During the early post-launch phase of the Landsat 9 mission, the Landsat 8 and 9 mission teams conducted a successful under-fly of Landsat 8 by Landsat 9, allowing for the near-simultaneous data collection of common Earth targets by the on-board sensors for cross-calibration. This effort, coordinated by the Landsat Calibration and Validation team, required contributions from various entities across National Aeronautics and Space Administration and U.S. Geological Survey such as Flight Dynamics, Systems, Mission Planning, and Flight Operations teams, beginning about 18 months prior to launch. Plans existed to allow this under-fly for any possible launch date of Landsat 9. This included 16 ascent plans and 16 data acquisition plans, one for every day of the Landsat orbital repeat period, with a minimum of 5 days of useful coverage overlap between the sensors. After the Landsat 9 launch, the plan executed, and led to the acquisition of over 2000 partial to full overlapping scene pairs. Although containing less than the expected number of scenes, this dataset was larger than previous Landsat mission under-fly efforts and more than sufficient for performing cross-calibration of the Landsat 8 and Landsat 9 sensors. The details of the planning process and execution of this under-fly are presented.