diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 465978d329e6..2e7db9981531 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -3151,7 +3151,7 @@ class TrackingTypeComparer(initctx: Context) extends TypeComparer(initctx) {
               case redux =>
                 MatchResult.Reduced(redux.simplified)
           case _ =>
-            MatchResult.Reduced(body)
+            MatchResult.Reduced(body.simplified)
 
       if caseLambda.exists && matches(canWidenAbstract = false) then
         redux(canApprox = true)
diff --git a/tests/pos/i16596.scala b/tests/pos/i16596.scala
new file mode 100644
index 000000000000..36e20d1cf2de
--- /dev/null
+++ b/tests/pos/i16596.scala
@@ -0,0 +1,7 @@
+import scala.compiletime.ops.int
+
+type Count[N,T] <: Tuple = (N,T) match
+  case (0,T)      => EmptyTuple
+  case (N,T)      => T *: Count[int.-[N, 1], T]
+
+val a: Count[3, Int] = (1, 2, 3)