diff --git a/controlplane/kubeadm/internal/controllers/controller.go b/controlplane/kubeadm/internal/controllers/controller.go
index 3e6bc71af9ea..c75f8e3d10e7 100644
--- a/controlplane/kubeadm/internal/controllers/controller.go
+++ b/controlplane/kubeadm/internal/controllers/controller.go
@@ -222,11 +222,22 @@ func (r *KubeadmControlPlaneReconciler) Reconcile(ctx context.Context, req ctrl.
 			reterr = kerrors.NewAggregate([]error{reterr, err})
 		}
 
-		// TODO: remove this as soon as we have a proper remote cluster cache in place.
-		// Make KCP to requeue in case status is not ready, so we can check for node status without waiting for a full resync (by default 10 minutes).
-		// Only requeue if we are not going in exponential backoff due to error, or if we are not already re-queueing, or if the object has a deletion timestamp.
-		if reterr == nil && !res.Requeue && res.RequeueAfter <= 0 && kcp.ObjectMeta.DeletionTimestamp.IsZero() {
-			if !kcp.Status.Ready {
+		if reterr == nil && kcp.ObjectMeta.DeletionTimestamp.IsZero() {
+			// TODO: remove this as soon as we have a proper remote cluster cache in place.
+			// Make KCP to requeue in case status is not ready, so we can check for node status without waiting for a full resync (by default 10 minutes).
+			// Only requeue if we are not going in exponential backoff due to error, or if we are not already re-queueing, or if the object has a deletion timestamp.
+			if !res.Requeue && res.RequeueAfter <= 0 {
+				if !kcp.Status.Ready {
+					res = ctrl.Result{RequeueAfter: 20 * time.Second}
+				}
+			}
+
+			// Make sure KCP gets requeued if ControlPlaneComponentsHealthyCondition is still false.
+			// Otherwise KCP would only get requeued when KCP or the Cluster gets a change or via reaching the resyncperiod.
+			// That would lead to a delay in provisioning MachineDeployments when preflight checks are enabled.
+			// The alternative solution to this requeue would be watching the relevant pods inside each workload
+			// cluster which would be very expensive.
+			if res.IsZero() && conditions.IsFalse(kcp, controlplanev1.ControlPlaneComponentsHealthyCondition) {
 				res = ctrl.Result{RequeueAfter: 20 * time.Second}
 			}
 		}