diff --git a/tests/run/errorhandling.check b/tests/run/errorhandling.check
new file mode 100644
index 000000000000..882ca57f5022
--- /dev/null
+++ b/tests/run/errorhandling.check
@@ -0,0 +1,4 @@
+breakTest
+optTest
+resultTest
+Person(Kostas,5)
diff --git a/tests/run/errorhandling/Result.scala b/tests/run/errorhandling/Result.scala
new file mode 100644
index 000000000000..23f42c8100ac
--- /dev/null
+++ b/tests/run/errorhandling/Result.scala
@@ -0,0 +1,70 @@
+package dotty.util
+import boundary.Label
+
+abstract class Result[+T, +E]
+case class Ok[+T](value: T)  extends Result[T, Nothing]
+case class Err[+E](value: E) extends Result[Nothing, E]
+
+object Result:
+  extension [T, E](r: Result[T, E])
+
+    /** `_.?` propagates Err to current Label */
+    transparent inline def ? (using Label[Err[E]]): T = r match
+      case r: Ok[_] => r.value
+      case err => break(err.asInstanceOf[Err[E]])
+
+    /** If this is an `Err`, map its value */
+    def mapErr[E1](f: E => E1): Result[T, E1] = r match
+      case err: Err[_] => Err(f(err.value))
+      case ok: Ok[_] => ok
+
+    /** Map Ok values, propagate Errs */
+    def map[U](f: T => U): Result[U, E] = r match
+      case Ok(x) => Ok(f(x))
+      case err: Err[_] => err
+
+    /** Flatmap Ok values, propagate Errs */
+    def flatMap[U](f: T => Result[U, E]): Result[U, E] = r match
+      case Ok(x) => f(x)
+      case err: Err[_] => err
+
+    /** Validate both `r` and `other`; return a pair of successes or a list of failures. */
+    def * [U](other: Result[U, E]): Result[(T, U), List[E]] = (r, other) match
+      case (Ok(x), Ok(y))     => Ok((x, y))
+      case (Ok(_), Err(e))    => Err(e :: Nil)
+      case (Err(e), Ok(_))    => Err(e :: Nil)
+      case (Err(e1), Err(e2)) => Err(e1 :: e2 :: Nil)
+
+    /** Validate both `r` and `other`; return a tuple of successes or a list of failures.
+     *  Unlike with `*`, the right hand side `other` must be a `Result` returning a `Tuple`,
+     *  and the left hand side is added to it. See `Result.empty` for a convenient
+     *  right unit of chains of `*:`s.
+     */
+    def *: [U <: Tuple](other: Result[U, List[E]]): Result[T *: U, List[E]] = (r, other) match
+      case (Ok(x), Ok(ys))     => Ok(x *: ys)
+      case (Ok(_), es: Err[?]) => es
+      case (Err(e), Ok(_))     => Err(e :: Nil)
+      case (Err(e), Err(es))   => Err(e :: es)
+
+  /** Simlar to `Try`: Convert exceptions raised by `body` to `Err`s.
+   *  In principle, `Try[T]` should be equivalent to `Result[T, Exception]`.
+   *  Note that we do not want to catch and reify all Throwables.
+   *   - severe JVM errors that make continuation impossible should not be reified.
+   *   - control throwables like `boundary.Break` should not be caught. We want
+   *     them to return from a `Result`.
+   *  (Generally, the focus on `Throwable` in Scala libraries is a mistake.
+   *   Use `Exception` instead, as it was meant to in Java.)
+   */
+  inline def apply[T](body: => T): Result[T, Exception] =
+    try Ok(body)
+    catch case ex: Exception => Err(ex)
+
+  /** Right unit for chains of `*:`s. Returns an `Ok` with an `EmotyTuple` value. */
+  def empty: Result[EmptyTuple, Nothing] = Ok(EmptyTuple)
+end Result
+
+/** A prompt for `_.?`. It establishes a boundary to which `_.?` returns */
+object respond:
+  transparent inline def apply[T, E](inline body: Label[Err[E]] ?=> T): Result[T, E] =
+    boundary(Ok(body))
+
diff --git a/tests/run/errorhandling/Test.scala b/tests/run/errorhandling/Test.scala
new file mode 100644
index 000000000000..ef74da885ddb
--- /dev/null
+++ b/tests/run/errorhandling/Test.scala
@@ -0,0 +1,78 @@
+import dotty.util.*
+
+/** boundary/break as a replacement for non-local returns */
+def indexOf[T](xs: List[T], elem: T): Int =
+  boundary:
+    for (x, i) <- xs.zipWithIndex do
+      if x == elem then break(i)
+    -1
+
+def breakTest() =
+  println("breakTest")
+  assert(indexOf(List(1, 2, 3), 2) == 1)
+  assert(indexOf(List(1, 2, 3), 0) == -1)
+
+/** traverse becomes trivial to write */
+def traverse[T](xs: List[Option[T]]): Option[List[T]] =
+  optional(xs.map(_.?))
+
+def optTest() =
+  println("optTest")
+  assert(traverse(List(Some(1), Some(2), Some(3))) == Some(List(1, 2, 3)))
+  assert(traverse(List(Some(1), None, Some(3))) == None)
+
+/** A check function returning a Result[Unit, _] */
+inline def check[E](p: Boolean, err: E): Result[Unit, E] =
+  if p then Ok(()) else Err(err)
+
+/** Another variant of a check function that returns directly to the given
+ *  label in case of error.
+ */
+inline def check_![E](p: Boolean, err: E)(using l: boundary.Label[Err[E]]): Unit =
+  if p then () else l.break(Err(err))
+
+/** Use `Result` to convert exceptions to `Err` values */
+def parseDouble(s: String): Result[Double, Exception] =
+  Result(s.toDouble)
+
+def parseDoubles(ss: List[String]): Result[List[Double], Exception] =
+  respond:
+    ss.map(parseDouble(_).?)
+
+/** Demonstrate combination of `check` and `.?`. */
+def trySqrt(x: Double) = // inferred: Result[Double, String]
+  respond:
+    check(x >= 0, s"cannot take sqrt of negative $x").?
+    math.sqrt(x)
+
+/** Instead of `check(...).?` one can also use `check_!(...)`.
+ *  Note use of `mapErr` to convert Exception errors to String errors.
+ */
+def sumRoots(xs: List[String]) = // inferred: Result[Double, String]
+  respond:
+    check_!(xs.nonEmpty, "list is empty")           // direct jump
+    val ys = parseDoubles(xs).mapErr(_.toString).?  // direct jump
+    ys.reduce((x, y) => x + trySqrt(y).?)           // need exception to propagate `Err`
+
+def resultTest() =
+  println("resultTest")
+  def assertFail(value: Any, s: String) = value match
+    case Err(msg: String) => assert(msg.contains(s))
+  assert(sumRoots(List("1", "4", "9")) == Ok(6))
+  assertFail(sumRoots(List("1", "-2", "4")), "cannot take sqrt of negative")
+  assertFail(sumRoots(List()), "list is empty")
+  assertFail(sumRoots(List("1", "3ab")), "NumberFormatException")
+  val xs = sumRoots(List("1", "-2", "4")) *: sumRoots(List()) *: sumRoots(List("1", "3ab")) *: Result.empty
+  xs match
+    case Err(msgs) => assert(msgs.length == 3)
+    case _ => assert(false)
+  val ys = sumRoots(List("1", "2", "4")) *: sumRoots(List("1")) *: sumRoots(List("2")) *: Result.empty
+  ys match
+    case Ok((a, b, c)) => // ok
+    case _ => assert(false)
+
+@main def Test =
+  breakTest()
+  optTest()
+  resultTest()
+  parseCsvIgnoreErrors()
\ No newline at end of file
diff --git a/tests/run/errorhandling/break.scala b/tests/run/errorhandling/break.scala
new file mode 100644
index 000000000000..604d5ba888f7
--- /dev/null
+++ b/tests/run/errorhandling/break.scala
@@ -0,0 +1,22 @@
+package dotty.util
+import scala.util.control.ControlThrowable
+
+object boundary:
+
+  class Break[T](val label: Label[T], val value: T) extends ControlThrowable
+
+  class Label[T] extends ControlThrowable:
+    transparent inline def break(value: T): Nothing = throw Break(this, value)
+
+  transparent inline def apply[T <: R, R](inline body: Label[T] ?=> R): R =
+    val local = Label[T]()
+    try body(using local)
+    catch case ex: Break[T] @unchecked =>
+      if ex.label eq local then ex.value
+      else throw ex
+
+end boundary
+
+object break:
+  transparent inline def apply[T](value: T)(using l: boundary.Label[T]): Nothing =
+    l.break(value)
diff --git a/tests/run/errorhandling/kostas.scala b/tests/run/errorhandling/kostas.scala
new file mode 100644
index 000000000000..ec32750f4bc4
--- /dev/null
+++ b/tests/run/errorhandling/kostas.scala
@@ -0,0 +1,35 @@
+package optionMockup:
+  import dotty.util.boundary
+  object optional:
+    transparent inline def apply[T](inline body: boundary.Label[None.type] ?=> T): Option[T] =
+      boundary(Some(body))
+
+  extension [T](r: Option[T])
+    transparent inline def ? (using label: boundary.Label[None.type]): T = r match
+      case Some(x) => x
+      case None => label.break(None)
+
+import optionMockup.*
+
+case class Person(name: String, age: Int)
+
+object PersonCsvParserIgnoreErrors:
+  def parse(csv: Seq[String]): Seq[Person] =
+    for
+      line <- csv
+      columns = line.split(",")
+      parsed <- parseColumns(columns)
+    yield
+      parsed
+
+  private def parseColumns(columns: Seq[String]): Option[Person] =
+    columns match
+      case Seq(name, age) => parsePerson(name, age)
+      case _              => None
+
+  private def parsePerson(name: String, age: String): Option[Person] =
+    optional:
+      Person(name, age.toIntOption.?)
+
+def parseCsvIgnoreErrors() =
+  println(PersonCsvParserIgnoreErrors.parse(Seq("Kostas,5", "George,invalid", "too,many,columns")).mkString("\n"))
\ No newline at end of file
diff --git a/tests/run/errorhandling/optional.scala b/tests/run/errorhandling/optional.scala
new file mode 100644
index 000000000000..5dee9cb21996
--- /dev/null
+++ b/tests/run/errorhandling/optional.scala
@@ -0,0 +1,20 @@
+package dotty.util
+import boundary.Label
+
+/** A mockup of scala.Option */
+abstract class Option[+T]
+case class Some[+T](x: T) extends Option[T]
+case object None extends Option[Nothing]
+
+object Option:
+  /** This extension should be added to the companion object of scala.Option */
+  extension [T](r: Option[T])
+    transparent inline def ? (using label: Label[None.type]): T = r match
+      case Some(x) => x
+      case None => label.break(None)
+
+/** A prompt for `Option`, which establishes a boundary which `_.?` on `Option` can return */
+object optional:
+  transparent inline def apply[T](inline body: Label[None.type] ?=> T): Option[T] =
+    boundary(Some(body))
+