diff --git a/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala b/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala
index 6974f7f1b836..f8ccdcee4be5 100644
--- a/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala
+++ b/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala
@@ -148,7 +148,7 @@ class OrderingConstraint(private val boundsMap: ParamBounds,
   private def paramCount(entries: Array[Type]) = entries.length >> 1
 
   /** The type variable corresponding to parameter numbered `n`, null if none was created */
-  private def typeVar(entries: Array[Type], n: Int): Type =
+  private def typeVar(entries: Array[Type], n: Int): Type | Null =
     entries(paramCount(entries) + n)
 
   /** The `boundsMap` entry corresponding to `param` */
@@ -171,7 +171,7 @@ class OrderingConstraint(private val boundsMap: ParamBounds,
     val origin = tvar.origin
     val entries = boundsMap(origin.binder)
     val pnum = origin.paramNum
-    entries != null && isBounds(entries(pnum)) && (typeVar(entries, pnum) eq tvar)
+    entries != null && isBounds(entries(pnum)) && (typeVar(entries, pnum) eqn tvar)
   }
 
 // ---------- Dependency handling ----------------------------------------------
@@ -203,11 +203,13 @@ class OrderingConstraint(private val boundsMap: ParamBounds,
   def nonParamBounds(param: TypeParamRef)(using Context): TypeBounds =
     entry(param).bounds
 
-  def typeVarOfParam(param: TypeParamRef): Type = {
+  def typeVarOfParam(param: TypeParamRef): Type =
     val entries = boundsMap(param.binder)
     if entries == null then NoType
-    else typeVar(entries, param.paramNum)
-  }
+    else
+      val tvar = typeVar(entries, param.paramNum)
+      if tvar == null then NoType
+      else tvar
 
 // ---------- Adding TypeLambdas --------------------------------------------------
 
diff --git a/compiler/src/dotty/tools/dotc/core/TypeOps.scala b/compiler/src/dotty/tools/dotc/core/TypeOps.scala
index 2cfdd08128ce..3faab121637b 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeOps.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeOps.scala
@@ -145,7 +145,7 @@ object TypeOps:
         if normed.exists then normed else tp.map(simplify(_, theMap))
       case tp: TypeParamRef =>
         val tvar = ctx.typerState.constraint.typeVarOfParam(tp)
-        if (tvar.exists) tvar else tp
+        if tvar.exists then tvar else tp
       case  _: ThisType | _: BoundType =>
         tp
       case tp: AliasingBounds =>
diff --git a/tests/neg/i15272.scala b/tests/neg/i15272.scala
new file mode 100644
index 000000000000..1d380a3b5333
--- /dev/null
+++ b/tests/neg/i15272.scala
@@ -0,0 +1,11 @@
+    sealed trait EdgeN[+NT]
+    object EdgeN:
+      case class Head[+NT, +From <: NT, +To <: NT]    (from: From, to: To ) extends EdgeN[NT]
+      case class Cons[+NT, +From <: NT, +ToE <: EdgeN[NT]](from: From, to: ToE) extends EdgeN[NT]
+      final type InNodesTupleOf[NT, E <: EdgeN[NT]] <: Tuple = E match
+        case Cons[nt,from,toE] => from *: InNodesTupleOf[nt,toE]
+        case Head[nt,from ,to] => from *: EmptyTuple
+      def inNodesTuple[NT,E <: EdgeN[NT]](edge: E): InNodesTupleOf[NT,E] = edge match
+        case e: Cons[nt,from,toE] => e.from *: inNodesTuple[nt,toE](e.to) // error
+        case e: Head[nt,from,to] => e.from *: EmptyTuple
+    end EdgeN
\ No newline at end of file
diff --git a/tests/pos/i15183/decoder_1.scala b/tests/pos/i15183/decoder_1.scala
new file mode 100644
index 000000000000..532fd7246c3a
--- /dev/null
+++ b/tests/pos/i15183/decoder_1.scala
@@ -0,0 +1,14 @@
+import scala.deriving._
+
+sealed trait Decoder[T]
+object Decoder {
+  given Decoder[Double] = ???
+
+  inline given summonEmptyTuple[H]: Tuple.Map[EmptyTuple.type, Decoder] =
+    EmptyTuple
+
+  inline given summonTuple[H, T <: Tuple](using hd: Decoder[H], td: Tuple.Map[T, Decoder]): Tuple.Map[H *: T, Decoder] =
+    hd *: td
+
+  inline given derived[T](using m: Mirror.Of[T], d: Tuple.Map[m.MirroredElemTypes, Decoder]): Decoder[T] = ???
+}
diff --git a/tests/pos/i15183/test_2.scala b/tests/pos/i15183/test_2.scala
new file mode 100644
index 000000000000..2069d5637734
--- /dev/null
+++ b/tests/pos/i15183/test_2.scala
@@ -0,0 +1,12 @@
+// Fails in each cases below
+enum Env derives Decoder:
+  case Local,Sit,Prod
+
+enum Env2 derives Decoder:
+  case Local()
+  case Sit()
+  case Prod()
+
+enum Shape derives Decoder:
+  case Rectangle(width: Double, height: Double)
+  case Circle(radius: Double)