Once you are prepared to do transitional movements, follow the flow of gravity first, such as moving from plank to chaturanga smoothly and evenly. Avoid jerking or bouncing during the transition. Once you have accomplished this going along with gravity, you might consider retracing steps against gravity.
If transitioning with gravity hurts a joint, continue with a holding posture for longer periods or go back to joint preparation exercises as explained in the 4th Element. Only after a considerable time has passed, should we explore returning again to the step where the pain was originated.