diff --git a/api/v1alpha3/conversion.go b/api/v1alpha3/conversion.go
index d761d7adc942..4b3c5dd99e9f 100644
--- a/api/v1alpha3/conversion.go
+++ b/api/v1alpha3/conversion.go
@@ -97,6 +97,7 @@ func (src *Machine) ConvertTo(dstRaw conversion.Hub) error {
 		return err
 	}
 
+	dst.Spec.NodeDeletionTimeout = restored.Spec.NodeDeletionTimeout
 	dst.Status.NodeInfo = restored.Status.NodeInfo
 	return nil
 }
@@ -139,6 +140,7 @@ func (src *MachineSet) ConvertTo(dstRaw conversion.Hub) error {
 	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
 		return err
 	}
+	dst.Spec.Template.Spec.NodeDeletionTimeout = restored.Spec.Template.Spec.NodeDeletionTimeout
 	dst.Status.Conditions = restored.Status.Conditions
 	return nil
 }
@@ -192,6 +194,7 @@ func (src *MachineDeployment) ConvertTo(dstRaw conversion.Hub) error {
 		dst.Spec.Strategy.RollingUpdate.DeletePolicy = restored.Spec.Strategy.RollingUpdate.DeletePolicy
 	}
 
+	dst.Spec.Template.Spec.NodeDeletionTimeout = restored.Spec.Template.Spec.NodeDeletionTimeout
 	dst.Status.Conditions = restored.Status.Conditions
 	return nil
 }
@@ -304,6 +307,11 @@ func Convert_v1beta1_MachineStatus_To_v1alpha3_MachineStatus(in *clusterv1.Machi
 	return autoConvert_v1beta1_MachineStatus_To_v1alpha3_MachineStatus(in, out, s)
 }
 
+func Convert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(in *clusterv1.MachineSpec, out *MachineSpec, s apiconversion.Scope) error {
+	// spec.nodeDeletionTimeout has been added with v1beta1.
+	return autoConvert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(in, out, s)
+}
+
 func Convert_v1beta1_MachineDeploymentStatus_To_v1alpha3_MachineDeploymentStatus(in *clusterv1.MachineDeploymentStatus, out *MachineDeploymentStatus, s apiconversion.Scope) error {
 	// Status.Conditions was introduced in v1alpha4, thus requiring a custom conversion function; the values is going to be preserved in an annotation thus allowing roundtrip without loosing informations
 	return autoConvert_v1beta1_MachineDeploymentStatus_To_v1alpha3_MachineDeploymentStatus(in, out, s)
diff --git a/api/v1alpha3/zz_generated.conversion.go b/api/v1alpha3/zz_generated.conversion.go
index 4d3cbed70601..9661e6cc3f18 100644
--- a/api/v1alpha3/zz_generated.conversion.go
+++ b/api/v1alpha3/zz_generated.conversion.go
@@ -270,11 +270,6 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
-	if err := s.AddGeneratedConversionFunc((*v1beta1.MachineSpec)(nil), (*MachineSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
-		return Convert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(a.(*v1beta1.MachineSpec), b.(*MachineSpec), scope)
-	}); err != nil {
-		return err
-	}
 	if err := s.AddGeneratedConversionFunc((*MachineTemplateSpec)(nil), (*v1beta1.MachineTemplateSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1alpha3_MachineTemplateSpec_To_v1beta1_MachineTemplateSpec(a.(*MachineTemplateSpec), b.(*v1beta1.MachineTemplateSpec), scope)
 	}); err != nil {
@@ -355,6 +350,11 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
+	if err := s.AddConversionFunc((*v1beta1.MachineSpec)(nil), (*MachineSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
+		return Convert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(a.(*v1beta1.MachineSpec), b.(*MachineSpec), scope)
+	}); err != nil {
+		return err
+	}
 	if err := s.AddConversionFunc((*v1beta1.MachineStatus)(nil), (*MachineStatus)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1beta1_MachineStatus_To_v1alpha3_MachineStatus(a.(*v1beta1.MachineStatus), b.(*MachineStatus), scope)
 	}); err != nil {
@@ -1221,14 +1221,10 @@ func autoConvert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(in *v1beta1.Machine
 	out.ProviderID = (*string)(unsafe.Pointer(in.ProviderID))
 	out.FailureDomain = (*string)(unsafe.Pointer(in.FailureDomain))
 	out.NodeDrainTimeout = (*metav1.Duration)(unsafe.Pointer(in.NodeDrainTimeout))
+	// WARNING: in.NodeDeletionTimeout requires manual conversion: does not exist in peer-type
 	return nil
 }
 
-// Convert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec is an autogenerated conversion function.
-func Convert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(in *v1beta1.MachineSpec, out *MachineSpec, s conversion.Scope) error {
-	return autoConvert_v1beta1_MachineSpec_To_v1alpha3_MachineSpec(in, out, s)
-}
-
 func autoConvert_v1alpha3_MachineStatus_To_v1beta1_MachineStatus(in *MachineStatus, out *v1beta1.MachineStatus, s conversion.Scope) error {
 	out.NodeRef = (*v1.ObjectReference)(unsafe.Pointer(in.NodeRef))
 	out.LastUpdated = (*metav1.Time)(unsafe.Pointer(in.LastUpdated))
diff --git a/api/v1alpha4/conversion.go b/api/v1alpha4/conversion.go
index 3bfb31ba0949..5f789ae6f000 100644
--- a/api/v1alpha4/conversion.go
+++ b/api/v1alpha4/conversion.go
@@ -131,13 +131,33 @@ func (dst *ClusterClassList) ConvertFrom(srcRaw conversion.Hub) error {
 func (src *Machine) ConvertTo(dstRaw conversion.Hub) error {
 	dst := dstRaw.(*clusterv1.Machine)
 
-	return Convert_v1alpha4_Machine_To_v1beta1_Machine(src, dst, nil)
+	if err := Convert_v1alpha4_Machine_To_v1beta1_Machine(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Manually restore data.
+	restored := &clusterv1.Machine{}
+	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
+		return err
+	}
+
+	dst.Spec.NodeDeletionTimeout = restored.Spec.NodeDeletionTimeout
+	return nil
 }
 
 func (dst *Machine) ConvertFrom(srcRaw conversion.Hub) error {
 	src := srcRaw.(*clusterv1.Machine)
 
-	return Convert_v1beta1_Machine_To_v1alpha4_Machine(src, dst, nil)
+	if err := Convert_v1beta1_Machine_To_v1alpha4_Machine(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Preserve Hub data on down-conversion except for metadata
+	if err := utilconversion.MarshalData(src, dst); err != nil {
+		return err
+	}
+
+	return nil
 }
 
 func (src *MachineList) ConvertTo(dstRaw conversion.Hub) error {
@@ -155,13 +175,29 @@ func (dst *MachineList) ConvertFrom(srcRaw conversion.Hub) error {
 func (src *MachineSet) ConvertTo(dstRaw conversion.Hub) error {
 	dst := dstRaw.(*clusterv1.MachineSet)
 
-	return Convert_v1alpha4_MachineSet_To_v1beta1_MachineSet(src, dst, nil)
+	if err := Convert_v1alpha4_MachineSet_To_v1beta1_MachineSet(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Manually restore data.
+	restored := &clusterv1.MachineSet{}
+	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
+		return err
+	}
+
+	dst.Spec.Template.Spec.NodeDeletionTimeout = restored.Spec.Template.Spec.NodeDeletionTimeout
+	return nil
 }
 
 func (dst *MachineSet) ConvertFrom(srcRaw conversion.Hub) error {
 	src := srcRaw.(*clusterv1.MachineSet)
 
-	return Convert_v1beta1_MachineSet_To_v1alpha4_MachineSet(src, dst, nil)
+	if err := Convert_v1beta1_MachineSet_To_v1alpha4_MachineSet(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Preserve Hub data on down-conversion except for metadata
+	return utilconversion.MarshalData(src, dst)
 }
 
 func (src *MachineSetList) ConvertTo(dstRaw conversion.Hub) error {
@@ -179,13 +215,29 @@ func (dst *MachineSetList) ConvertFrom(srcRaw conversion.Hub) error {
 func (src *MachineDeployment) ConvertTo(dstRaw conversion.Hub) error {
 	dst := dstRaw.(*clusterv1.MachineDeployment)
 
-	return Convert_v1alpha4_MachineDeployment_To_v1beta1_MachineDeployment(src, dst, nil)
+	if err := Convert_v1alpha4_MachineDeployment_To_v1beta1_MachineDeployment(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Manually restore data.
+	restored := &clusterv1.MachineDeployment{}
+	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
+		return err
+	}
+
+	dst.Spec.Template.Spec.NodeDeletionTimeout = restored.Spec.Template.Spec.NodeDeletionTimeout
+	return nil
 }
 
 func (dst *MachineDeployment) ConvertFrom(srcRaw conversion.Hub) error {
 	src := srcRaw.(*clusterv1.MachineDeployment)
 
-	return Convert_v1beta1_MachineDeployment_To_v1alpha4_MachineDeployment(src, dst, nil)
+	if err := Convert_v1beta1_MachineDeployment_To_v1alpha4_MachineDeployment(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Preserve Hub data on down-conversion except for metadata
+	return utilconversion.MarshalData(src, dst)
 }
 
 func (src *MachineDeploymentList) ConvertTo(dstRaw conversion.Hub) error {
@@ -234,6 +286,11 @@ func Convert_v1beta1_ClusterClassSpec_To_v1alpha4_ClusterClassSpec(in *clusterv1
 	return autoConvert_v1beta1_ClusterClassSpec_To_v1alpha4_ClusterClassSpec(in, out, s)
 }
 
+func Convert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(in *clusterv1.MachineSpec, out *MachineSpec, s apiconversion.Scope) error {
+	// spec.nodeDeletionTimeout has been added with v1beta1.
+	return autoConvert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(in, out, s)
+}
+
 func Convert_v1beta1_Topology_To_v1alpha4_Topology(in *clusterv1.Topology, out *Topology, s apiconversion.Scope) error {
 	// spec.topology.variables has been added with v1beta1.
 	return autoConvert_v1beta1_Topology_To_v1alpha4_Topology(in, out, s)
diff --git a/api/v1alpha4/zz_generated.conversion.go b/api/v1alpha4/zz_generated.conversion.go
index a8aeec191bca..9a9e3d3dc1ab 100644
--- a/api/v1alpha4/zz_generated.conversion.go
+++ b/api/v1alpha4/zz_generated.conversion.go
@@ -375,11 +375,6 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
-	if err := s.AddGeneratedConversionFunc((*v1beta1.MachineSpec)(nil), (*MachineSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
-		return Convert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(a.(*v1beta1.MachineSpec), b.(*MachineSpec), scope)
-	}); err != nil {
-		return err
-	}
 	if err := s.AddGeneratedConversionFunc((*v1beta1.MachineStatus)(nil), (*MachineStatus)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1beta1_MachineStatus_To_v1alpha4_MachineStatus(a.(*v1beta1.MachineStatus), b.(*MachineStatus), scope)
 	}); err != nil {
@@ -475,6 +470,11 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
+	if err := s.AddConversionFunc((*v1beta1.MachineSpec)(nil), (*MachineSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
+		return Convert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(a.(*v1beta1.MachineSpec), b.(*MachineSpec), scope)
+	}); err != nil {
+		return err
+	}
 	if err := s.AddConversionFunc((*v1beta1.Topology)(nil), (*Topology)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1beta1_Topology_To_v1alpha4_Topology(a.(*v1beta1.Topology), b.(*Topology), scope)
 	}); err != nil {
@@ -1084,7 +1084,17 @@ func Convert_v1beta1_MachineDeploymentClassTemplate_To_v1alpha4_MachineDeploymen
 
 func autoConvert_v1alpha4_MachineDeploymentList_To_v1beta1_MachineDeploymentList(in *MachineDeploymentList, out *v1beta1.MachineDeploymentList, s conversion.Scope) error {
 	out.ListMeta = in.ListMeta
-	out.Items = *(*[]v1beta1.MachineDeployment)(unsafe.Pointer(&in.Items))
+	if in.Items != nil {
+		in, out := &in.Items, &out.Items
+		*out = make([]v1beta1.MachineDeployment, len(*in))
+		for i := range *in {
+			if err := Convert_v1alpha4_MachineDeployment_To_v1beta1_MachineDeployment(&(*in)[i], &(*out)[i], s); err != nil {
+				return err
+			}
+		}
+	} else {
+		out.Items = nil
+	}
 	return nil
 }
 
@@ -1095,7 +1105,17 @@ func Convert_v1alpha4_MachineDeploymentList_To_v1beta1_MachineDeploymentList(in
 
 func autoConvert_v1beta1_MachineDeploymentList_To_v1alpha4_MachineDeploymentList(in *v1beta1.MachineDeploymentList, out *MachineDeploymentList, s conversion.Scope) error {
 	out.ListMeta = in.ListMeta
-	out.Items = *(*[]MachineDeployment)(unsafe.Pointer(&in.Items))
+	if in.Items != nil {
+		in, out := &in.Items, &out.Items
+		*out = make([]MachineDeployment, len(*in))
+		for i := range *in {
+			if err := Convert_v1beta1_MachineDeployment_To_v1alpha4_MachineDeployment(&(*in)[i], &(*out)[i], s); err != nil {
+				return err
+			}
+		}
+	} else {
+		out.Items = nil
+	}
 	return nil
 }
 
@@ -1445,7 +1465,17 @@ func Convert_v1beta1_MachineSet_To_v1alpha4_MachineSet(in *v1beta1.MachineSet, o
 
 func autoConvert_v1alpha4_MachineSetList_To_v1beta1_MachineSetList(in *MachineSetList, out *v1beta1.MachineSetList, s conversion.Scope) error {
 	out.ListMeta = in.ListMeta
-	out.Items = *(*[]v1beta1.MachineSet)(unsafe.Pointer(&in.Items))
+	if in.Items != nil {
+		in, out := &in.Items, &out.Items
+		*out = make([]v1beta1.MachineSet, len(*in))
+		for i := range *in {
+			if err := Convert_v1alpha4_MachineSet_To_v1beta1_MachineSet(&(*in)[i], &(*out)[i], s); err != nil {
+				return err
+			}
+		}
+	} else {
+		out.Items = nil
+	}
 	return nil
 }
 
@@ -1456,7 +1486,17 @@ func Convert_v1alpha4_MachineSetList_To_v1beta1_MachineSetList(in *MachineSetLis
 
 func autoConvert_v1beta1_MachineSetList_To_v1alpha4_MachineSetList(in *v1beta1.MachineSetList, out *MachineSetList, s conversion.Scope) error {
 	out.ListMeta = in.ListMeta
-	out.Items = *(*[]MachineSet)(unsafe.Pointer(&in.Items))
+	if in.Items != nil {
+		in, out := &in.Items, &out.Items
+		*out = make([]MachineSet, len(*in))
+		for i := range *in {
+			if err := Convert_v1beta1_MachineSet_To_v1alpha4_MachineSet(&(*in)[i], &(*out)[i], s); err != nil {
+				return err
+			}
+		}
+	} else {
+		out.Items = nil
+	}
 	return nil
 }
 
@@ -1563,14 +1603,10 @@ func autoConvert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(in *v1beta1.Machine
 	out.ProviderID = (*string)(unsafe.Pointer(in.ProviderID))
 	out.FailureDomain = (*string)(unsafe.Pointer(in.FailureDomain))
 	out.NodeDrainTimeout = (*metav1.Duration)(unsafe.Pointer(in.NodeDrainTimeout))
+	// WARNING: in.NodeDeletionTimeout requires manual conversion: does not exist in peer-type
 	return nil
 }
 
-// Convert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec is an autogenerated conversion function.
-func Convert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(in *v1beta1.MachineSpec, out *MachineSpec, s conversion.Scope) error {
-	return autoConvert_v1beta1_MachineSpec_To_v1alpha4_MachineSpec(in, out, s)
-}
-
 func autoConvert_v1alpha4_MachineStatus_To_v1beta1_MachineStatus(in *MachineStatus, out *v1beta1.MachineStatus, s conversion.Scope) error {
 	out.NodeRef = (*v1.ObjectReference)(unsafe.Pointer(in.NodeRef))
 	out.NodeInfo = (*v1.NodeSystemInfo)(unsafe.Pointer(in.NodeInfo))
diff --git a/api/v1beta1/machine_types.go b/api/v1beta1/machine_types.go
index b50ce9fbaa3c..073610fa03bf 100644
--- a/api/v1beta1/machine_types.go
+++ b/api/v1beta1/machine_types.go
@@ -96,6 +96,12 @@ type MachineSpec struct {
 	// NOTE: NodeDrainTimeout is different from `kubectl drain --timeout`
 	// +optional
 	NodeDrainTimeout *metav1.Duration `json:"nodeDrainTimeout,omitempty"`
+
+	// NodeDeletionTimeout defines how long the controller will attempt to delete the Node that the Machine
+	// hosts after the Machine is marked for deletion. A duration of 0 will retry deletion indefinitely.
+	// Defaults to 10 seconds.
+	// +optional
+	NodeDeletionTimeout *metav1.Duration `json:"nodeDeletionTimeout,omitempty"`
 }
 
 // ANCHOR_END: MachineSpec
diff --git a/api/v1beta1/machine_webhook.go b/api/v1beta1/machine_webhook.go
index dd27f8300d53..ec7058c533eb 100644
--- a/api/v1beta1/machine_webhook.go
+++ b/api/v1beta1/machine_webhook.go
@@ -19,8 +19,10 @@ package v1beta1
 import (
 	"fmt"
 	"strings"
+	"time"
 
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/runtime"
 	"k8s.io/apimachinery/pkg/util/validation/field"
 	ctrl "sigs.k8s.io/controller-runtime"
@@ -29,6 +31,8 @@ import (
 	"sigs.k8s.io/cluster-api/util/version"
 )
 
+const defaultNodeDeletionTimeout = 10 * time.Second
+
 func (m *Machine) SetupWebhookWithManager(mgr ctrl.Manager) error {
 	return ctrl.NewWebhookManagedBy(mgr).
 		For(m).
@@ -60,6 +64,10 @@ func (m *Machine) Default() {
 		normalizedVersion := "v" + *m.Spec.Version
 		m.Spec.Version = &normalizedVersion
 	}
+
+	if m.Spec.NodeDeletionTimeout == nil {
+		m.Spec.NodeDeletionTimeout = &metav1.Duration{Duration: defaultNodeDeletionTimeout}
+	}
 }
 
 // ValidateCreate implements webhook.Validator so a webhook will be registered for the type.
diff --git a/api/v1beta1/machine_webhook_test.go b/api/v1beta1/machine_webhook_test.go
index 71383d43050b..0218ffa6f854 100644
--- a/api/v1beta1/machine_webhook_test.go
+++ b/api/v1beta1/machine_webhook_test.go
@@ -46,6 +46,7 @@ func TestMachineDefault(t *testing.T) {
 	g.Expect(m.Spec.Bootstrap.ConfigRef.Namespace).To(Equal(m.Namespace))
 	g.Expect(m.Spec.InfrastructureRef.Namespace).To(Equal(m.Namespace))
 	g.Expect(*m.Spec.Version).To(Equal("v1.17.5"))
+	g.Expect(m.Spec.NodeDeletionTimeout.Duration).To(Equal(defaultNodeDeletionTimeout))
 }
 
 func TestMachineBootstrapValidation(t *testing.T) {
diff --git a/api/v1beta1/zz_generated.deepcopy.go b/api/v1beta1/zz_generated.deepcopy.go
index 958ed279fb5f..686dd2cbbb64 100644
--- a/api/v1beta1/zz_generated.deepcopy.go
+++ b/api/v1beta1/zz_generated.deepcopy.go
@@ -1323,6 +1323,11 @@ func (in *MachineSpec) DeepCopyInto(out *MachineSpec) {
 		*out = new(metav1.Duration)
 		**out = **in
 	}
+	if in.NodeDeletionTimeout != nil {
+		in, out := &in.NodeDeletionTimeout, &out.NodeDeletionTimeout
+		*out = new(metav1.Duration)
+		**out = **in
+	}
 }
 
 // DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new MachineSpec.
diff --git a/config/crd/bases/cluster.x-k8s.io_machinedeployments.yaml b/config/crd/bases/cluster.x-k8s.io_machinedeployments.yaml
index 40d28f1fd07a..0bb0b9093921 100644
--- a/config/crd/bases/cluster.x-k8s.io_machinedeployments.yaml
+++ b/config/crd/bases/cluster.x-k8s.io_machinedeployments.yaml
@@ -1285,6 +1285,12 @@ spec:
                             description: 'UID of the referent. More info: https://kubernetes.io/docs/concepts/overview/working-with-objects/names/#uids'
                             type: string
                         type: object
+                      nodeDeletionTimeout:
+                        description: NodeDeletionTimeout defines how long the controller
+                          will attempt to delete the Node that the Machine hosts after
+                          the Machine is marked for deletion. A duration of 0 will
+                          retry deletion indefinitely. Defaults to 10 seconds.
+                        type: string
                       nodeDrainTimeout:
                         description: 'NodeDrainTimeout is the total amount of time
                           that the controller will spend on draining a node. The default
diff --git a/config/crd/bases/cluster.x-k8s.io_machinepools.yaml b/config/crd/bases/cluster.x-k8s.io_machinepools.yaml
index abc9350babbb..c4d81d8ea7db 100644
--- a/config/crd/bases/cluster.x-k8s.io_machinepools.yaml
+++ b/config/crd/bases/cluster.x-k8s.io_machinepools.yaml
@@ -1165,6 +1165,12 @@ spec:
                             description: 'UID of the referent. More info: https://kubernetes.io/docs/concepts/overview/working-with-objects/names/#uids'
                             type: string
                         type: object
+                      nodeDeletionTimeout:
+                        description: NodeDeletionTimeout defines how long the controller
+                          will attempt to delete the Node that the Machine hosts after
+                          the Machine is marked for deletion. A duration of 0 will
+                          retry deletion indefinitely. Defaults to 10 seconds.
+                        type: string
                       nodeDrainTimeout:
                         description: 'NodeDrainTimeout is the total amount of time
                           that the controller will spend on draining a node. The default
diff --git a/config/crd/bases/cluster.x-k8s.io_machines.yaml b/config/crd/bases/cluster.x-k8s.io_machines.yaml
index 40a2779948be..4665fba88ed4 100644
--- a/config/crd/bases/cluster.x-k8s.io_machines.yaml
+++ b/config/crd/bases/cluster.x-k8s.io_machines.yaml
@@ -886,6 +886,12 @@ spec:
                     description: 'UID of the referent. More info: https://kubernetes.io/docs/concepts/overview/working-with-objects/names/#uids'
                     type: string
                 type: object
+              nodeDeletionTimeout:
+                description: NodeDeletionTimeout defines how long the controller will
+                  attempt to delete the Node that the Machine hosts after the Machine
+                  is marked for deletion. A duration of 0 will retry deletion indefinitely.
+                  Defaults to 10 seconds.
+                type: string
               nodeDrainTimeout:
                 description: 'NodeDrainTimeout is the total amount of time that the
                   controller will spend on draining a node. The default value is 0,
diff --git a/config/crd/bases/cluster.x-k8s.io_machinesets.yaml b/config/crd/bases/cluster.x-k8s.io_machinesets.yaml
index 48cd9047a8b7..596563b9581d 100644
--- a/config/crd/bases/cluster.x-k8s.io_machinesets.yaml
+++ b/config/crd/bases/cluster.x-k8s.io_machinesets.yaml
@@ -1091,6 +1091,12 @@ spec:
                             description: 'UID of the referent. More info: https://kubernetes.io/docs/concepts/overview/working-with-objects/names/#uids'
                             type: string
                         type: object
+                      nodeDeletionTimeout:
+                        description: NodeDeletionTimeout defines how long the controller
+                          will attempt to delete the Node that the Machine hosts after
+                          the Machine is marked for deletion. A duration of 0 will
+                          retry deletion indefinitely. Defaults to 10 seconds.
+                        type: string
                       nodeDrainTimeout:
                         description: 'NodeDrainTimeout is the total amount of time
                           that the controller will spend on draining a node. The default
diff --git a/controlplane/kubeadm/api/v1alpha3/conversion.go b/controlplane/kubeadm/api/v1alpha3/conversion.go
index cd7c1913a743..124b8933b39a 100644
--- a/controlplane/kubeadm/api/v1alpha3/conversion.go
+++ b/controlplane/kubeadm/api/v1alpha3/conversion.go
@@ -39,6 +39,7 @@ func (src *KubeadmControlPlane) ConvertTo(dstRaw conversion.Hub) error {
 	}
 
 	dst.Spec.MachineTemplate.ObjectMeta = restored.Spec.MachineTemplate.ObjectMeta
+	dst.Spec.MachineTemplate.NodeDeletionTimeout = restored.Spec.MachineTemplate.NodeDeletionTimeout
 	dst.Status.Version = restored.Status.Version
 
 	if restored.Spec.KubeadmConfigSpec.JoinConfiguration != nil && restored.Spec.KubeadmConfigSpec.JoinConfiguration.NodeRegistration.IgnorePreflightErrors != nil {
diff --git a/controlplane/kubeadm/api/v1alpha4/conversion.go b/controlplane/kubeadm/api/v1alpha4/conversion.go
index 7147736f29d9..61eeec1a4fa5 100644
--- a/controlplane/kubeadm/api/v1alpha4/conversion.go
+++ b/controlplane/kubeadm/api/v1alpha4/conversion.go
@@ -46,6 +46,8 @@ func (src *KubeadmControlPlane) ConvertTo(dstRaw conversion.Hub) error {
 		dst.Spec.KubeadmConfigSpec.JoinConfiguration.Patches = restored.Spec.KubeadmConfigSpec.JoinConfiguration.Patches
 	}
 
+	dst.Spec.MachineTemplate.NodeDeletionTimeout = restored.Spec.MachineTemplate.NodeDeletionTimeout
+
 	return nil
 }
 
@@ -93,6 +95,11 @@ func (src *KubeadmControlPlaneTemplate) ConvertTo(dstRaw conversion.Hub) error {
 	if restored.Spec.Template.Spec.KubeadmConfigSpec.JoinConfiguration != nil {
 		dst.Spec.Template.Spec.KubeadmConfigSpec.JoinConfiguration.Patches = restored.Spec.Template.Spec.KubeadmConfigSpec.JoinConfiguration.Patches
 	}
+	if dst.Spec.Template.Spec.MachineTemplate == nil {
+		dst.Spec.Template.Spec.MachineTemplate = restored.Spec.Template.Spec.MachineTemplate
+	} else if restored.Spec.Template.Spec.MachineTemplate != nil {
+		dst.Spec.Template.Spec.MachineTemplate.NodeDeletionTimeout = restored.Spec.Template.Spec.MachineTemplate.NodeDeletionTimeout
+	}
 
 	return nil
 }
@@ -175,3 +182,8 @@ func Convert_v1beta1_KubeadmControlPlaneTemplateResourceSpec_To_v1alpha4_Kubeadm
 
 	return nil
 }
+
+func Convert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate(in *controlplanev1.KubeadmControlPlaneMachineTemplate, out *KubeadmControlPlaneMachineTemplate, s apiconversion.Scope) error {
+	// .NodeDrainTimeout was added in v1beta1.
+	return autoConvert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate(in, out, s)
+}
diff --git a/controlplane/kubeadm/api/v1alpha4/zz_generated.conversion.go b/controlplane/kubeadm/api/v1alpha4/zz_generated.conversion.go
index eec854984534..8e8241b7e5b4 100644
--- a/controlplane/kubeadm/api/v1alpha4/zz_generated.conversion.go
+++ b/controlplane/kubeadm/api/v1alpha4/zz_generated.conversion.go
@@ -67,11 +67,6 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
-	if err := s.AddGeneratedConversionFunc((*v1beta1.KubeadmControlPlaneMachineTemplate)(nil), (*KubeadmControlPlaneMachineTemplate)(nil), func(a, b interface{}, scope conversion.Scope) error {
-		return Convert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate(a.(*v1beta1.KubeadmControlPlaneMachineTemplate), b.(*KubeadmControlPlaneMachineTemplate), scope)
-	}); err != nil {
-		return err
-	}
 	if err := s.AddGeneratedConversionFunc((*KubeadmControlPlaneSpec)(nil), (*v1beta1.KubeadmControlPlaneSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1alpha4_KubeadmControlPlaneSpec_To_v1beta1_KubeadmControlPlaneSpec(a.(*KubeadmControlPlaneSpec), b.(*v1beta1.KubeadmControlPlaneSpec), scope)
 	}); err != nil {
@@ -157,6 +152,11 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
+	if err := s.AddConversionFunc((*v1beta1.KubeadmControlPlaneMachineTemplate)(nil), (*KubeadmControlPlaneMachineTemplate)(nil), func(a, b interface{}, scope conversion.Scope) error {
+		return Convert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate(a.(*v1beta1.KubeadmControlPlaneMachineTemplate), b.(*KubeadmControlPlaneMachineTemplate), scope)
+	}); err != nil {
+		return err
+	}
 	if err := s.AddConversionFunc((*v1beta1.KubeadmControlPlaneTemplateResourceSpec)(nil), (*KubeadmControlPlaneSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1beta1_KubeadmControlPlaneTemplateResourceSpec_To_v1alpha4_KubeadmControlPlaneSpec(a.(*v1beta1.KubeadmControlPlaneTemplateResourceSpec), b.(*KubeadmControlPlaneSpec), scope)
 	}); err != nil {
@@ -259,14 +259,10 @@ func autoConvert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmC
 	}
 	out.InfrastructureRef = in.InfrastructureRef
 	out.NodeDrainTimeout = (*v1.Duration)(unsafe.Pointer(in.NodeDrainTimeout))
+	// WARNING: in.NodeDeletionTimeout requires manual conversion: does not exist in peer-type
 	return nil
 }
 
-// Convert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate is an autogenerated conversion function.
-func Convert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate(in *v1beta1.KubeadmControlPlaneMachineTemplate, out *KubeadmControlPlaneMachineTemplate, s conversion.Scope) error {
-	return autoConvert_v1beta1_KubeadmControlPlaneMachineTemplate_To_v1alpha4_KubeadmControlPlaneMachineTemplate(in, out, s)
-}
-
 func autoConvert_v1alpha4_KubeadmControlPlaneSpec_To_v1beta1_KubeadmControlPlaneSpec(in *KubeadmControlPlaneSpec, out *v1beta1.KubeadmControlPlaneSpec, s conversion.Scope) error {
 	out.Replicas = (*int32)(unsafe.Pointer(in.Replicas))
 	out.Version = in.Version
diff --git a/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_types.go b/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_types.go
index e7e41c19136f..46d81813ea8f 100644
--- a/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_types.go
+++ b/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_types.go
@@ -101,6 +101,12 @@ type KubeadmControlPlaneMachineTemplate struct {
 	// NOTE: NodeDrainTimeout is different from `kubectl drain --timeout`
 	// +optional
 	NodeDrainTimeout *metav1.Duration `json:"nodeDrainTimeout,omitempty"`
+
+	// NodeDeletionTimeout defines how long the machine controller will attempt to delete the Node that the Machine
+	// hosts after the Machine is marked for deletion. A duration of 0 will retry deletion indefinitely.
+	// If no value is provided, the default value for this property of the Machine resource will be used.
+	// +optional
+	NodeDeletionTimeout *metav1.Duration `json:"nodeDeletionTimeout,omitempty"`
 }
 
 // RolloutStrategy describes how to replace existing machines
diff --git a/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook.go b/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook.go
index 896ef5d0e36c..4a7543a0e67f 100644
--- a/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook.go
+++ b/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook.go
@@ -152,6 +152,7 @@ func (in *KubeadmControlPlane) ValidateUpdate(old runtime.Object) error {
 		{spec, "machineTemplate", "infrastructureRef", "apiVersion"},
 		{spec, "machineTemplate", "infrastructureRef", "name"},
 		{spec, "machineTemplate", "nodeDrainTimeout"},
+		{spec, "machineTemplate", "nodeDeletionTimeout"},
 		{spec, "replicas"},
 		{spec, "version"},
 		{spec, "rolloutAfter"},
diff --git a/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook_test.go b/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook_test.go
index 9923c95274b9..19d23538fccc 100644
--- a/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook_test.go
+++ b/controlplane/kubeadm/api/v1beta1/kubeadm_control_plane_webhook_test.go
@@ -239,7 +239,8 @@ func TestKubeadmControlPlaneValidateUpdate(t *testing.T) {
 					Namespace:  "foo",
 					Name:       "infraTemplate",
 				},
-				NodeDrainTimeout: &metav1.Duration{Duration: time.Second},
+				NodeDrainTimeout:    &metav1.Duration{Duration: time.Second},
+				NodeDeletionTimeout: &metav1.Duration{Duration: time.Second},
 			},
 			Replicas: pointer.Int32Ptr(1),
 			RolloutStrategy: &RolloutStrategy{
@@ -365,6 +366,7 @@ func TestKubeadmControlPlaneValidateUpdate(t *testing.T) {
 	validUpdate.Spec.MachineTemplate.InfrastructureRef.APIVersion = "test/v1alpha2"
 	validUpdate.Spec.MachineTemplate.InfrastructureRef.Name = "orange"
 	validUpdate.Spec.MachineTemplate.NodeDrainTimeout = &metav1.Duration{Duration: 10 * time.Second}
+	validUpdate.Spec.MachineTemplate.NodeDeletionTimeout = &metav1.Duration{Duration: 10 * time.Second}
 	validUpdate.Spec.Replicas = pointer.Int32Ptr(5)
 	now := metav1.NewTime(time.Now())
 	validUpdate.Spec.RolloutAfter = &now
diff --git a/controlplane/kubeadm/api/v1beta1/kubeadmcontrolplanetemplate_types.go b/controlplane/kubeadm/api/v1beta1/kubeadmcontrolplanetemplate_types.go
index e5e3e15f2862..575b6b8e0771 100644
--- a/controlplane/kubeadm/api/v1beta1/kubeadmcontrolplanetemplate_types.go
+++ b/controlplane/kubeadm/api/v1beta1/kubeadmcontrolplanetemplate_types.go
@@ -99,4 +99,10 @@ type KubeadmControlPlaneTemplateMachineTemplate struct {
 	// NOTE: NodeDrainTimeout is different from `kubectl drain --timeout`
 	// +optional
 	NodeDrainTimeout *metav1.Duration `json:"nodeDrainTimeout,omitempty"`
+
+	// NodeDeletionTimeout defines how long the machine controller will attempt to delete the Node that the Machine
+	// hosts after the Machine is marked for deletion. A duration of 0 will retry deletion indefinitely.
+	// If no value is provided, the default value for this property of the Machine resource will be used.
+	// +optional
+	NodeDeletionTimeout *metav1.Duration `json:"nodeDeletionTimeout,omitempty"`
 }
diff --git a/controlplane/kubeadm/api/v1beta1/zz_generated.deepcopy.go b/controlplane/kubeadm/api/v1beta1/zz_generated.deepcopy.go
index 15fac74acc5d..ff16517906e7 100644
--- a/controlplane/kubeadm/api/v1beta1/zz_generated.deepcopy.go
+++ b/controlplane/kubeadm/api/v1beta1/zz_generated.deepcopy.go
@@ -97,6 +97,11 @@ func (in *KubeadmControlPlaneMachineTemplate) DeepCopyInto(out *KubeadmControlPl
 		*out = new(v1.Duration)
 		**out = **in
 	}
+	if in.NodeDeletionTimeout != nil {
+		in, out := &in.NodeDeletionTimeout, &out.NodeDeletionTimeout
+		*out = new(v1.Duration)
+		**out = **in
+	}
 }
 
 // DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new KubeadmControlPlaneMachineTemplate.
@@ -238,6 +243,11 @@ func (in *KubeadmControlPlaneTemplateMachineTemplate) DeepCopyInto(out *KubeadmC
 		*out = new(v1.Duration)
 		**out = **in
 	}
+	if in.NodeDeletionTimeout != nil {
+		in, out := &in.NodeDeletionTimeout, &out.NodeDeletionTimeout
+		*out = new(v1.Duration)
+		**out = **in
+	}
 }
 
 // DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new KubeadmControlPlaneTemplateMachineTemplate.
diff --git a/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanes.yaml b/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanes.yaml
index bdd6b0cef72e..9a5a779a5183 100644
--- a/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanes.yaml
+++ b/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanes.yaml
@@ -3510,6 +3510,14 @@ spec:
                           More info: http://kubernetes.io/docs/user-guide/labels'
                         type: object
                     type: object
+                  nodeDeletionTimeout:
+                    description: NodeDeletionTimeout defines how long the machine
+                      controller will attempt to delete the Node that the Machine
+                      hosts after the Machine is marked for deletion. A duration of
+                      0 will retry deletion indefinitely. If no value is provided,
+                      the default value for this property of the Machine resource
+                      will be used.
+                    type: string
                   nodeDrainTimeout:
                     description: 'NodeDrainTimeout is the total amount of time that
                       the controller will spend on draining a controlplane node The
diff --git a/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanetemplates.yaml b/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanetemplates.yaml
index fabde6b0f911..eaf234e59b9d 100644
--- a/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanetemplates.yaml
+++ b/controlplane/kubeadm/config/crd/bases/controlplane.cluster.x-k8s.io_kubeadmcontrolplanetemplates.yaml
@@ -2277,6 +2277,14 @@ spec:
                           machines should be shaped when creating or updating a control
                           plane.
                         properties:
+                          nodeDeletionTimeout:
+                            description: NodeDeletionTimeout defines how long the
+                              machine controller will attempt to delete the Node that
+                              the Machine hosts after the Machine is marked for deletion.
+                              A duration of 0 will retry deletion indefinitely. If
+                              no value is provided, the default value for this property
+                              of the Machine resource will be used.
+                            type: string
                           nodeDrainTimeout:
                             description: 'NodeDrainTimeout is the total amount of
                               time that the controller will spend on draining a controlplane
diff --git a/controlplane/kubeadm/internal/controllers/helpers.go b/controlplane/kubeadm/internal/controllers/helpers.go
index be9fa5a70af3..31034141ca9f 100644
--- a/controlplane/kubeadm/internal/controllers/helpers.go
+++ b/controlplane/kubeadm/internal/controllers/helpers.go
@@ -289,6 +289,9 @@ func (r *KubeadmControlPlaneReconciler) generateMachine(ctx context.Context, kcp
 			NodeDrainTimeout: kcp.Spec.MachineTemplate.NodeDrainTimeout,
 		},
 	}
+	if kcp.Spec.MachineTemplate.NodeDeletionTimeout != nil {
+		machine.Spec.NodeDeletionTimeout = kcp.Spec.MachineTemplate.NodeDeletionTimeout
+	}
 
 	// Machine's bootstrap config may be missing ClusterConfiguration if it is not the first machine in the control plane.
 	// We store ClusterConfiguration as annotation here to detect any changes in KCP ClusterConfiguration and rollout the machine if any.
diff --git a/docs/book/src/developer/architecture/controllers/control-plane.md b/docs/book/src/developer/architecture/controllers/control-plane.md
index 5525561c4857..ffc70ccb80e6 100644
--- a/docs/book/src/developer/architecture/controllers/control-plane.md
+++ b/docs/book/src/developer/architecture/controllers/control-plane.md
@@ -97,7 +97,12 @@ documentation][scale].
 * `machineTemplate.nodeDrainTimeout` - is a *metav1.Duration defining the total amount of time
   that the controller will spend on draining a control plane node.
   The default value is 0, meaning that the node can be drained without any time limitations.
-  
+
+* `machineTemplate.nodeDeletionTimeout` - is a *metav1.Duration defining how long the controller
+  will attempt to delete the Node that is hosted by a Machine after the Machine is marked for
+  deletion. A duration of 0 will retry deletion indefinitely. It defaults to 10 seconds on the
+  Machine.
+
 #### Required `status` fields
 
 The `ImplementationControlPlane` object **must** have a `status` object.
diff --git a/exp/api/v1alpha3/conversion.go b/exp/api/v1alpha3/conversion.go
index 47cedb064ccf..a06e3994d6a9 100644
--- a/exp/api/v1alpha3/conversion.go
+++ b/exp/api/v1alpha3/conversion.go
@@ -22,6 +22,7 @@ import (
 	"sigs.k8s.io/controller-runtime/pkg/conversion"
 
 	expv1 "sigs.k8s.io/cluster-api/exp/api/v1beta1"
+	utilconversion "sigs.k8s.io/cluster-api/util/conversion"
 )
 
 // Convert_v1alpha3_MachinePoolSpec_To_v1beta1_MachinePoolSpec is an autogenerated conversion function.
@@ -60,13 +61,27 @@ func Convert_v1beta1_MachinePool_To_v1alpha3_MachinePool(in *expv1.MachinePool,
 func (src *MachinePool) ConvertTo(dstRaw conversion.Hub) error {
 	dst := dstRaw.(*expv1.MachinePool)
 
-	return Convert_v1alpha3_MachinePool_To_v1beta1_MachinePool(src, dst, nil)
+	if err := Convert_v1alpha3_MachinePool_To_v1beta1_MachinePool(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Manually restore data.
+	restored := &expv1.MachinePool{}
+	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
+		return err
+	}
+	dst.Spec.Template.Spec.NodeDeletionTimeout = restored.Spec.Template.Spec.NodeDeletionTimeout
+	return nil
 }
 
 func (dst *MachinePool) ConvertFrom(srcRaw conversion.Hub) error {
 	src := srcRaw.(*expv1.MachinePool)
 
-	return Convert_v1beta1_MachinePool_To_v1alpha3_MachinePool(src, dst, nil)
+	if err := Convert_v1beta1_MachinePool_To_v1alpha3_MachinePool(src, dst, nil); err != nil {
+		return err
+	}
+
+	return utilconversion.MarshalData(src, dst)
 }
 
 func (src *MachinePoolList) ConvertTo(dstRaw conversion.Hub) error {
diff --git a/exp/api/v1alpha4/conversion.go b/exp/api/v1alpha4/conversion.go
index 609d15cff4b5..a9408d3cf6af 100644
--- a/exp/api/v1alpha4/conversion.go
+++ b/exp/api/v1alpha4/conversion.go
@@ -20,18 +20,32 @@ import (
 	"sigs.k8s.io/controller-runtime/pkg/conversion"
 
 	expv1 "sigs.k8s.io/cluster-api/exp/api/v1beta1"
+	utilconversion "sigs.k8s.io/cluster-api/util/conversion"
 )
 
 func (src *MachinePool) ConvertTo(dstRaw conversion.Hub) error {
 	dst := dstRaw.(*expv1.MachinePool)
 
-	return Convert_v1alpha4_MachinePool_To_v1beta1_MachinePool(src, dst, nil)
+	if err := Convert_v1alpha4_MachinePool_To_v1beta1_MachinePool(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Manually restore data.
+	restored := &expv1.MachinePool{}
+	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
+		return err
+	}
+	dst.Spec.Template.Spec.NodeDeletionTimeout = restored.Spec.Template.Spec.NodeDeletionTimeout
+	return nil
 }
 
 func (dst *MachinePool) ConvertFrom(srcRaw conversion.Hub) error {
 	src := srcRaw.(*expv1.MachinePool)
 
-	return Convert_v1beta1_MachinePool_To_v1alpha4_MachinePool(src, dst, nil)
+	if err := Convert_v1beta1_MachinePool_To_v1alpha4_MachinePool(src, dst, nil); err != nil {
+		return err
+	}
+	return utilconversion.MarshalData(src, dst)
 }
 
 func (src *MachinePoolList) ConvertTo(dstRaw conversion.Hub) error {
diff --git a/internal/controllers/machine/machine_controller.go b/internal/controllers/machine/machine_controller.go
index 4ff747c76e90..9da2cd58c854 100644
--- a/internal/controllers/machine/machine_controller.go
+++ b/internal/controllers/machine/machine_controller.go
@@ -86,6 +86,10 @@ type Reconciler struct {
 	controller      controller.Controller
 	recorder        record.EventRecorder
 	externalTracker external.ObjectTracker
+
+	// nodeDeletionRetryTimeout determines how long the controller will retry deleting a node
+	// during a single reconciliation.
+	nodeDeletionRetryTimeout time.Duration
 }
 
 func (r *Reconciler) SetupWithManager(ctx context.Context, mgr ctrl.Manager, options controller.Options) error {
@@ -94,6 +98,10 @@ func (r *Reconciler) SetupWithManager(ctx context.Context, mgr ctrl.Manager, opt
 		return err
 	}
 
+	if r.nodeDeletionRetryTimeout.Nanoseconds() == 0 {
+		r.nodeDeletionRetryTimeout = 10 * time.Second
+	}
+
 	controller, err := ctrl.NewControllerManagedBy(mgr).
 		For(&clusterv1.Machine{}).
 		WithOptions(options).
@@ -380,16 +388,22 @@ func (r *Reconciler) reconcileDelete(ctx context.Context, cluster *clusterv1.Clu
 		log.Info("Deleting node", "node", m.Status.NodeRef.Name)
 
 		var deleteNodeErr error
-		waitErr := wait.PollImmediate(2*time.Second, 10*time.Second, func() (bool, error) {
+		waitErr := wait.PollImmediate(2*time.Second, r.nodeDeletionRetryTimeout, func() (bool, error) {
 			if deleteNodeErr = r.deleteNode(ctx, cluster, m.Status.NodeRef.Name); deleteNodeErr != nil && !apierrors.IsNotFound(errors.Cause(deleteNodeErr)) {
 				return false, nil
 			}
 			return true, nil
 		})
 		if waitErr != nil {
-			log.Error(deleteNodeErr, "Timed out deleting node, moving on", "node", m.Status.NodeRef.Name)
+			log.Error(deleteNodeErr, "Timed out deleting node", "node", m.Status.NodeRef.Name)
 			conditions.MarkFalse(m, clusterv1.MachineNodeHealthyCondition, clusterv1.DeletionFailedReason, clusterv1.ConditionSeverityWarning, "")
 			r.recorder.Eventf(m, corev1.EventTypeWarning, "FailedDeleteNode", "error deleting Machine's node: %v", deleteNodeErr)
+
+			// If the node deletion timeout is not expired yet, requeue the Machine for reconciliation.
+			if m.Spec.NodeDeletionTimeout == nil || m.Spec.NodeDeletionTimeout.Nanoseconds() == 0 || m.DeletionTimestamp.Add(m.Spec.NodeDeletionTimeout.Duration).After(time.Now()) {
+				return ctrl.Result{}, deleteNodeErr
+			}
+			log.Info("Node deletion timeout expired, continuing without Node deletion.")
 		}
 	}
 
diff --git a/internal/controllers/machine/machine_controller_test.go b/internal/controllers/machine/machine_controller_test.go
index 3d9f7c38a729..ae494f459ac8 100644
--- a/internal/controllers/machine/machine_controller_test.go
+++ b/internal/controllers/machine/machine_controller_test.go
@@ -17,6 +17,8 @@ limitations under the License.
 package machine
 
 import (
+	"context"
+	"fmt"
 	"testing"
 	"time"
 
@@ -27,9 +29,11 @@ import (
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/apis/meta/v1/unstructured"
 	"k8s.io/client-go/kubernetes/scheme"
+	"k8s.io/client-go/tools/record"
 	"k8s.io/utils/pointer"
 	ctrl "sigs.k8s.io/controller-runtime"
 	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/client/apiutil"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
 	"sigs.k8s.io/controller-runtime/pkg/log"
 	"sigs.k8s.io/controller-runtime/pkg/reconcile"
@@ -1856,6 +1860,193 @@ func TestNodeToMachine(t *testing.T) {
 	}
 }
 
+type fakeClientWithNodeDeletionErr struct {
+	client.Client
+}
+
+func (fc fakeClientWithNodeDeletionErr) Delete(ctx context.Context, obj client.Object, opts ...client.DeleteOption) error {
+	gvk, err := apiutil.GVKForObject(obj, fakeScheme)
+	if err == nil && gvk.Kind == "Node" {
+		return fmt.Errorf("fake error")
+	}
+	return fc.Client.Delete(ctx, obj, opts...)
+}
+
+func TestNodeDeletion(t *testing.T) {
+	g := NewWithT(t)
+
+	deletionTime := metav1.Now().Add(-1 * time.Second)
+
+	testCluster := clusterv1.Cluster{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test-cluster",
+			Namespace: metav1.NamespaceDefault,
+		},
+	}
+
+	node := &corev1.Node{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: "test",
+		},
+		Spec: corev1.NodeSpec{ProviderID: "test://id-1"},
+	}
+
+	testMachine := clusterv1.Machine{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test",
+			Namespace: metav1.NamespaceDefault,
+			Labels: map[string]string{
+				clusterv1.MachineControlPlaneLabelName: "",
+			},
+			Annotations: map[string]string{
+				"machine.cluster.x-k8s.io/exclude-node-draining": "",
+			},
+			Finalizers:        []string{clusterv1.MachineFinalizer},
+			DeletionTimestamp: &metav1.Time{Time: deletionTime},
+		},
+		Spec: clusterv1.MachineSpec{
+			ClusterName: "test-cluster",
+			InfrastructureRef: corev1.ObjectReference{
+				APIVersion: "infrastructure.cluster.x-k8s.io/v1beta1",
+				Kind:       "GenericInfrastructureMachine",
+				Name:       "infra-config1",
+			},
+			Bootstrap: clusterv1.Bootstrap{DataSecretName: pointer.StringPtr("data")},
+		},
+		Status: clusterv1.MachineStatus{
+			NodeRef: &corev1.ObjectReference{
+				Name: "test",
+			},
+		},
+	}
+
+	cpmachine1 := &clusterv1.Machine{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "cp1",
+			Namespace: metav1.NamespaceDefault,
+			Labels: map[string]string{
+				clusterv1.ClusterLabelName:             "test-cluster",
+				clusterv1.MachineControlPlaneLabelName: "",
+			},
+			Finalizers: []string{clusterv1.MachineFinalizer},
+		},
+		Spec: clusterv1.MachineSpec{
+			ClusterName:       "test-cluster",
+			InfrastructureRef: corev1.ObjectReference{},
+			Bootstrap:         clusterv1.Bootstrap{DataSecretName: pointer.StringPtr("data")},
+		},
+		Status: clusterv1.MachineStatus{
+			NodeRef: &corev1.ObjectReference{
+				Name: "cp1",
+			},
+		},
+	}
+
+	testCases := []struct {
+		name               string
+		deletionTimeout    *metav1.Duration
+		resultErr          bool
+		clusterDeleted     bool
+		expectNodeDeletion bool
+		createFakeClient   func(...client.Object) client.Client
+	}{
+		{
+			name:               "should return no error when deletion is successful",
+			deletionTimeout:    &metav1.Duration{Duration: time.Second},
+			resultErr:          false,
+			expectNodeDeletion: true,
+			createFakeClient: func(initObjs ...client.Object) client.Client {
+				return fake.NewClientBuilder().
+					WithObjects(initObjs...).
+					Build()
+			},
+		},
+		{
+			name:               "should return an error when timeout is not expired and node deletion fails",
+			deletionTimeout:    &metav1.Duration{Duration: time.Hour},
+			resultErr:          true,
+			expectNodeDeletion: false,
+			createFakeClient: func(initObjs ...client.Object) client.Client {
+				fc := fake.NewClientBuilder().
+					WithObjects(initObjs...).
+					Build()
+				return fakeClientWithNodeDeletionErr{fc}
+			},
+		},
+		{
+			name:               "should return an error when timeout is infinite and node deletion fails",
+			deletionTimeout:    &metav1.Duration{Duration: 0}, // should lead to infinite timeout
+			resultErr:          true,
+			expectNodeDeletion: false,
+			createFakeClient: func(initObjs ...client.Object) client.Client {
+				fc := fake.NewClientBuilder().
+					WithObjects(initObjs...).
+					Build()
+				return fakeClientWithNodeDeletionErr{fc}
+			},
+		},
+		{
+			name:               "should not return an error when timeout is expired and node deletion fails",
+			deletionTimeout:    &metav1.Duration{Duration: time.Millisecond},
+			resultErr:          false,
+			expectNodeDeletion: false,
+			createFakeClient: func(initObjs ...client.Object) client.Client {
+				fc := fake.NewClientBuilder().
+					WithObjects(initObjs...).
+					Build()
+				return fakeClientWithNodeDeletionErr{fc}
+			},
+		},
+		{
+			name:               "should not delete the node or return an error when the cluster is marked for deletion",
+			deletionTimeout:    nil, // should lead to infinite timeout
+			resultErr:          false,
+			clusterDeleted:     true,
+			expectNodeDeletion: false,
+			createFakeClient: func(initObjs ...client.Object) client.Client {
+				fc := fake.NewClientBuilder().
+					WithObjects(initObjs...).
+					Build()
+				return fakeClientWithNodeDeletionErr{fc}
+			},
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			m := testMachine.DeepCopy()
+			m.Spec.NodeDeletionTimeout = tc.deletionTimeout
+
+			fakeClient := tc.createFakeClient(node, m, cpmachine1)
+			tracker := remote.NewTestClusterCacheTracker(ctrl.Log, fakeClient, fakeScheme, client.ObjectKeyFromObject(&testCluster))
+
+			r := &Reconciler{
+				Client:                   fakeClient,
+				Tracker:                  tracker,
+				recorder:                 record.NewFakeRecorder(10),
+				nodeDeletionRetryTimeout: 10 * time.Millisecond,
+			}
+
+			cluster := testCluster.DeepCopy()
+			if tc.clusterDeleted {
+				cluster.DeletionTimestamp = &metav1.Time{Time: deletionTime.Add(time.Hour)}
+			}
+
+			_, err := r.reconcileDelete(context.Background(), cluster, m)
+
+			if tc.resultErr {
+				g.Expect(err).To(HaveOccurred())
+			} else {
+				g.Expect(err).NotTo(HaveOccurred())
+				if tc.expectNodeDeletion {
+					n := &corev1.Node{}
+					g.Expect(fakeClient.Get(context.Background(), client.ObjectKeyFromObject(node), n)).NotTo(Succeed())
+				}
+			}
+		})
+	}
+}
+
 // adds a condition list to an external object.
 func addConditionsToExternal(u *unstructured.Unstructured, newConditions clusterv1.Conditions) {
 	existingConditions := clusterv1.Conditions{}