Nearly 45 years after its construction, the efficiency of the vertical support heat pipes along the Trans-Alaska Pipeline System (TAPS) has shown signs of degradation. These heat pipes are crucial for maintaining ground stability in permafrost regions, where the pipeline is elevated for over half of its 800-mile length. Filled with liquid ammonia, the heat pipes transfer heat from the bottom to the top, preventing excessive thawing around the support structures. Ground-based monitoring of these pipes is time-consuming, lengthy, and costly. To address this, Alyeska Pipeline Service Company, the owner of TAPS, contracted NV5 to develop an aerial monitoring solution using high-resolution thermal infrared technology and image recognition. This innovative solution includes unique approaches throughout the workflow, starting with optimized low elevation helicopter flight patterns and timing, applying image recognition to identify the heat pipes, conducting automated analysis for each pipe, and reporting results in geospatial and digital formats. Our presentation brings to light the results we achieved in terms of workflow development, accuracy, scalability, and repeatability.