Epidural analgesia involves injection of anesthetics into the epidural space, using a Touhy needle to proceed through the layers in the epidural region and a “loss of resistance” (LOR) syringe to sense the environment stiffness. One of the leading causes of the two most common complications of epidural analgesia - accidental dural puncture and failed epidural – is the anesthesiologist’s case experience. Robotic simulation is an appealing solution to help train novices in this task. Another benefit of it is the ability to record the kinematic information throughout the procedure. In this work, we used a haptic bimanual simulator to explore the effect LOR probing strategies had on procedure outcomes. Our results indicate that most participants probed more with the LOR syringe in successful trials, compared to unsuccessful trials. Furthermore, this result was more prominent in the three layers preceding the epidural space. Our findings can assist in creating better training protocols for epidural analgesia. Based on our findings, we expect that instructing anesthesia residents to use the LOR syringe more extensively and educating them to do so more when they are in proximity to the epidural space can help improve skill acquisition in this task. Future studies are needed to test this prediction and develop an optimal training approach.