diff --git a/compiler/src/dotty/tools/dotc/cc/CaptureSet.scala b/compiler/src/dotty/tools/dotc/cc/CaptureSet.scala
index ee94d9bf1d31..1eb6744a39b0 100644
--- a/compiler/src/dotty/tools/dotc/cc/CaptureSet.scala
+++ b/compiler/src/dotty/tools/dotc/cc/CaptureSet.scala
@@ -588,6 +588,9 @@ object CaptureSet:
     cs.mutability = Mutability.Reader
     cs
 
+  class EmptyOfBoxed(val tp1: Type, val tp2: Type) extends Const(emptyRefs):
+    override def toString = "{} of boxed mismatch"
+
   /** The universal capture set `{cap}` */
   def universal(using Context): Const =
     Const(SimpleIdentitySet(GlobalCap))
@@ -1341,15 +1344,19 @@ object CaptureSet:
       case _ =>
         false
 
-    /** An include failure F1 covers another include failure F2 unless F2
-     *  strictly subsumes F1, which means they describe the same capture sets
-     *  and the element in F2 is more specific than the element in F1.
+    /** An include failure F1 covers another include failure F2 unless one
+     *  of the following two conditons holds:
+     *   1. F2 strictly subsumes F1, which means they describe the same capture sets
+     *      and the element in F2 is more specific than the element in F1.
+     *   2. Both F1 and F2 are the empty set, but only F2 is an empty set synthesized
+     *      when comparing types with different box status
      */
     override def covers(other: Note)(using Context) = other match
       case other @ IncludeFailure(cs1, elem1, _) =>
         val strictlySubsumes =
           cs.elems == cs1.elems
-          && elem1.singletonCaptureSet.mightSubcapture(elem.singletonCaptureSet)
+          && (elem1.singletonCaptureSet.mightSubcapture(elem.singletonCaptureSet)
+              || cs1.isInstanceOf[EmptyOfBoxed] && !cs.isInstanceOf[EmptyOfBoxed])
         !strictlySubsumes
       case _ => false
 
@@ -1390,6 +1397,11 @@ object CaptureSet:
         else
           trailing:
             i"capability ${elem.showAsCapability} cannot be included in capture set $cs"
+      case cs: EmptyOfBoxed =>
+        trailing:
+          val (boxed, unboxed) =
+            if cs.tp1.isBoxedCapturing then (cs.tp1, cs.tp2) else (cs.tp2, cs.tp1)
+          i"${cs.tp1} does not conform to ${cs.tp2} because $boxed is boxed but $unboxed is not"
       case _ =>
         def why =
           val reasons = cs.elems.toList.collect:
diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 6a7e4733f9d9..b9e57445ce94 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -550,10 +550,15 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
             || !ctx.mode.is(Mode.CheckBoundsOrSelfType) && tp1.isAlwaysPure
             || parent1.isSingleton && refs1.elems.forall(parent1 eq _)
           then
+            def remainsBoxed1 = parent1.isBoxedCapturing || parent1.dealias.match
+              case parent1: TypeRef =>
+                parent1.superType.isBoxedCapturing
+                // When comparing a type parameter with boxed upper bound on the left
+                // we should not strip the box on the right. See i24543.scala.
+              case _ =>
+                false
             val tp2a =
-              if tp1.isBoxedCapturing && !parent1.isBoxedCapturing
-              then tp2.unboxed
-              else tp2
+              if tp1.isBoxedCapturing && !remainsBoxed1 then tp2.unboxed else tp2
             recur(parent1, tp2a)
           else thirdTry
         compareCapturing
@@ -2915,7 +2920,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
         case _ =>
     subc
     && (tp1.isBoxedCapturing == tp2.isBoxedCapturing
-        || refs1.subCaptures(CaptureSet.empty, makeVarState()))
+        || refs1.subCaptures(CaptureSet.EmptyOfBoxed(tp1, tp2), makeVarState()))
 
   protected def logUndoAction(action: () => Unit) =
     undoLog += action
diff --git a/tests/neg-custom-args/captures/eta.check b/tests/neg-custom-args/captures/eta.check
index dfce53accd4d..09878f84135d 100644
--- a/tests/neg-custom-args/captures/eta.check
+++ b/tests/neg-custom-args/captures/eta.check
@@ -4,6 +4,6 @@
   |         Found:    (g : () -> A)
   |         Required: () -> Proc^{f}
   |
-  |         Note that capability f is not included in capture set {}.
+  |         Note that () ->{f} Unit does not conform to Proc^{f} because () ->{f} Unit is boxed but Proc^{f} is not.
   |
   | longer explanation available when compiling with `-explain`
diff --git a/tests/pos-custom-args/captures/i24543.scala b/tests/pos-custom-args/captures/i24543.scala
new file mode 100644
index 000000000000..e09607cbf53c
--- /dev/null
+++ b/tests/pos-custom-args/captures/i24543.scala
@@ -0,0 +1,12 @@
+import scala.language.experimental.captureChecking
+
+class Ref
+case class Box[T](elem: T)
+
+def h1[T <: Ref^](x: Box[T]): Unit =
+  val y: (Ref^, Int) = (x.elem, 1) // was error
+
+def h2[T <: Ref^](x: List[T]): (Ref^, Int) = (x.head, 1) // was error
+
+
+
diff --git a/tests/pos-custom-args/captures/i24543a.scala b/tests/pos-custom-args/captures/i24543a.scala
new file mode 100644
index 000000000000..034a45db2df0
--- /dev/null
+++ b/tests/pos-custom-args/captures/i24543a.scala
@@ -0,0 +1,9 @@
+import scala.language.experimental.captureChecking
+class Ref
+case class Box[+T](elem: T)
+
+def test1(a: Ref^): Unit =
+  def hh[T <: Ref^{a}](x: Box[T]): Unit =
+    val y: (Ref^{a}, Int) = (x.elem, 1)
+    val z = (x.elem, 1)
+    val _: (Ref^{a}, Int) = z