diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 38fd65cb4c54..eee0e802528c 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -2497,9 +2497,15 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
   def provablyDisjoint(tp1: Type, tp2: Type)(using Context): Boolean = trace(i"provable disjoint $tp1, $tp2", matchTypes) {
     // println(s"provablyDisjoint(${tp1.show}, ${tp2.show})")
 
-    def isEnumValueOrModule(ref: TermRef): Boolean =
+    def isEnumValue(ref: TermRef): Boolean =
       val sym = ref.termSymbol
-      sym.isAllOf(EnumCase, butNot=JavaDefined) || sym.is(Module)
+      sym.isAllOf(EnumCase, butNot=JavaDefined)
+
+    def isEnumValueOrModule(ref: TermRef): Boolean =
+      isEnumValue(ref) || ref.termSymbol.is(Module) || (ref.info match {
+        case tp: TermRef => isEnumValueOrModule(tp)
+        case _ => false
+      })
 
     /** Can we enumerate all instantiations of this type? */
     def isClosedSum(tp: Symbol): Boolean =
@@ -2512,8 +2518,21 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
     def decompose(sym: Symbol, tp: Type): List[Type] =
       sym.children.map(x => refineUsingParent(tp, x)).filter(_.exists)
 
+    def fullyInstantiated(tp: Type): Boolean = new TypeAccumulator[Boolean] {
+      override def apply(x: Boolean, t: Type) =
+        x && {
+          t match {
+            case tp: TypeRef if tp.symbol.isAbstractOrParamType => false
+            case _: SkolemType | _: TypeVar => false
+            case _ => foldOver(x, t)
+          }
+        }
+    }.apply(true, tp)
+
     (tp1.dealias, tp2.dealias) match {
-      case (tp1: TypeRef, tp2: TypeRef) if tp1.symbol == defn.SingletonClass || tp2.symbol == defn.SingletonClass =>
+      case (tp1: TypeRef, _) if tp1.symbol == defn.SingletonClass =>
+        false
+      case (_, tp2: TypeRef) if tp2.symbol == defn.SingletonClass =>
         false
       case (tp1: ConstantType, tp2: ConstantType) =>
         tp1 != tp2
@@ -2557,21 +2576,10 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
         // doesn't have type tags, meaning that users cannot write patterns
         // that do type tests on higher kinded types.
         def invariantDisjoint(tp1: Type, tp2: Type, tparam: TypeParamInfo): Boolean =
-          covariantDisjoint(tp1, tp2, tparam) || !isSameType(tp1, tp2) && {
-            // We can only trust a "no" from `isSameType` when both
-            // `tp1` and `tp2` are fully instantiated.
-            def fullyInstantiated(tp: Type): Boolean = new TypeAccumulator[Boolean] {
-              override def apply(x: Boolean, t: Type) =
-                x && {
-                  t match {
-                    case tp: TypeRef if tp.symbol.isAbstractOrParamType => false
-                    case _: SkolemType | _: TypeVar => false
-                    case _ => foldOver(x, t)
-                  }
-                }
-            }.apply(true, tp)
-            fullyInstantiated(tp1) && fullyInstantiated(tp2)
-          }
+          covariantDisjoint(tp1, tp2, tparam) ||
+          !isSameType(tp1, tp2) &&
+          fullyInstantiated(tp1) && // We can only trust a "no" from `isSameType` when
+          fullyInstantiated(tp2)    // both `tp1` and `tp2` are fully instantiated.
 
         args1.lazyZip(args2).lazyZip(tycon1.typeParams).exists {
           (arg1, arg2, tparam) =>
@@ -2608,11 +2616,10 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
         provablyDisjoint(tp1, gadtBounds(tp2.symbol).hi) || provablyDisjoint(tp1, tp2.superType)
       case (tp1: TermRef, tp2: TermRef) if isEnumValueOrModule(tp1) && isEnumValueOrModule(tp2) =>
         tp1.termSymbol != tp2.termSymbol
-      case (tp1: TermRef, tp2: TypeRef) if isEnumValueOrModule(tp1) && !tp1.classSymbols.exists(_.derivesFrom(tp2.classSymbol)) =>
-        // Note: enum values may have multiple parents
-        true
-      case (tp1: TypeRef, tp2: TermRef) if isEnumValueOrModule(tp2) && !tp2.classSymbols.exists(_.derivesFrom(tp1.classSymbol)) =>
-        true
+      case (tp1: TermRef, tp2: TypeRef) if isEnumValue(tp1) =>
+        fullyInstantiated(tp2) && !tp1.classSymbols.exists(_.derivesFrom(tp2.symbol))
+      case (tp1: TypeRef, tp2: TermRef) if isEnumValue(tp2) =>
+        fullyInstantiated(tp1) && !tp2.classSymbols.exists(_.derivesFrom(tp1.symbol))
       case (tp1: Type, tp2: Type) if defn.isTupleType(tp1) =>
         provablyDisjoint(tp1.toNestedPairs, tp2)
       case (tp1: Type, tp2: Type) if defn.isTupleType(tp2) =>
diff --git a/tests/neg/12549.scala b/tests/neg/12549.scala
new file mode 100644
index 000000000000..4e2a5531efa0
--- /dev/null
+++ b/tests/neg/12549.scala
@@ -0,0 +1,18 @@
+enum Bool {
+  case True
+  case False
+}
+
+import Bool.*
+
+type Not[B <: Bool] = B match {
+  case True.type => False.type
+  case False.type => True.type
+  case _ => "unreachable"
+}
+
+def foo[B <: Bool & Singleton]: Unit = {
+  implicitly[Not[B] =:= "unreachable"] // error
+
+  ()
+}