Pluto occultation was captured by SOFIA jetliner in 2015

A flight path the Stratospheric Observatory for Infrared Astronomy (SOFIA) jetliner gave it the ability to capture data as "Pluto's shadow fell on Earth" in 2015, according to NASA. --
Pluto's wispy atmosphere may be surprisingly robust: https://www.space.com/pluto-atmosphere-hazy-resilient-nasa-sofia.html

Credit: NASA