Looks like the guys that put in the cable knew something that the conduit installer didn't!! The 90° connector installed like this is a violation of 300.18(A), Raceway Installation, Complete Run.
It could be the bending radius of the "stupid" (only my personal thoughts 'cause I hate 'em) 90° conn. would have wrecked the cable's integrity.
I've seen a lot of this blue sealtite installed in computer rooms. I don't believe it is listed for outdoor use (UV trouble) It still doesn't keep the water from coming in, though