The article calls it “unlikely” but that feels almost unfair to the amount of planning they put in and the photographer’s past successes. It would be unlikely for me to pull it off, perhaps, but this sounds like the guy for the job.

I wonder if capturing the ISS is more difficult, moving at several kilometers per second, although the ISS trajectory can be accurately tracked and predicted with software, while a propeller airplane rising to around 11,000 feet has much more randomness to it, if you’re setting up your shot from the ground.