[1] 1992. I was extremely young, so I can't recall anything other than the location. In my adulthood, I can lookup the exact GPS coordinates. For privacy reasons, I'll say "Downeast Maine". It was about 1.5 hrs after sunset and I wasn't in bed, but it was dark, so I'd like to guess either the spring or fall - neither winter nor summer. I was old enough to know that you should note the change in perceived speed. It's note-worthy that Downeast Maine was not terribly far from Loring Airforce Base, which was still operating in those days.
[2] March 2018, at approximately 8:30-9pm. Again, I don't recall the exact date or time, (I should have written it down immediately), but we were outside Borrego Springs, California approximately 100 miles east of San Diego. San Diego is also very close to a lot of Military bases.
If it was just AFTER sunset you get a situation where the sun is set for you but it is NOT set for the satellite tens of miles above, as long as they're in the right part of the sky.
So one moves into the shadow of the earth, the other moves out - at a 90° angle.
[2] March 2018, at approximately 8:30-9pm. Again, I don't recall the exact date or time, (I should have written it down immediately), but we were outside Borrego Springs, California approximately 100 miles east of San Diego. San Diego is also very close to a lot of Military bases.