diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index a61bc0cf2a9a..fd000257c75c 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -600,8 +600,7 @@ class TypeComparer(initctx: Context) extends ConstraintHandling[AbsentContext] w
         compareTypeLambda
       case OrType(tp21, tp22) =>
         if (tp2.atoms.nonEmpty && canCompare(tp2.atoms))
-          return tp1.atoms.nonEmpty && tp1.atoms.subsetOf(tp2.atoms) ||
-            tp1.isRef(NothingClass)
+          return tp1.atoms.nonEmpty && tp1.atoms.subsetOf(tp2.atoms) || isSubType(tp1, NothingType)
 
         // The next clause handles a situation like the one encountered in i2745.scala.
         // We have:
diff --git a/compiler/src/dotty/tools/dotc/core/Types.scala b/compiler/src/dotty/tools/dotc/core/Types.scala
index 36f2d07dbc8c..bea3f53df929 100644
--- a/compiler/src/dotty/tools/dotc/core/Types.scala
+++ b/compiler/src/dotty/tools/dotc/core/Types.scala
@@ -1102,8 +1102,11 @@ object Types {
             }
           case _ => tp
         }
-        Set.empty + normalize(tp)
-      case tp: OrType => tp.atoms
+        val underlyingAtoms = tp.underlying.atoms
+        if (underlyingAtoms.isEmpty) Set.empty + normalize(tp)
+        else underlyingAtoms
+      case tp: ExprType => tp.resType.atoms
+      case tp: OrType => tp.atoms // `atoms` overridden in OrType
       case tp: AndType => tp.tp1.atoms & tp.tp2.atoms
       case _ => Set.empty
     }
diff --git a/tests/pos/singlesubtypes.scala b/tests/pos/singlesubtypes.scala
new file mode 100644
index 000000000000..bf4273669a02
--- /dev/null
+++ b/tests/pos/singlesubtypes.scala
@@ -0,0 +1,13 @@
+object E {
+  val a: String = ???
+  val b: String = ???
+}
+
+object Test {
+
+  val a: E.a.type = E.a
+  val b: E.b.type = E.b
+
+  val c: a.type | b.type = ???
+  val d: a.type | b.type = c
+}