Ok, this may be something really dumb, but I can't figure it out and it's getting pretty frustrating.
After having my Live subscription for about a year, I've decided to actually start playing games over Live (yeah, I know). Over the past couple of days, I've been playing Castle Crashers (had it since last year, just never really played it). Now, I'm having a ball and figured this would be a good time to use one of my two wireless headsets that I had sitting around.
After charging them, I'd hook one up and be ready to go. The problem is that, after about 10-15 minutes, it would shut off. When I would restart it, it would never hook back up to the controller, always opting for taking postition 2, 3, or 4. The only way I could get it to take position 1 again (which the controller is in) is by shutting off the controller, setting it to position 1, then turning the controller back on. After that happens, though, all four lights on the headset start blinking and I have nothing.
Help? If it's important, I'm using a wireless controller.
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You could be getting bad interference from something too.
Finally, not sure if you know or not, but if you hit the button you use to sync the wireless headset, just tap and release, it cycles through the different controller ports.
I have had quite a few problems with my headset, but nothing exactly like you, so just throwing stuff out there. Good luck!
And yeah, I know about cycling through the controller ports. That's what I meant by "position 1," etc. Sorry if that was unclear. But I can't get it to go back to port 1 after it disconnects.