diff --git a/compiler/src/dotty/tools/dotc/core/TypeApplications.scala b/compiler/src/dotty/tools/dotc/core/TypeApplications.scala
index ab216bfd147d..64b9a1f082ba 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeApplications.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeApplications.scala
@@ -310,6 +310,34 @@ class TypeApplications(val self: Type) extends AnyVal {
   def ensureLambdaSub(using Context): Type =
     if (isLambdaSub) self else EtaExpansion(self)
 
+
+  /** Convert a type constructor `TC` which has type parameters `X1, ..., Xn`
+   *  to `[X1, ..., Xn] -> TC[X1, ..., Xn]`.
+   */
+  def etaExpand(using Context): Type =
+    val tparams = self.typeParams
+    val resType = self.appliedTo(tparams.map(_.paramRef))
+    self.dealias match
+      case self: TypeRef if tparams.nonEmpty && self.symbol.isClass =>
+        val owner = self.symbol.owner
+        // Calling asSeenFrom on the type parameter infos is important
+        // so that class type references within another prefix have
+        // their type parameters' info fixed.
+        // e.g. from pos/i18569:
+        //    trait M1:
+        //      trait A
+        //      trait F[T <: A]
+        //    object M2 extends M1
+        // Type parameter T in M1.F has an upper bound of M1#A
+        // But eta-expanding M2.F should have type parameters with an upper-bound of M2.A.
+        // So we take the prefix M2.type and the F symbol's owner, M1,
+        // to call asSeenFrom on T's info.
+        HKTypeLambda(tparams.map(_.paramName))(
+          tl => tparams.map(p => HKTypeLambda.toPInfo(tl.integrate(tparams, p.paramInfo.asSeenFrom(self.prefix, owner)))),
+          tl => tl.integrate(tparams, resType))
+      case _ =>
+        HKTypeLambda.fromParams(tparams, resType)
+
   /** Eta expand if `self` is a (non-lambda) class reference and `bound` is a higher-kinded type */
   def EtaExpandIfHK(bound: Type)(using Context): Type = {
     val hkParams = bound.hkTypeParams
diff --git a/compiler/src/dotty/tools/dotc/core/Types.scala b/compiler/src/dotty/tools/dotc/core/Types.scala
index f2e000c2db73..f0ca272cce36 100644
--- a/compiler/src/dotty/tools/dotc/core/Types.scala
+++ b/compiler/src/dotty/tools/dotc/core/Types.scala
@@ -6073,7 +6073,7 @@ object Types extends TypeUtils {
     protected def range(lo: Type, hi: Type): Type =
       if variance > 0 then hi
       else if variance < 0 then
-        if (lo eq defn.NothingType) && hi.hasSimpleKind then
+        if (lo eq defn.NothingType) then
           // Approximate by Nothing & hi instead of just Nothing, in case the
           // approximated type is used as the prefix of another type (this would
           // lead to a type with a `NoDenotation` denot and a possible
@@ -6084,8 +6084,14 @@ object Types extends TypeUtils {
           // example if Nothing is the type of a parameter being depended on in
           // a MethodType)
           //
-          // Test case in tests/pos/i23530.scala
-          AndType(lo, hi)
+          // Test case in tests/pos/i23530.scala (and tests/pos/i23627.scala for
+          // the higher-kinded case which requires eta-expansion)
+          hi.etaExpand match
+            case expandedHi: HKTypeLambda =>
+              expandedHi.derivedLambdaType(resType = AndType(lo, expandedHi.resType))
+            case _ =>
+              // simple-kinded case
+              AndType(lo, hi)
         else
           lo
       else if lo `eq` hi then lo
diff --git a/tests/pos/i23627.scala b/tests/pos/i23627.scala
new file mode 100644
index 000000000000..1480a80c9c00
--- /dev/null
+++ b/tests/pos/i23627.scala
@@ -0,0 +1,18 @@
+trait TestContainer:
+  trait TestPath[T]:
+    type AbsMember
+
+  extension (path: TestPath[?])
+    infix def ext(color: path.AbsMember): Unit = ???
+    infix def ext(other: Int): Unit = ???
+
+object Repro:
+  val dc2: TestContainer = ???
+  import dc2.TestPath
+
+  def transition(path: TestPath[?])(using DummyImplicit): TestPath[?] = ???
+
+  def test: Unit =
+    val di: TestPath[?] = ???
+    // error
+    val z1 = transition(di).ext(1)