diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 8fc6307c426c..ee304e9c619f 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -3681,19 +3681,36 @@ class MatchReducer(initctx: Context) extends TypeComparer(initctx) {
 
             stableScrut.member(typeMemberName) match
               case denot: SingleDenotation if denot.exists =>
-                val info = denot.info match
-                  case alias: AliasingBounds           => alias.alias        // Extract the alias
-                  case ClassInfo(prefix, cls, _, _, _) => prefix.select(cls) // Re-select the class from the prefix
-                  case info => info // Notably, RealTypeBounds, which will eventually give a MatchResult.NoInstances
-                val info1 = stableScrut match
+                val info = stableScrut match
                   case skolem: SkolemType =>
-                    dropSkolem(info, skolem).orElse:
-                      info match
-                        case info: TypeBounds  => info                       // Will already trigger a MatchResult.NoInstances
-                        case _                 => RealTypeBounds(info, info) // Explicitly trigger a MatchResult.NoInstances
-                  case _ => info
-                rec(capture, info1, variance = 0, scrutIsWidenedAbstract)
+                    /* If it is a skolem type, we cannot have class selections nor
+                     * abstract type selections. If it is an alias, we try to remove
+                     * any reference to the skolem from the right-hand-side. If that
+                     * succeeds, we take the result, otherwise we fail as not-specific.
+                     */
+                    def adaptToTriggerNotSpecific(info: Type): Type = info match
+                      case info: TypeBounds => info
+                      case _                => RealTypeBounds(info, info)
+
+                    denot.info match
+                      case denotInfo: AliasingBounds =>
+                        val alias = denotInfo.alias
+                        dropSkolem(alias, skolem).orElse(adaptToTriggerNotSpecific(alias))
+                      case ClassInfo(prefix, cls, _, _, _) =>
+                        // for clean error messages
+                        adaptToTriggerNotSpecific(prefix.select(cls))
+                      case denotInfo =>
+                        adaptToTriggerNotSpecific(denotInfo)
+
+                  case _ =>
+                    // The scrutinee type is truly stable. We select the type member directly on it.
+                    stableScrut.select(typeMemberName)
+                end info
+
+                rec(capture, info, variance = 0, scrutIsWidenedAbstract)
+
               case _ =>
+                // The type member was not found; no match
                 false
       end rec
 
diff --git a/tests/pos/i21402.scala b/tests/pos/i21402.scala
new file mode 100644
index 000000000000..4ddf201ef8b4
--- /dev/null
+++ b/tests/pos/i21402.scala
@@ -0,0 +1,41 @@
+abstract class AbstractServiceKey:
+  type Protocol
+
+abstract class ServiceKey[T] extends AbstractServiceKey:
+  type Protocol = T
+
+type Aux[P] = AbstractServiceKey { type Protocol = P }
+type Service[K <: Aux[?]] = K match
+  case Aux[t] => ActorRef[t]
+type Subscriber[K <: Aux[?]] = K match
+  case Aux[t] => ActorRef[ReceptionistMessages.Listing[t]]
+
+trait ActorRef[-T]
+
+object ReceptionistMessages:
+  final case class Listing[T](key: ServiceKey[T])
+
+class TypedMultiMap[T <: AnyRef, K[_ <: T]]:
+  def get(key: T): Set[K[key.type]] = ???
+  transparent inline def getInlined(key: T): Set[K[key.type]] = ???
+  inline def inserted(key: T, value: K[key.type]): TypedMultiMap[T, K] = ???
+
+object LocalReceptionist {
+  final case class State(
+      services: TypedMultiMap[AbstractServiceKey, Service],
+      subscriptions: TypedMultiMap[AbstractServiceKey, Subscriber]
+  ):
+    def testInsert(key: AbstractServiceKey)(serviceInstance: ActorRef[key.Protocol]): State = {
+      val fails = services.inserted(key, serviceInstance) // error
+      ???
+    }
+
+  def testGet[T](key: AbstractServiceKey): Unit = {
+    val newState: State = ???
+    val fails: Set[ActorRef[key.Protocol]] = newState.services.get(key) // error
+    val works: Set[ActorRef[key.Protocol]] = newState.services.getInlined(key) // workaround
+
+    val fails2: Set[ActorRef[ReceptionistMessages.Listing[key.Protocol]]] = newState.subscriptions.get(key) // error
+    val works2: Set[ActorRef[ReceptionistMessages.Listing[key.Protocol]]] = newState.subscriptions.getInlined(key) // workaround
+  }
+}