diff --git a/compiler/src/dotty/tools/dotc/transform/patmat/Space.scala b/compiler/src/dotty/tools/dotc/transform/patmat/Space.scala
index 708944434015..e5a69eb3335c 100644
--- a/compiler/src/dotty/tools/dotc/transform/patmat/Space.scala
+++ b/compiler/src/dotty/tools/dotc/transform/patmat/Space.scala
@@ -502,12 +502,13 @@ class SpaceEngine(using Context) extends SpaceLogic {
 
   /** Is `tp1` a subtype of `tp2`?  */
   def isSubType(tp1: Type, tp2: Type): Boolean = {
-    debug.println(TypeComparer.explained(_.isSubType(tp1, tp2)))
+    //debug.println(TypeComparer.explained(_.isSubType(tp1, tp2)))
     val res = if (ctx.explicitNulls) {
       tp1 <:< tp2
     } else {
       (tp1 != constantNullType || tp2 == constantNullType) && tp1 <:< tp2
     }
+    debug.println(i"$tp1 <:< $tp2 = $res")
     res
   }
 
@@ -663,7 +664,7 @@ class SpaceEngine(using Context) extends SpaceLogic {
         || cls.isAllOf(JavaEnumTrait)
         || tp.isRef(defn.BooleanClass)
         || tp.isRef(defn.UnitClass)
-    debug.println(s"decomposable: ${tp.show} = $res")
+    //debug.println(s"decomposable: ${tp.show} = $res")
     res
 
   /** Show friendly type name with current scope in mind
@@ -838,14 +839,26 @@ class SpaceEngine(using Context) extends SpaceLogic {
       }
     }.apply(false, tp)
 
+  /** Return the underlying type of non-module, non-constant, non-enum case singleton types.
+   *  Also widen ExprType to its result type.
+   *  For example, with `val opt = None`, widen `opt.type` to `None.type`. */
+  def toUnderlying(tp: Type)(using Context): Type = trace(i"toUnderlying($tp)", show = true)(tp match {
+    case _: ConstantType                            => tp
+    case tp: TermRef if tp.symbol.is(Module)        => tp
+    case tp: TermRef if tp.symbol.isAllOf(EnumCase) => tp
+    case tp: SingletonType                          => toUnderlying(tp.underlying)
+    case tp: ExprType                               => toUnderlying(tp.resultType)
+    case _                                          => tp
+  })
+
   def checkExhaustivity(_match: Match): Unit = {
     val Match(sel, cases) = _match
-    val selTyp = sel.tpe.widen.dealias
+    debug.println(i"checking exhaustivity of ${_match}")
 
     if (!exhaustivityCheckable(sel)) return
 
-    debug.println("checking " + _match.show)
-    debug.println("selTyp = " + selTyp.show)
+    val selTyp = toUnderlying(sel.tpe).dealias
+    debug.println(i"selTyp = $selTyp")
 
     val patternSpace = Or(cases.foldLeft(List.empty[Space]) { (acc, x) =>
       val space = if (x.guard.isEmpty) project(x.pat) else Empty
@@ -878,13 +891,14 @@ class SpaceEngine(using Context) extends SpaceLogic {
     && !sel.tpe.widen.isRef(defn.QuotedTypeClass)
 
   def checkRedundancy(_match: Match): Unit = {
-    debug.println(s"---------------checking redundant patterns ${_match.show}")
-
     val Match(sel, cases) = _match
-    val selTyp = sel.tpe.widen.dealias
+    debug.println(i"checking redundancy in $_match")
 
     if (!redundancyCheckable(sel)) return
 
+    val selTyp = toUnderlying(sel.tpe).dealias
+    debug.println(i"selTyp = $selTyp")
+
     val targetSpace =
       if !selTyp.classSymbol.isNullableClass then
         project(selTyp)
@@ -897,7 +911,7 @@ class SpaceEngine(using Context) extends SpaceLogic {
         if (x.guard.isEmpty) project(x.pat)
         else Empty
 
-      debug.println(s"${x.pat.show} ====> ${res}")
+      debug.println(s"${x.pat.show} ====> ${show(res)}")
       res
     }
 
@@ -912,7 +926,7 @@ class SpaceEngine(using Context) extends SpaceLogic {
         debug.println(s"prev: ${show(prevs)}")
 
         var covered = simplify(intersect(curr, targetSpace))
-        debug.println(s"covered: $covered")
+        debug.println(s"covered: ${show(covered)}")
 
         // `covered == Empty` may happen for primitive types with auto-conversion
         // see tests/patmat/reader.scala  tests/patmat/byte.scala
diff --git a/tests/patmat/i13342-testing.check b/tests/patmat/i13342-testing.check
new file mode 100644
index 000000000000..88418cde03a0
--- /dev/null
+++ b/tests/patmat/i13342-testing.check
@@ -0,0 +1 @@
+15: Pattern Match Exhaustivity: Thu, Fri
diff --git a/tests/patmat/i13342-testing.scala b/tests/patmat/i13342-testing.scala
new file mode 100644
index 000000000000..8ea22d79917f
--- /dev/null
+++ b/tests/patmat/i13342-testing.scala
@@ -0,0 +1,18 @@
+class C {
+  val bool: true      = true
+  val not1: None.type = None
+
+  def t1 = true match { case true => "inline true" }
+  def t2 = bool match { case true => "valdef true" }
+  def t3 = None match { case None => "inline None" }
+  def t4 = not1 match { case None => "valdef None" }
+
+  val monday: Day.Mon.type = Day.Mon
+  val someday: Day         = Day.Mon
+
+  def t5 = Day.Mon match { case Day.Mon => 1 case Day.Tue => 2 case Day.Wed => 3 }
+  def t6 = monday  match { case Day.Mon => 1 case Day.Tue => 2 case Day.Wed => 3 }
+  def t7 = someday match { case Day.Mon => 1 case Day.Tue => 2 case Day.Wed => 3 }
+}
+
+enum Day { case Mon, Tue, Wed, Thu, Fri }
diff --git a/tests/patmat/i13342.scala b/tests/patmat/i13342.scala
new file mode 100644
index 000000000000..d706442dd692
--- /dev/null
+++ b/tests/patmat/i13342.scala
@@ -0,0 +1,10 @@
+class C {
+  def m(x: true) = x match { // was: match may not be exhaustive.\nIt would fail on pattern case: false
+    case true => println("the one true path")
+  }
+
+  def n(x: true) = x match {
+    case true => 1
+    case false => 2 // was: no reachability warning on this case
+  }
+}