Successful tracking of a target from the High Altitude Balloon Experiment (HABE) requires selecting an initial position for the HABE platform so the greatest quantity and quality of imagery can be gathered for the longest duration. During the engagement period, a target typically covers a large distance while HABE drifts with the wind. The parameters of the engagement used to measure potential success depend directly on the capabilities of the tracking hardware and software. An engagement analysis technique has been developed which allows optimization of important engagement parameters. This technique can support a wide variety of tracking platforms which require pointing to specific locations or targets. Two methodologies are described in this paper which predict those positions for HABE where the most desirable engagements will be achieved against a nominal target. The desired objective is a long period of continuous maintainable track.