Watch the Skies! A foul omen looms over the city of Riddleport. What could the dark blot over the city of swindlers and thieves mean? Apocalyptic whispers fill the street, priests search for signs from their gods, and rumours of strange happenings shake the city. Could this ominous portent be the work of a scheming crimeboss, mysterious cyphermages, or a petty pirate lord? Or does it prophesize some new menace come to Golarion? A step into Riddleport's high-stakes underworld of sin and debauchery reveals that not all in the pirate's paradise is as it seems. Only PCs can foil a terrible new plot that reaches from below to take fold of Varisia's city of sin. This volume of Pathfinder begins the Second Darkness Adventure Path, and includes:

• "Shadow in the Sky", an adventure for 1st-level characters, by Greg A. Vaughan.
• An exploration of Riddleport, home to gamblers, outcasts, pirates, and the seediest scoundrels in Varisia, by Greg A. Vaughan.
• A chance to make your fortunes at the Gold Goblin gambling hall and check out four new games from one of Riddleport's rowdiest gaming dens, by Mike Selinker, E. Jordan Bojar, Gwen Page, and Greg A. Vaughan.
• A new entry in the Pathfinder's Journal by jay Thompson. Eando Kline, deep within the roots of the orc city of Urgir, discovers that the gate to the Darklands is not unguarded.
• Four new monsters by Greg A. Vaughan. Cover art by Wayne Reynolds