Xbox – Wireless Headset with Wired Controller

I today purchased two Xbox 360 Wireless Headsets (black, if you must know) for each controller that I have: one is Wired, the other is Wireless.

I went to go sync them with my Xbox and the first one went great. I was able to select the Ring of Light my Wireless controller was on and I could speak and hear normally.

The wired controller, however, was different. Completely following the instructions word-for-word, I signed in and everything. I turned on the Wireless Headset and tried to select Quadrant 2, however the headset would skip over that quadrant as if the wired controller already had a headset connected to it.

Has anyone else had this problem mixing and matching a wired controller with a wireless headset? According to many message boards I've read on this topic, this should be possible.

EDIT I've tried all the suggested troubleshooting steps and still nothing.

EDIT2 I've tried to connect the headset first, but once I try to connect the Wired controller, it knocks the headset off that Ring of Light until you hit the Connect button on the headset again, whereby it'll just default to 3rd and 4th quadrants (skipping over 1st and 2nd).

EDIT3 Any other suggestions out there?