diff --git a/pkg/component/controller/workerconfig/reconciler.go b/pkg/component/controller/workerconfig/reconciler.go
index 15553748120c..ac8bdf5757e2 100644
--- a/pkg/component/controller/workerconfig/reconciler.go
+++ b/pkg/component/controller/workerconfig/reconciler.go
@@ -165,7 +165,7 @@ func (r *Reconciler) Start(context.Context) error {
 	// the update channel and apply those to the desired state. Changes will be
 	// applied whenever the last reconciled state differs from the desired
 	// state.
-	reconcilerCtx, cancelReconciler := context.WithCancel(context.Background())
+	reconcilerCtx, cancelReconciler := context.WithCancelCause(context.Background())
 	stopped := make(chan struct{})
 	apply := r.apply
 	go func() {
@@ -177,10 +177,10 @@ func (r *Reconciler) Start(context.Context) error {
 
 	go func() {
 		wait.UntilWithContext(reconcilerCtx, func(ctx context.Context) {
-			err := r.reconcileAPIServers(ctx, updates, stopped)
+			err := r.reconcileAPIServers(ctx, updates)
 			// Log any reconciliation errors, but only if they don't
 			// indicate that the reconciler has been stopped concurrently.
-			if err != nil && !errors.Is(err, reconcilerCtx.Err()) && !errors.Is(err, errStoppedConcurrently) {
+			if err != nil && !errors.Is(err, errStoppedConcurrently) {
 				r.log.WithError(err).Error("Failed to reconcile API server addresses")
 			}
 		}, 10*time.Second)
@@ -189,10 +189,10 @@ func (r *Reconciler) Start(context.Context) error {
 	// lease is acquired.
 	r.leaderElector.AddAcquiredLeaseCallback(func() {
 		go func() {
-			ctx, cancel := context.WithTimeout(context.Background(), 1*time.Minute)
+			ctx, cancel := context.WithTimeout(reconcilerCtx, 1*time.Minute)
 			defer cancel()
 
-			err := reconcile(ctx, updates, stopped, func(s *snapshot) {
+			err := reconcile(ctx, updates, func(s *snapshot) {
 				s.serial++
 			})
 
@@ -207,7 +207,7 @@ func (r *Reconciler) Start(context.Context) error {
 	// Store the started state
 	r.apply = nil
 	r.updates = updates
-	r.requestStop = cancelReconciler
+	r.requestStop = func() { cancelReconciler(errStoppedConcurrently) }
 	r.stopped = stopped
 	r.state = reconcilerStarted
 
@@ -236,8 +236,8 @@ func (r *Reconciler) runReconcileLoop(ctx context.Context, updates <-chan update
 	var desiredState, reconciledState snapshot
 
 	runReconciliation := func() error {
-		if err := ctx.Err(); err != nil {
-			return fmt.Errorf("%w while processing reconciliation", errStoppedConcurrently)
+		if err := context.Cause(ctx); err != nil {
+			return fmt.Errorf("%w while processing reconciliation", err)
 		}
 
 		if !r.leaderElector.IsLeader() {
@@ -322,7 +322,18 @@ func (r *Reconciler) Reconcile(ctx context.Context, cluster *v1beta1.ClusterConf
 
 	configSnapshot := takeConfigSnapshot(cluster.Spec)
 
-	return reconcile(ctx, updates, stopped, func(s *snapshot) {
+	ctx, cancel := context.WithCancelCause(ctx)
+	defer cancel(nil)
+
+	go func() {
+		select {
+		case <-stopped:
+			cancel(errStoppedConcurrently)
+		case <-ctx.Done():
+		}
+	}()
+
+	return reconcile(ctx, updates, func(s *snapshot) {
 		s.configSnapshot = &configSnapshot
 	})
 }
@@ -330,25 +341,21 @@ func (r *Reconciler) Reconcile(ctx context.Context, cluster *v1beta1.ClusterConf
 var errStoppedConcurrently = errors.New("stopped concurrently")
 
 // reconcile enqueues the given update and awaits its reconciliation.
-func reconcile(ctx context.Context, updates chan<- updateFunc, stopped <-chan struct{}, update func(*snapshot)) error {
+func reconcile(ctx context.Context, updates chan<- updateFunc, update func(*snapshot)) error {
 	recoDone := make(chan error, 1)
 
 	select {
 	case updates <- func(s *snapshot) chan<- error { update(s); return recoDone }:
 		break
-	case <-stopped:
-		return fmt.Errorf("%w while trying to enqueue state update", errStoppedConcurrently)
 	case <-ctx.Done():
-		return fmt.Errorf("%w while trying to enqueue state update", ctx.Err())
+		return fmt.Errorf("%w while trying to enqueue state update", context.Cause(ctx))
 	}
 
 	select {
 	case err := <-recoDone:
 		return err
-	case <-stopped:
-		return fmt.Errorf("%w while waiting for reconciliation to finish", errStoppedConcurrently)
 	case <-ctx.Done():
-		return fmt.Errorf("%w while waiting for reconciliation to finish", ctx.Err())
+		return fmt.Errorf("%w while waiting for reconciliation to finish", context.Cause(ctx))
 	}
 }
 
@@ -384,7 +391,7 @@ func (r *Reconciler) Stop() error {
 	return nil
 }
 
-func (r *Reconciler) reconcileAPIServers(ctx context.Context, updates chan<- updateFunc, stopped <-chan struct{}) error {
+func (r *Reconciler) reconcileAPIServers(ctx context.Context, updates chan<- updateFunc) error {
 	client, err := r.clientFactory.GetClient()
 	if err != nil {
 		return err
@@ -398,7 +405,7 @@ func (r *Reconciler) reconcileAPIServers(ctx context.Context, updates chan<- upd
 				return false, err
 			}
 
-			return false, reconcile(ctx, updates, stopped, func(s *snapshot) { s.apiServers = apiServers })
+			return false, reconcile(ctx, updates, func(s *snapshot) { s.apiServers = apiServers })
 		})
 }
 
diff --git a/pkg/component/controller/workerconfig/reconciler_test.go b/pkg/component/controller/workerconfig/reconciler_test.go
index c5162eb7373d..8fb65dd4c4a3 100644
--- a/pkg/component/controller/workerconfig/reconciler_test.go
+++ b/pkg/component/controller/workerconfig/reconciler_test.go
@@ -572,7 +572,7 @@ func TestReconciler_runReconcileLoop(t *testing.T) {
 		leaderElector: &leaderelector.Dummy{Leader: true},
 	}
 
-	ctx, cancel := context.WithTimeout(context.TODO(), 5*time.Second)
+	ctx, cancel := context.WithCancelCause(context.TODO())
 
 	// Prepare update channel for two updates.
 	updates, firstDone, secondDone := make(chan updateFunc, 2), make(chan error, 1), make(chan error, 1)
@@ -581,7 +581,7 @@ func TestReconciler_runReconcileLoop(t *testing.T) {
 	updates <- func(s *snapshot) chan<- error { return firstDone }
 
 	// Put in the second update that'll cancel the context.
-	updates <- func(s *snapshot) chan<- error { cancel(); return secondDone }
+	updates <- func(s *snapshot) chan<- error { cancel(errStoppedConcurrently); return secondDone }
 
 	underTest.runReconcileLoop(ctx, updates, nil)