The kipping handstand push-up (kHSPU) is an exercise performed by many thousands of CrossFit participants. The safety of kHSPUs has been questioned because of vertical impacts upon the head. Here, we measured the axial loads placed upon the head during kHSPUs and sought to identify other factors that may place participants at risk of injury. 16 volunteers from a single gym performed 3 sets of up to 7 kHSPUs with their head and one hand contacting force platforms. Forces were recorded continuously and video recording were made while performing the exercises. The force profiles showed distinct landing and kipping peaks. Participants landed with more force than during their normal headstand, but less than their body weight. The force on the head was greatest during the "kip," and was usually more than body weight. Participants who reported pain following kHSPUs moved their head into extension during the exercises. Forces to the head during kHSPUs were below forces proposed for damage to the young male cervical spine, but overlapped those proposed for female cervical spines. While kipping handstand push-ups may be safe for young and previously uninjured male athletes, they may be unsafe for females and for those with previous injury or other compromising factors.