Does anybody know if while on headset mode the keyset is able to announce pages over the speakerphone, instead of the headset. My customer service reps don't like to keep their headsets on all day and are unable to here if someone from shipping would page them.

Nope the headset mode throughs all speaker functions to the handset port while active.

Once you activate the headset mode on the phone, you are disabling the hookswitch.
Try changing to "Ring" on ICM to calls instead of "Auto Answer".

Take the phones out of headset mode and use a handsetlifter plantronics makes one that fits the samsung key sets nicely

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Altcomm @ A.S.E Inc