Approved for public release, distribution is unlimited / An analysis of in-situ aircraft observations collected in the parent cloud of a waterspout is presented. Previous waterspout studies were confined mainly to photometric and model simulated data, no in-situ observations were made internal to the parent cloud. On 27 June 2002 the Cooperative Institute for Remotely Piloted Aircraft Studies (CIRPAS) UV-18A Twin Otter aircraft collected observations in a cloud that had developed in a cloud line, located approximately 15km south of Key West, and that formed a waterspout. This study attempts to analyze the waterspout formation process using these data and through a series of scale interactions, from the synoptic scale down to the individual cloud scale. Based upon the analyzed data a hypothetical formation process is developed. The background synoptic scale flow is shown to establish the necessary ambient shear as a key factor in the waterspout formation. The orientation of mesoscale convergent boundaries and thermodynamic processes, internal to the cloud, proved to be an essential factor in developing the vertical motion patterns necessary for formation of an organized circulation in the shear region and to provide the tipping and stretching of the resultant vortex necessary to account for the waterspout formation. This is consistent with conclusions derived from previous studies. / Captain, United States Air Force