MITZPE DANNY, West Bank — One night in the fall of 1998, a self-professed “outpost entrepreneur” brought three trailers to a rugged hilltop in the Israeli-occupied West Bank and established his first pirate settlement.

Dozens of youthful supporters came to cheer on the entrepreneur, Shimon Riklin, whose wife, newborn and toddler joined him a few days later. A second family also moved in. To their initial surprise, nobody from the military or government came to remove them. “After six months,” Mr. Riklin said in a recent interview, “I understood it was a done deal.”

They named their outpost Mitzpe Danny, after a British immigrant stabbed to death by a Palestinian at the settlement across the highway, and went on over the next few months to help establish Mitzpe Hagit and then Neve Erez a short drive away. “I jumped from hill to hill,” Mr. Riklin said.

Today, more than 40 Orthodox Jewish families live in Mitzpe Danny, one of a string of outposts on a strategic ridge with breathtaking views southwest to Jerusalem’s Mount of Olives and east all the way to Jordan. They are part of an expansive network of about 100 outposts established mostly over the past two decades without government authorization.