diff --git a/test/infrastructure/docker/api/v1alpha4/conversion.go b/test/infrastructure/docker/api/v1alpha4/conversion.go
index e8c9ae8d8236..6c7dc8507cd9 100644
--- a/test/infrastructure/docker/api/v1alpha4/conversion.go
+++ b/test/infrastructure/docker/api/v1alpha4/conversion.go
@@ -122,13 +122,35 @@ func (dst *DockerClusterTemplateList) ConvertFrom(srcRaw conversion.Hub) error {
 func (src *DockerMachine) ConvertTo(dstRaw conversion.Hub) error {
 	dst := dstRaw.(*infrav1.DockerMachine)
 
-	return Convert_v1alpha4_DockerMachine_To_v1beta1_DockerMachine(src, dst, nil)
+	if err := Convert_v1alpha4_DockerMachine_To_v1beta1_DockerMachine(src, dst, nil); err != nil {
+		return err
+	}
+
+	// Manually restore data.
+	restored := &infrav1.DockerMachine{}
+	if ok, err := utilconversion.UnmarshalData(src, restored); err != nil || !ok {
+		return err
+	}
+
+	if restored.Spec.BootstrapTimeout != nil {
+		dst.Spec.BootstrapTimeout = restored.Spec.BootstrapTimeout
+	}
+
+	return nil
 }
 
 func (dst *DockerMachine) ConvertFrom(srcRaw conversion.Hub) error {
 	src := srcRaw.(*infrav1.DockerMachine)
 
-	return Convert_v1beta1_DockerMachine_To_v1alpha4_DockerMachine(src, dst, nil)
+	if err := Convert_v1beta1_DockerMachine_To_v1alpha4_DockerMachine(src, dst, nil); err != nil {
+		return err
+	}
+
+	if err := utilconversion.MarshalData(src, dst); err != nil {
+		return err
+	}
+
+	return nil
 }
 
 func (src *DockerMachineList) ConvertTo(dstRaw conversion.Hub) error {
@@ -157,6 +179,7 @@ func (src *DockerMachineTemplate) ConvertTo(dstRaw conversion.Hub) error {
 	}
 
 	dst.Spec.Template.ObjectMeta = restored.Spec.Template.ObjectMeta
+	dst.Spec.Template.Spec.BootstrapTimeout = restored.Spec.Template.Spec.BootstrapTimeout
 
 	return nil
 }
@@ -201,3 +224,7 @@ func Convert_v1beta1_DockerMachineTemplateResource_To_v1alpha4_DockerMachineTemp
 func Convert_v1beta1_DockerLoadBalancer_To_v1alpha4_DockerLoadBalancer(in *infrav1.DockerLoadBalancer, out *DockerLoadBalancer, s apiconversion.Scope) error {
 	return autoConvert_v1beta1_DockerLoadBalancer_To_v1alpha4_DockerLoadBalancer(in, out, s)
 }
+
+func Convert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(in *infrav1.DockerMachineSpec, out *DockerMachineSpec, s apiconversion.Scope) error {
+	return autoConvert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(in, out, s)
+}
diff --git a/test/infrastructure/docker/api/v1alpha4/zz_generated.conversion.go b/test/infrastructure/docker/api/v1alpha4/zz_generated.conversion.go
index 71075f02d170..960ed662f0f9 100644
--- a/test/infrastructure/docker/api/v1alpha4/zz_generated.conversion.go
+++ b/test/infrastructure/docker/api/v1alpha4/zz_generated.conversion.go
@@ -153,11 +153,6 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
-	if err := s.AddGeneratedConversionFunc((*v1beta1.DockerMachineSpec)(nil), (*DockerMachineSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
-		return Convert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(a.(*v1beta1.DockerMachineSpec), b.(*DockerMachineSpec), scope)
-	}); err != nil {
-		return err
-	}
 	if err := s.AddGeneratedConversionFunc((*DockerMachineStatus)(nil), (*v1beta1.DockerMachineStatus)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1alpha4_DockerMachineStatus_To_v1beta1_DockerMachineStatus(a.(*DockerMachineStatus), b.(*v1beta1.DockerMachineStatus), scope)
 	}); err != nil {
@@ -233,6 +228,11 @@ func RegisterConversions(s *runtime.Scheme) error {
 	}); err != nil {
 		return err
 	}
+	if err := s.AddConversionFunc((*v1beta1.DockerMachineSpec)(nil), (*DockerMachineSpec)(nil), func(a, b interface{}, scope conversion.Scope) error {
+		return Convert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(a.(*v1beta1.DockerMachineSpec), b.(*DockerMachineSpec), scope)
+	}); err != nil {
+		return err
+	}
 	if err := s.AddConversionFunc((*v1beta1.DockerMachineTemplateResource)(nil), (*DockerMachineTemplateResource)(nil), func(a, b interface{}, scope conversion.Scope) error {
 		return Convert_v1beta1_DockerMachineTemplateResource_To_v1alpha4_DockerMachineTemplateResource(a.(*v1beta1.DockerMachineTemplateResource), b.(*DockerMachineTemplateResource), scope)
 	}); err != nil {
@@ -687,14 +687,10 @@ func autoConvert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(in *v1b
 	out.PreLoadImages = *(*[]string)(unsafe.Pointer(&in.PreLoadImages))
 	out.ExtraMounts = *(*[]Mount)(unsafe.Pointer(&in.ExtraMounts))
 	out.Bootstrapped = in.Bootstrapped
+	// WARNING: in.BootstrapTimeout requires manual conversion: does not exist in peer-type
 	return nil
 }
 
-// Convert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec is an autogenerated conversion function.
-func Convert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(in *v1beta1.DockerMachineSpec, out *DockerMachineSpec, s conversion.Scope) error {
-	return autoConvert_v1beta1_DockerMachineSpec_To_v1alpha4_DockerMachineSpec(in, out, s)
-}
-
 func autoConvert_v1alpha4_DockerMachineStatus_To_v1beta1_DockerMachineStatus(in *DockerMachineStatus, out *v1beta1.DockerMachineStatus, s conversion.Scope) error {
 	out.Ready = in.Ready
 	out.LoadBalancerConfigured = in.LoadBalancerConfigured
diff --git a/test/infrastructure/docker/api/v1beta1/dockermachine_types.go b/test/infrastructure/docker/api/v1beta1/dockermachine_types.go
index 7fbba3276f75..520b09a1d054 100644
--- a/test/infrastructure/docker/api/v1beta1/dockermachine_types.go
+++ b/test/infrastructure/docker/api/v1beta1/dockermachine_types.go
@@ -56,6 +56,11 @@ type DockerMachineSpec struct {
 	// When removing also remove from staticcheck exclude-rules for SA1019 in golangci.yml.
 	// +optional
 	Bootstrapped bool `json:"bootstrapped,omitempty"`
+
+	// BootstrapTimeout is the total time (in minutes) to wait for the machine to bootstrap before timing out.
+	// Defaults to 3 minutes if not set.
+	// +optional
+	BootstrapTimeout *metav1.Duration `json:"bootstrapTimeout,omitempty"`
 }
 
 // Mount specifies a host volume to mount into a container.
diff --git a/test/infrastructure/docker/api/v1beta1/zz_generated.deepcopy.go b/test/infrastructure/docker/api/v1beta1/zz_generated.deepcopy.go
index 6ae7a8e473dd..0b6a6efa9f41 100644
--- a/test/infrastructure/docker/api/v1beta1/zz_generated.deepcopy.go
+++ b/test/infrastructure/docker/api/v1beta1/zz_generated.deepcopy.go
@@ -22,6 +22,7 @@ package v1beta1
 
 import (
 	"k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/runtime"
 	apiv1beta1 "sigs.k8s.io/cluster-api/api/v1beta1"
 )
@@ -342,6 +343,11 @@ func (in *DockerMachineSpec) DeepCopyInto(out *DockerMachineSpec) {
 		*out = make([]Mount, len(*in))
 		copy(*out, *in)
 	}
+	if in.BootstrapTimeout != nil {
+		in, out := &in.BootstrapTimeout, &out.BootstrapTimeout
+		*out = new(metav1.Duration)
+		**out = **in
+	}
 }
 
 // DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new DockerMachineSpec.
diff --git a/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachines.yaml b/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachines.yaml
index ab73711b202f..dd77a2a81cd0 100644
--- a/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachines.yaml
+++ b/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachines.yaml
@@ -205,6 +205,11 @@ spec:
           spec:
             description: DockerMachineSpec defines the desired state of DockerMachine.
             properties:
+              bootstrapTimeout:
+                description: BootstrapTimeout is the total time (in minutes) to wait
+                  for the machine to bootstrap before timing out. Defaults to 3 minutes
+                  if not set.
+                type: string
               bootstrapped:
                 description: "Bootstrapped is true when the kubeadm bootstrapping
                   has been run against this machine \n Deprecated: This field will
diff --git a/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachinetemplates.yaml b/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachinetemplates.yaml
index 29ad60adffea..bdf4173a5692 100644
--- a/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachinetemplates.yaml
+++ b/test/infrastructure/docker/config/crd/bases/infrastructure.cluster.x-k8s.io_dockermachinetemplates.yaml
@@ -159,6 +159,11 @@ spec:
                     description: Spec is the specification of the desired behavior
                       of the machine.
                     properties:
+                      bootstrapTimeout:
+                        description: BootstrapTimeout is the total time (in minutes)
+                          to wait for the machine to bootstrap before timing out.
+                          Defaults to 3 minutes if not set.
+                        type: string
                       bootstrapped:
                         description: "Bootstrapped is true when the kubeadm bootstrapping
                           has been run against this machine \n Deprecated: This field
diff --git a/test/infrastructure/docker/internal/controllers/dockermachine_controller.go b/test/infrastructure/docker/internal/controllers/dockermachine_controller.go
index f2bfad8abbe7..8b517275acfa 100644
--- a/test/infrastructure/docker/internal/controllers/dockermachine_controller.go
+++ b/test/infrastructure/docker/internal/controllers/dockermachine_controller.go
@@ -25,6 +25,7 @@ import (
 	"github.com/pkg/errors"
 	corev1 "k8s.io/api/core/v1"
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
 	"k8s.io/klog/v2"
 	ctrl "sigs.k8s.io/controller-runtime"
@@ -342,7 +343,13 @@ func (r *DockerMachineReconciler) reconcileNormal(ctx context.Context, cluster *
 
 	// if the machine isn't bootstrapped, only then run bootstrap scripts
 	if !dockerMachine.Spec.Bootstrapped {
-		timeoutCtx, cancel := context.WithTimeout(ctx, 3*time.Minute)
+		var bootstrapTimeout metav1.Duration
+		if dockerMachine.Spec.BootstrapTimeout != nil {
+			bootstrapTimeout = *dockerMachine.Spec.BootstrapTimeout
+		} else {
+			bootstrapTimeout = metav1.Duration{Duration: 3 * time.Minute}
+		}
+		timeoutCtx, cancel := context.WithTimeout(ctx, bootstrapTimeout.Duration)
 		defer cancel()
 
 		// Check for bootstrap success