Just thumbing through the night sky as you do, and found what might be an interesting challenge.
It is a daylight challenge, albeit 6pm. So should be possible.
September 2nd, 6pm.
Jupiter, with Io, Ganymeade transiting, and Io's shaddow.
the window is only 30mins wide,
from 17:50 through to 18:20.
Or failing that the same again on 9th september, but at a later time of 20:00
Mac,