The Whole Heliosphere and Planetary Interactions initiative was established to leverage relatively quiet intervals during solar minimum to better understand the interconnectedness of the various domains in the heliosphere. This study provides an expansive mosaic of observations spanning from the Sun, through interplanetary space, to the magnetospheric response and subsequent effects on the ionosphere‐thermosphere‐mesosphere (ITM) system. To accomplish this, a diverse set of observational datasets are utilized from 2019 July 26 to October 16 (i.e., over three Carrington rotations, CR2220, CR2221, and CR2222) with connections of these observations to the more focused studies submitted to this special issue. Particularly, this study focuses on two long‐lived coronal holes and their varying impact in sculpting the heliosphere and driving of the magnetospheric system. As a result, the evolution of coronal holes, impacts on the inner heliosphere solar wind, glimpses at mesoscale solar wind variability, magnetospheric response to these evolving solar wind drivers, and resulting ITM phenomena are captured to reveal the interconnectedness of this system‐of‐systems.