diff --git a/controlplane/kubeadm/internal/workload_cluster_conditions.go b/controlplane/kubeadm/internal/workload_cluster_conditions.go
index f2e417f23b47..838fe8df5c20 100644
--- a/controlplane/kubeadm/internal/workload_cluster_conditions.go
+++ b/controlplane/kubeadm/internal/workload_cluster_conditions.go
@@ -961,8 +961,12 @@ func aggregateV1Beta2ConditionsFromMachinesToKCP(input aggregateV1Beta2Condition
 	for i := range input.controlPlane.Machines {
 		machine := input.controlPlane.Machines[i]
 		machineMessages := []string{}
+		conditionCount := 0
+		conditionMessages := sets.Set[string]{}
 		for _, condition := range input.machineConditions {
 			if machineCondition := v1beta2conditions.Get(machine, condition); machineCondition != nil {
+				conditionCount++
+				conditionMessages.Insert(machineCondition.Message)
 				switch machineCondition.Status {
 				case metav1.ConditionTrue:
 					kcpMachinesWithInfo.Insert(machine.Name)
@@ -985,6 +989,12 @@ func aggregateV1Beta2ConditionsFromMachinesToKCP(input aggregateV1Beta2Condition
 		}
 
 		if len(machineMessages) > 0 {
+			if conditionCount > 1 && len(conditionMessages) == 1 {
+				message := fmt.Sprintf("  * %s", conditionMessages.UnsortedList()[0])
+				messageMap[message] = append(messageMap[message], machine.Name)
+				continue
+			}
+
 			message := strings.Join(machineMessages, "\n")
 			messageMap[message] = append(messageMap[message], machine.Name)
 		}
diff --git a/controlplane/kubeadm/internal/workload_cluster_conditions_test.go b/controlplane/kubeadm/internal/workload_cluster_conditions_test.go
index 1e4a70ab2b71..7d6eb13c6951 100644
--- a/controlplane/kubeadm/internal/workload_cluster_conditions_test.go
+++ b/controlplane/kubeadm/internal/workload_cluster_conditions_test.go
@@ -804,10 +804,7 @@ func TestUpdateStaticPodConditions(t *testing.T) {
 				Status: metav1.ConditionUnknown,
 				Reason: controlplanev1.KubeadmControlPlaneControlPlaneComponentsHealthUnknownV1Beta2Reason,
 				Message: "* Machine m1:\n" +
-					"  * APIServerPodHealthy: Waiting for GenericInfraMachine to report spec.providerID\n" +
-					"  * ControllerManagerPodHealthy: Waiting for GenericInfraMachine to report spec.providerID\n" +
-					"  * SchedulerPodHealthy: Waiting for GenericInfraMachine to report spec.providerID\n" +
-					"  * EtcdPodHealthy: Waiting for GenericInfraMachine to report spec.providerID",
+					"  * Waiting for GenericInfraMachine to report spec.providerID",
 			},
 			expectedMachineV1Beta2Conditions: map[string][]metav1.Condition{
 				"m1": {
@@ -837,10 +834,7 @@ func TestUpdateStaticPodConditions(t *testing.T) {
 				Status: metav1.ConditionUnknown,
 				Reason: controlplanev1.KubeadmControlPlaneControlPlaneComponentsHealthUnknownV1Beta2Reason,
 				Message: "* Machine m1:\n" +
-					"  * APIServerPodHealthy: Waiting for a Node with spec.providerID dummy-provider-id to exist\n" +
-					"  * ControllerManagerPodHealthy: Waiting for a Node with spec.providerID dummy-provider-id to exist\n" +
-					"  * SchedulerPodHealthy: Waiting for a Node with spec.providerID dummy-provider-id to exist\n" +
-					"  * EtcdPodHealthy: Waiting for a Node with spec.providerID dummy-provider-id to exist",
+					"  * Waiting for a Node with spec.providerID dummy-provider-id to exist",
 			},
 			expectedMachineV1Beta2Conditions: map[string][]metav1.Condition{
 				"m1": {
@@ -891,10 +885,7 @@ func TestUpdateStaticPodConditions(t *testing.T) {
 				Status: metav1.ConditionUnknown,
 				Reason: controlplanev1.KubeadmControlPlaneControlPlaneComponentsHealthUnknownV1Beta2Reason,
 				Message: "* Machine m1:\n" +
-					"  * APIServerPodHealthy: Node n1 is unreachable\n" +
-					"  * ControllerManagerPodHealthy: Node n1 is unreachable\n" +
-					"  * SchedulerPodHealthy: Node n1 is unreachable\n" +
-					"  * EtcdPodHealthy: Node n1 is unreachable",
+					"  * Node n1 is unreachable",
 			},
 			expectedMachineV1Beta2Conditions: map[string][]metav1.Condition{
 				"m1": {
@@ -922,10 +913,7 @@ func TestUpdateStaticPodConditions(t *testing.T) {
 				Status: metav1.ConditionUnknown,
 				Reason: controlplanev1.KubeadmControlPlaneControlPlaneComponentsHealthUnknownV1Beta2Reason,
 				Message: "* Machine m1:\n" +
-					"  * APIServerPodHealthy: Waiting for GenericInfraMachine to report spec.providerID\n" +
-					"  * ControllerManagerPodHealthy: Waiting for GenericInfraMachine to report spec.providerID\n" +
-					"  * SchedulerPodHealthy: Waiting for GenericInfraMachine to report spec.providerID\n" +
-					"  * EtcdPodHealthy: Waiting for GenericInfraMachine to report spec.providerID",
+					"  * Waiting for GenericInfraMachine to report spec.providerID",
 			},
 			expectedMachineV1Beta2Conditions: map[string][]metav1.Condition{
 				"m1": {
@@ -958,10 +946,7 @@ func TestUpdateStaticPodConditions(t *testing.T) {
 				Status: metav1.ConditionUnknown,
 				Reason: controlplanev1.KubeadmControlPlaneControlPlaneComponentsHealthUnknownV1Beta2Reason,
 				Message: "* Machine m1:\n" +
-					"  * APIServerPodHealthy: Node n1 does not exist\n" +
-					"  * ControllerManagerPodHealthy: Node n1 does not exist\n" +
-					"  * SchedulerPodHealthy: Node n1 does not exist\n" +
-					"  * EtcdPodHealthy: Node n1 does not exist",
+					"  * Node n1 does not exist",
 			},
 			expectedMachineV1Beta2Conditions: map[string][]metav1.Condition{
 				"m1": {