Current tracking technologies used to estimate Soldier and weapon location and orientation are insufficient to support longrange direct fire engagements in live force-on-force exercises and mixed and augmented reality (AR) training applications. Tracking solutions developed for augmented reality only support engagements at ranges just over 50 meters, but Soldiers and Marines are trained to fire at targets at 375 meters or more. Laser-based systems suffer from a number of drawbacks: (1) they do not require shooters to lead moving targets, (2) they do not require soldiers to properly adjust weapon elevation based on target range, (3) they cannot represent grenade launchers, and (4) they are blocked by foliage. Each of these drawbacks results in negative training. We present a novel approach to determining hits and misses with small arms fire that enable longer-range engagements without the use of lasers for live, force-on-force training applications. The basic intuition to this novel approach is that instead of using high-resolution accuracy of soldier and weapon location (to within four centimeters) and orientation (to within 100 micro radians or better), the starting point for a calculation is the reported locations of the shooter and target and the shooter’s sight picture when the round is fired. No harnesses, markers, reflectors, or indicia are used in this approach. With a sight picture as the starting point of the computation we know the aim point with respect to the target precisely at the time the trigger is pulled. Was the shooter leading the target properly? Did the shooter aim above center of mass of the target because he was firing at long range? This information is used to compute whether a shooter should accurately get credit for a hit or miss at long range. The system, Optically-Based Small Arms Targeting (OBSAT) successfully demonstrated accurate recording of hits and misses at distances of up to 375 meters against stationary, moving, and partially occluded targets. Results of this work are presented as well as areas for future research required to make this technology fieldable.