may be causing the problem.

Can anyone point me in the right direction?

I have exactly the same problem. For some unknown reason it does this more on one day than much less the next day. Sometime I notice I will speed dial a # and I can't hear any tones while it dials, and then I can't hear the other person. When I hang up and speed dial again and I can hear it, I can hear the other person. Very annoying.
Posted via BlackBerryForums.com Mobile

I have the same problem. I am on my third phone under warranty for this problem and every tech I've talked to hasn't heard of this issue. I'm beginning to think it's an OS issue too. Has anyone heard of this problem or of an upcoming or current fix?

It is an OS problem...I had the same issue with .654, now running .886 and problem is fixed. the newest .1030 also fixed the problem for me but was a laggy OS for my 8530 so I tried a few different versions and found 886 to be just what I needed/wanted.