diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 7bb942e9ab6a..89ebfe99b967 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -166,6 +166,9 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
     try op finally frozenGadt = savedFrozenGadt
   }
 
+  private inline def inFrozenGadtAndConstraint[T](inline op: T): T =
+    inFrozenGadtIf(true)(inFrozenConstraint(op))
+
   protected def isSubType(tp1: Type, tp2: Type, a: ApproxState): Boolean = {
     val savedApprox = approx
     val savedLeftRoot = leftRoot
@@ -431,17 +434,10 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
           case Some(b) => return b
           case None =>
 
-        /** `recur` shouldn't normally be used with approximated types, according to its
-          * documentation. In the specific examples where this function is
-          * called, it is sound to do so as long as we freeze GADTs.
-          */
-        def recurInFrozenGadt(tp1: Type, tp2: Type) =
-          inFrozenGadt { recur(tp1, tp2) }
-
         def widenOK =
           (tp2.widenSingletons eq tp2)
           && (tp1.widenSingletons ne tp1)
-          && recurInFrozenGadt(tp1.widenSingletons, tp2)
+          && inFrozenGadtAndConstraint(recur(tp1.widenSingletons, tp2))
 
         def joinOK = tp2.dealiasKeepRefiningAnnots match {
           case tp2: AppliedType if !tp2.tycon.typeSymbol.isClass =>
@@ -449,7 +445,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
             // type parameter, we will instantiate `C` to `A` and then fail when comparing
             // with `B[Y]`. To do the right thing, we need to instantiate `C` to the
             // common superclass of `A` and `B`.
-            recurInFrozenGadt(tp1.join, tp2)
+            inFrozenGadtAndConstraint(recur(tp1.join, tp2))
           case _ =>
             false
         }
@@ -476,7 +472,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
         widenOK
         || joinOK
         || (tp1.isSoft || constrainRHSVars(tp2)) && recur(tp11, tp2) && recur(tp12, tp2)
-        || containsAnd(tp1) && recurInFrozenGadt(tp1.join, tp2)
+        || containsAnd(tp1) && inFrozenGadt(recur(tp1.join, tp2))
      case tp1: MatchType =>
         val reduced = tp1.reduced
         if (reduced.exists) recur(reduced, tp2) else thirdTry
diff --git a/compiler/src/dotty/tools/dotc/core/Types.scala b/compiler/src/dotty/tools/dotc/core/Types.scala
index 9273bef4b9f5..4f8f44b2528a 100644
--- a/compiler/src/dotty/tools/dotc/core/Types.scala
+++ b/compiler/src/dotty/tools/dotc/core/Types.scala
@@ -3104,7 +3104,10 @@ object Types {
 
     private def ensureAtomsComputed()(using Context): Unit =
       if atomsRunId != ctx.runId then
-        myAtoms = tp1.atoms | tp2.atoms
+        myAtoms =
+          if tp1.hasClassSymbol(defn.NothingClass) then tp2.atoms
+          else if tp2.hasClassSymbol(defn.NothingClass) then tp1.atoms
+          else tp1.atoms | tp2.atoms
         val tp1w = tp1.widenSingletons
         val tp2w = tp2.widenSingletons
         myWidened = if ((tp1 eq tp1w) && (tp2 eq tp2w)) this else tp1w | tp2w
diff --git a/scala3doc/test/dotty/dokka/SourceLinksTests.scala b/scala3doc/test/dotty/dokka/SourceLinksTests.scala
index 9b1567bfd12a..92fa9b1c7cb8 100644
--- a/scala3doc/test/dotty/dokka/SourceLinksTests.scala
+++ b/scala3doc/test/dotty/dokka/SourceLinksTests.scala
@@ -69,7 +69,6 @@ class SourceLinksTest:
         case (path: String, line: Int) => links.pathTo(projectRoot.resolve(path), line = Some(line))
         case (path: String, operation: Operation) => links.pathTo(projectRoot.resolve(path), operation = operation)
         case (path: String, line: Int, operation: Operation) => links.pathTo(projectRoot.resolve(path), operation = operation, line = Some(line))
-        case _ => ??? // needed due to handling of singleton types inside union types
 
       val expectedRes = expected match
         case s: String => Some(s)
diff --git a/tests/neg/singletonOrs.scala b/tests/neg/singletonOrs.scala
index cad48f524606..750722dba14e 100644
--- a/tests/neg/singletonOrs.scala
+++ b/tests/neg/singletonOrs.scala
@@ -24,7 +24,7 @@ object Get2As1 {
     def get2as11X:V = tuToV()(2)  // error
   }
   class Or11Nothing extends Or11X[Nothing]
-  def get2as1:1 = new Or11Nothing().get2as11X // error
+  def get2as1:1 = new Or11Nothing().get2as11X // ok
 
   def main(a:Array[String]) = {
     println(get2as1) // prints 2
diff --git a/tests/pos/i11003.scala b/tests/pos/i11003.scala
new file mode 100644
index 000000000000..3c67e7773bb0
--- /dev/null
+++ b/tests/pos/i11003.scala
@@ -0,0 +1,20 @@
+object Foo
+
+val x: Foo.type = Foo
+val y: Foo.type | Nothing = x
+val z: Foo.type = y
+val a: 1 | Nothing = 1
+val b: 1 = a
+
+val intSuper = summon[(Int | Nothing) <:< Int]
+val intSub = summon[Int <:< (Int | Nothing)]
+val intEq = summon[Int =:= (Int | Nothing)]
+
+val fooSuper = summon[(Foo.type | Nothing) <:< Foo.type]
+val fooSub = summon[Foo.type <:< (Foo.type | Nothing)]
+val fooEq = summon[Foo.type =:= (Foo.type | Nothing)]
+
+val oneSuper = summon[(1 | Nothing) <:< 1]
+val oneSub = summon[1 <:< (1 | Nothing)]
+val oneEq = summon[1 =:= (1 | Nothing)]
+