Standard iPhone Headset functionality issue

I purchased the 3G iPhone when it first came out and have been very pleased. The standard headphones that came with the phone were great because I could stop and start music and pick up phone calls all with the click of a button.
Well now after 3 months of hardcore use the button broke. I called Apple Support up and they said it was no problem to replace it...just send them the old ones back...no questions asked. But now with the new pair...I find that the headset plug does not fit flush with the phone and I lost the playback functionality of the standard headset.
Is this a hardware issue or a software issue at this point? What should I do now?
(Sidebar: I have the most current iPhone software update as well as the most recent Leopard update and am religious when it comes to syncing and backing up the content of my iPhone)

Called apple back...they're gonna send me another replacement....they have the best support. They said if it turns out this new headset doesn't work then they can set up an appointment for me with an Apple Genius and look at my phone.

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