Pictured is the current world record holder.
The Massif des Ecrins seen from the Pic de Finestrelles (2.820 m.) in the Pyrenees - A distance of 437 km(272 miles) by Marc Bret in 2016. Barre des Écrins (4.102 m) of the Dauphiné Alps is seen in the middle left of the image.

I assume at that range you would have to take into consideration any number of atmospheric distortion effects and the earth's curvature? What are the theoretical limits of photography?
I assume /sci/ can explain.
Image sourced from the photographer's site.
https://beyondrange.wordpress.com/2016/08/03/pic-de-finestrelles-pic-gaspard-ecrins-443-km/