diff --git a/controlplane/kubeadm/internal/controllers/remediation.go b/controlplane/kubeadm/internal/controllers/remediation.go
index e2c24d93d8c7..0441df9576e7 100644
--- a/controlplane/kubeadm/internal/controllers/remediation.go
+++ b/controlplane/kubeadm/internal/controllers/remediation.go
@@ -336,10 +336,24 @@ func (r *KubeadmControlPlaneReconciler) reconcileUnhealthyMachines(ctx context.C
 	return ctrl.Result{Requeue: true}, nil
 }
 
-// Gets the machine to be remediated, which is the oldest machine marked as unhealthy not yet provisioned (if any)
-// or the oldest machine marked as unhealthy.
+// Gets the machine which is marked as unhealthy and to be remediated, in the following order
+// Oldest machine which is not yet provisioned and has RemediateMachineAnnotation annotation
+// Oldest machine has RemediateMachineAnnotation annotation
+// Oldest machine not yet provisioned
+// Oldest machine marked as unhealthy
 func getMachineToBeRemediated(unhealthyMachines collections.Machines) *clusterv1.Machine {
-	machineToBeRemediated := unhealthyMachines.Filter(collections.Not(collections.HasNode())).Oldest()
+	machinesWithoutNode := unhealthyMachines.Filter(collections.Not(collections.HasNode()))
+	annotatedMachineWithoutNode := machinesWithoutNode.Filter(collections.HasAnnotationKey(clusterv1.RemediateMachineAnnotation)).Oldest()
+	if annotatedMachineWithoutNode != nil {
+		return annotatedMachineWithoutNode
+	}
+
+	annotatedMachine := unhealthyMachines.Filter(collections.HasAnnotationKey(clusterv1.RemediateMachineAnnotation)).Oldest()
+	if annotatedMachine != nil {
+		return annotatedMachine
+	}
+
+	machineToBeRemediated := machinesWithoutNode.Oldest()
 	if machineToBeRemediated == nil {
 		machineToBeRemediated = unhealthyMachines.Oldest()
 	}
diff --git a/controlplane/kubeadm/internal/controllers/remediation_test.go b/controlplane/kubeadm/internal/controllers/remediation_test.go
index 48a2ebd1b12c..9cde923dafff 100644
--- a/controlplane/kubeadm/internal/controllers/remediation_test.go
+++ b/controlplane/kubeadm/internal/controllers/remediation_test.go
@@ -42,6 +42,50 @@ import (
 )
 
 func TestGetMachineToBeRemediated(t *testing.T) {
+	t.Run("returns the oldest of the provisioning machines with RemediateMachineAnnotation", func(t *testing.T) {
+		g := NewWithT(t)
+
+		ns, err := env.CreateNamespace(ctx, "ns1")
+		g.Expect(err).ToNot(HaveOccurred())
+		defer func() {
+			g.Expect(env.Cleanup(ctx, ns)).To(Succeed())
+		}()
+
+		m1 := createMachine(ctx, g, ns.Name, "m1-unhealthy-", withMachineHealthCheckFailed())
+		m2 := createMachine(ctx, g, ns.Name, "m2-unhealthy-", withMachineHealthCheckFailed(), withoutNodeRef())
+		m3 := createMachine(ctx, g, ns.Name, "m3-unhealthy-", withMachineHealthCheckFailed(), withoutNodeRef())
+		m4 := createMachine(ctx, g, ns.Name, "m4-unhealthy-", withMachineHealthCheckFailed(), withoutNodeRef())
+
+		m1.SetAnnotations(map[string]string{clusterv1.RemediateMachineAnnotation: ""})
+		m2.SetAnnotations(map[string]string{clusterv1.RemediateMachineAnnotation: ""})
+		m3.SetAnnotations(map[string]string{clusterv1.RemediateMachineAnnotation: ""})
+
+		unhealthyMachines := collections.FromMachines(m1, m2, m3, m4)
+
+		g.Expect(getMachineToBeRemediated(unhealthyMachines).Name).To(HavePrefix("m2-unhealthy-"))
+	})
+
+	t.Run("returns the oldest machine with RemediateMachineAnnotation if there are no provisioning machines", func(t *testing.T) {
+		g := NewWithT(t)
+
+		ns, err := env.CreateNamespace(ctx, "ns1")
+		g.Expect(err).ToNot(HaveOccurred())
+		defer func() {
+			g.Expect(env.Cleanup(ctx, ns)).To(Succeed())
+		}()
+
+		m1 := createMachine(ctx, g, ns.Name, "m1-unhealthy-", withMachineHealthCheckFailed())
+		m2 := createMachine(ctx, g, ns.Name, "m2-unhealthy-", withMachineHealthCheckFailed())
+		m3 := createMachine(ctx, g, ns.Name, "m3-unhealthy-", withMachineHealthCheckFailed())
+
+		m1.SetAnnotations(map[string]string{clusterv1.RemediateMachineAnnotation: ""})
+		m2.SetAnnotations(map[string]string{clusterv1.RemediateMachineAnnotation: ""})
+
+		unhealthyMachines := collections.FromMachines(m1, m2, m3)
+
+		g.Expect(getMachineToBeRemediated(unhealthyMachines).Name).To(HavePrefix("m1-unhealthy-"))
+	})
+
 	t.Run("returns the oldest machine if there are no provisioning machines", func(t *testing.T) {
 		g := NewWithT(t)