In 2014 and 2015 there were triple shadow transits of Jupiter. The first one in June of 2014 had Jupiter very low and to the east, and it was mostly obscured with clouds. We had no success from the Carr Astronomical Observatory. The second was on a very cold night in January 2015. It was mostly overcast, but Jupiter was near the zenith and there was a sucker hole that stayed open for the duration of the transit. At one point I had to switch cameras because of a frozen battery.
Just after capturing the last frame the clouds closed in completely. Next one is in 2032.