With the added weight of front and rear bumpers and winch my 2.5" teraflex lift sagged quite a bit. Is the gap between the bumpstop and lower plate to small and possibly that is the culprit for my harsh ride?

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The shock has limited compression. Gotta believe that is the major factor. If it is, and the tire has enough clearance in the wheel well, a set of ACOS from JKS is my prescription.

 

You still have room before the bumpstop itself actually hits. The jounce bumper is just like a shock absorber and not your actual bumpstop.

What shocks are you running ?

 

Bilstein 5100

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I would suggest a coil spacer to get you back to your original height. Then depending which shocks you have you might want to upgrade to something better. Last depending on how much lift you actually have you can improve your ride quality with some control arm brackets. They will get your control arms back to the factory angles. This will let the springs and shocks do their jobs better.