diff --git a/compiler/src/dotty/tools/dotc/cc/CaptureOps.scala b/compiler/src/dotty/tools/dotc/cc/CaptureOps.scala
index d31afe200263..37be4c76c8d1 100644
--- a/compiler/src/dotty/tools/dotc/cc/CaptureOps.scala
+++ b/compiler/src/dotty/tools/dotc/cc/CaptureOps.scala
@@ -222,19 +222,27 @@ extension (tp: Type)
     case tp: SingletonCaptureRef => tp.captureSetOfInfo
     case _ => CaptureSet.ofType(tp, followResult = false)
 
-  /** The deep capture set of a type.
-   *  For singleton capabilities `x` and reach capabilities `x*`, this is `{x*}`, provided
-   *  the underlying capture set resulting from traversing the type is non-empty.
-   *  For other types this is the union of all covariant capture sets embedded
-   *  in the type, as computed by `CaptureSet.ofTypeDeeply`.
+  /** The deep capture set of a type. This is by default the union of all
+   *  covariant capture sets embedded in the widened type, as computed by
+   *  `CaptureSet.ofTypeDeeply`. If that set is nonempty, and the type is
+   *  a singleton capability `x` or a reach capability `x*`, the deep capture
+   *  set can be narrowed to`{x*}`. However, A deep capture set should not be
+   *  narrowed to a reach capability `x*` if there are elements in the underlying
+   *  set that live longer than `x`. See `delayedRunops.scala` for a test case.
    */
   def deepCaptureSet(using Context): CaptureSet =
     val dcs = CaptureSet.ofTypeDeeply(tp.widen.stripCapturing)
+    def reachCanSubsumDcs =
+      dcs.isUniversal
+      || dcs.elems.forall(c => c.pathOwner.isContainedIn(tp.pathOwner))
     if dcs.isAlwaysEmpty then tp.captureSet
     else tp match
-      case tp @ ReachCapability(_) => tp.singletonCaptureSet
-      case tp: SingletonCaptureRef if tp.isTrackableRef => tp.reach.singletonCaptureSet
-      case _ => tp.captureSet ++ dcs
+      case tp @ ReachCapability(_) if reachCanSubsumDcs =>
+        tp.singletonCaptureSet
+      case tp: SingletonCaptureRef if tp.isTrackableRef && reachCanSubsumDcs =>
+        tp.reach.singletonCaptureSet
+      case _ =>
+        tp.captureSet ++ dcs
 
   /** A type capturing `ref` */
   def capturing(ref: CaptureRef)(using Context): Type =
@@ -277,8 +285,18 @@ extension (tp: Type)
   /** The first element of this path type */
   final def pathRoot(using Context): Type = tp.dealias match
     case tp1: NamedType if tp1.symbol.owner.isClass => tp1.prefix.pathRoot
+    case tp1 @ ReachCapability(tp2) => tp2.pathRoot
     case _ => tp
 
+  /** If this part starts with `C.this`, the class `C`.
+   *  Otherwise, if it starts with a reference `r`, `r`'s owner.
+   *  Otherwise NoSymbol.
+   */
+  final def pathOwner(using Context): Symbol = pathRoot match
+    case tp1: NamedType => tp1.symbol.owner
+    case tp1: ThisType => tp1.cls
+    case _ => NoSymbol
+
   /** If this is a unboxed capturing type with nonempty capture set, its boxed version.
    *  Or, if type is a TypeBounds of capturing types, the version where the bounds are boxed.
    *  The identity for all other types.
diff --git a/compiler/src/dotty/tools/dotc/cc/CheckCaptures.scala b/compiler/src/dotty/tools/dotc/cc/CheckCaptures.scala
index 66add1e7d9e3..af1e3c9cd6e8 100644
--- a/compiler/src/dotty/tools/dotc/cc/CheckCaptures.scala
+++ b/compiler/src/dotty/tools/dotc/cc/CheckCaptures.scala
@@ -1090,13 +1090,8 @@ class CheckCaptures extends Recheck, SymTransformer:
         (erefs /: erefs.elems): (erefs, eref) =>
           eref match
             case eref: ThisType if isPureContext(ctx.owner, eref.cls) =>
-              def isOuterRef(aref: Type): Boolean = aref.pathRoot match
-                case aref: NamedType => eref.cls.isProperlyContainedIn(aref.symbol.owner)
-                case aref: ThisType => eref.cls.isProperlyContainedIn(aref.cls)
-                case _ => false
-
-              val outerRefs = arefs.filter(isOuterRef)
-
+              val outerRefs = arefs.filter: aref =>
+                eref.cls.isProperlyContainedIn(aref.pathOwner)
               // Include implicitly added outer references in the capture set of the class of `eref`.
               for outerRef <- outerRefs.elems do
                 if !erefs.elems.contains(outerRef)
diff --git a/tests/neg-custom-args/captures/delayedRunops.check b/tests/neg-custom-args/captures/delayedRunops.check
new file mode 100644
index 000000000000..625f17663a4a
--- /dev/null
+++ b/tests/neg-custom-args/captures/delayedRunops.check
@@ -0,0 +1,5 @@
+-- Error: tests/neg-custom-args/captures/delayedRunops.scala:15:13 -----------------------------------------------------
+15 |      runOps(ops1)  // error
+   |             ^^^^
+   |             reference ops* is not included in the allowed capture set {}
+   |             of an enclosing function literal with expected type () -> Unit
diff --git a/tests/neg-custom-args/captures/delayedRunops.scala b/tests/neg-custom-args/captures/delayedRunops.scala
new file mode 100644
index 000000000000..1d1475806c52
--- /dev/null
+++ b/tests/neg-custom-args/captures/delayedRunops.scala
@@ -0,0 +1,15 @@
+import language.experimental.captureChecking
+
+  // ok
+  def runOps(ops: List[() => Unit]): Unit =
+    ops.foreach(op => op())
+
+  // ok
+  def delayedRunOps(ops: List[() => Unit]): () ->{ops*} Unit =
+    () => runOps(ops)
+
+  // unsound: impure operation pretended pure
+  def delayedRunOps1(ops: List[() => Unit]): () ->{} Unit =
+    () =>
+      val ops1 = ops
+      runOps(ops1)  // error
diff --git a/tests/neg-custom-args/captures/delayedRunops2.scala b/tests/neg-custom-args/captures/delayedRunops2.scala
new file mode 100644
index 000000000000..0c9aec20aaa3
--- /dev/null
+++ b/tests/neg-custom-args/captures/delayedRunops2.scala
@@ -0,0 +1,10 @@
+import language.experimental.captureChecking
+
+def runOps(ops: List[() => Unit]): Unit =
+  ops.foreach(op => op())
+
+def app[T, U](x: T, op: T => U): () ->{op} U =
+  () => op(x)
+
+def unsafeRunOps(ops: List[() => Unit]): () ->{} Unit =
+  app[List[() ->{ops*} Unit], Unit](ops, runOps) // error