diff --git a/jvm/src/test/scala/org/scalacheck/GenSpecification.scala b/jvm/src/test/scala/org/scalacheck/GenSpecification.scala
index 39dc92e0c..8290bd9b3 100644
--- a/jvm/src/test/scala/org/scalacheck/GenSpecification.scala
+++ b/jvm/src/test/scala/org/scalacheck/GenSpecification.scala
@@ -325,11 +325,37 @@ object GenSpecification extends Properties("Gen") {
 
   property("some") = forAll { n: Int =>
     forAll(some(n)) {
-      case Some(m) if m == n => true
+      case Some(m) => m == n
       case _ => false
     }
   }
 
+  property("tailRecM") = forAll { (init: Int, seeds: List[Seed]) =>
+    val g: ((Int, Int)) => Gen[Either[(Int, Int), Int]] =
+      {
+        case (c, x) if c <= 0 =>
+          Gen.const(Right(x))
+        case (c, x) =>
+          val g = Gen.choose(Int.MinValue, x)
+          g.map { i => Left(((c - 1), i)) }
+      }
+
+    val g1 = Gen.tailRecM((10, init))(g)
+    def g2(x: (Int, Int)): Gen[Int] = g(x).flatMap {
+      case Left(y) => g2(y)
+      case Right(x) => Gen.const(x)
+    }
+
+    val finalG2 = g2((10, init))
+
+
+    val params = Gen.Parameters.default
+
+    seeds.forall { seed =>
+      g1.pureApply(params, seed) == finalG2.pureApply(params, seed)
+    }
+  }
+
   property("uuid version 4") = forAll(uuid) { _.version == 4 }
 
   property("uuid unique") = forAll(uuid, uuid) {
diff --git a/src/main/scala/org/scalacheck/Gen.scala b/src/main/scala/org/scalacheck/Gen.scala
index 2afc0990b..a6c59d365 100644
--- a/src/main/scala/org/scalacheck/Gen.scala
+++ b/src/main/scala/org/scalacheck/Gen.scala
@@ -467,6 +467,40 @@ object Gen extends GenArities{
     g.map(b.fromIterable)
   }
 
+  /** Monadic recursion on Gen
+   * This is a stack-safe loop that is the same as:
+   *
+   * {{{
+   *
+   * fn(a).flatMap {
+   *   case Left(a) => tailRec(a)(fn)
+   *   case Right(b) => Gen.const(b)
+   *   }
+   *
+   * }}}
+   *
+   * which is useful for doing monadic loops without blowing up the
+   * stack
+   */
+  def tailRecM[A, B](a0: A)(fn: A => Gen[Either[A, B]]): Gen[B] = {
+    @tailrec
+    def tailRecMR(a: A, seed: Seed, labs: Set[String])(fn: (A, Seed) => R[Either[A, B]]): R[B] = {
+      val re = fn(a, seed)
+      val nextLabs = labs | re.labels
+      re.retrieve match {
+        case None => r(None, re.seed).copy(l = nextLabs)
+        case Some(Right(b)) => r(Some(b), re.seed).copy(l = nextLabs)
+        case Some(Left(a)) => tailRecMR(a, re.seed, nextLabs)(fn)
+      }
+    }
+
+    // This is the "Reader-style" appoach to making a stack-safe loop:
+    // we put one outer closure around an explicitly tailrec loop
+    gen[B] { (p: P, seed: Seed) =>
+      tailRecMR(a0, seed, Set.empty) { (a, seed) => fn(a).doApply(p, seed) }
+    }
+  }
+
   /** Wraps a generator lazily. The given parameter is only evaluated once,
    *  and not until the wrapper generator is evaluated. */
   def lzy[T](g: => Gen[T]): Gen[T] = {