You are going to have a hell of a time finding a dock that will work with your case. Unless utterbox is like SwitchEasy and includes the dock adapters that make it work WITH the case, you might be looking for a while.
That looks a little long to me, but I don't know how thick otterbox cases are. Seems like with that extender most docks would have the entire weight of the phone now supported by just the jack.
I don't think anything would go wrong with the phone itself since it's a female port. The worst thing I see happening is maybe stressing the dock port after some time.
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