Quality skylights are critical to having a leaky-proof dome shell. You shouldn’t be relying on silicone and black tar to seal your skylights. These sealants often have to be redone once or twice each year. The skylights below are using a wood top cap which either deteriorates (cracking, warping, splitting) or, if cedar or redwood, creates a compatibility problem with silicone sealants.
The Skylight below relies on silicone for its seal. There is no apparent way for this skylight trim to maintain pressure on the silicone seal. Eventually, the silicone will shrink, opening passages for water entry.