diff --git a/controller/linodemachine_controller_helpers.go b/controller/linodemachine_controller_helpers.go
index cbc7299c..44a17431 100644
--- a/controller/linodemachine_controller_helpers.go
+++ b/controller/linodemachine_controller_helpers.go
@@ -50,11 +50,10 @@ import (
 	"github.com/linode/cluster-api-provider-linode/util/reconciler"
 )
 
-// Size limit in bytes on the decoded metadata.user_data for cloud-init
-// The decoded user_data must not exceed 16384 bytes per the Linode API
 const (
-	maxBootstrapDataBytes = 16384
-	vlanIPFormat          = "%s/11"
+	maxBootstrapDataBytesCloudInit   = 16384
+	maxBootstrapDataBytesStackscript = 65535
+	vlanIPFormat                     = "%s/11"
 )
 
 var (
@@ -473,21 +472,29 @@ func setUserData(ctx context.Context, machineScope *scope.MachineScope, createCo
 
 		return err
 	}
-	if len(bootstrapData) > maxBootstrapDataBytes {
-		err = errors.New("bootstrap data too large")
-		logger.Error(err, "decoded bootstrap data exceeds size limit",
-			"limit", maxBootstrapDataBytes,
-		)
-
-		return err
-	}
 
 	if machineScope.LinodeMachine.Status.CloudinitMetadataSupport {
+		if len(bootstrapData) > maxBootstrapDataBytesCloudInit {
+			err = errors.New("bootstrap data too large")
+			logger.Error(err, "decoded bootstrap data exceeds size limit",
+				"limit", maxBootstrapDataBytesCloudInit,
+			)
+
+			return err
+		}
 		createConfig.Metadata = &linodego.InstanceMetadataOptions{
 			UserData: b64.StdEncoding.EncodeToString(bootstrapData),
 		}
 	} else {
 		logger.Info("using StackScripts for bootstrapping")
+		if len(bootstrapData) > maxBootstrapDataBytesStackscript {
+			err = errors.New("bootstrap data too large")
+			logger.Error(err, "decoded bootstrap data exceeds size limit",
+				"limit", maxBootstrapDataBytesStackscript,
+			)
+
+			return err
+		}
 		capiStackScriptID, err := services.EnsureStackscript(ctx, machineScope)
 		if err != nil {
 			return fmt.Errorf("ensure stackscript: %w", err)
diff --git a/controller/linodemachine_controller_helpers_test.go b/controller/linodemachine_controller_helpers_test.go
index 88c38a55..789a4d96 100644
--- a/controller/linodemachine_controller_helpers_test.go
+++ b/controller/linodemachine_controller_helpers_test.go
@@ -161,7 +161,7 @@ func TestSetUserData(t *testing.T) {
 			},
 		},
 		{
-			name: "Error - SetUserData large bootstrap data",
+			name: "Error - SetUserData large bootstrap data for cloud-init",
 			machineScope: &scope.MachineScope{Machine: &v1beta1.Machine{
 				Spec: v1beta1.MachineSpec{
 					ClusterName: "",
@@ -176,7 +176,40 @@ func TestSetUserData(t *testing.T) {
 					Namespace: "default",
 				},
 				Spec:   infrav1alpha2.LinodeMachineSpec{Region: "us-ord", Image: "linode/ubuntu22.04"},
-				Status: infrav1alpha2.LinodeMachineStatus{},
+				Status: infrav1alpha2.LinodeMachineStatus{CloudinitMetadataSupport: true},
+			}},
+			createConfig: &linodego.InstanceCreateOptions{},
+			wantConfig:   &linodego.InstanceCreateOptions{},
+			expects: func(mockClient *mock.MockLinodeClient, kMock *mock.MockK8sClient) {
+				kMock.EXPECT().Get(gomock.Any(), gomock.Any(), gomock.Any()).DoAndReturn(func(ctx context.Context, key types.NamespacedName, obj *corev1.Secret, opts ...client.GetOption) error {
+					cred := corev1.Secret{
+						Data: map[string][]byte{
+							"value": make([]byte, maxBootstrapDataBytesCloudInit+1),
+						},
+					}
+					*obj = cred
+					return nil
+				})
+			},
+			expectedError: fmt.Errorf("bootstrap data too large"),
+		},
+		{
+			name: "Error - SetUserData large bootstrap data for stackscript",
+			machineScope: &scope.MachineScope{Machine: &v1beta1.Machine{
+				Spec: v1beta1.MachineSpec{
+					ClusterName: "",
+					Bootstrap: v1beta1.Bootstrap{
+						DataSecretName: ptr.To("test-data"),
+					},
+					InfrastructureRef: corev1.ObjectReference{},
+				},
+			}, LinodeMachine: &infrav1alpha2.LinodeMachine{
+				ObjectMeta: metav1.ObjectMeta{
+					Name:      "test-cluster",
+					Namespace: "default",
+				},
+				Spec:   infrav1alpha2.LinodeMachineSpec{Region: "us-ord", Image: "linode/ubuntu22.04"},
+				Status: infrav1alpha2.LinodeMachineStatus{CloudinitMetadataSupport: false},
 			}},
 			createConfig: &linodego.InstanceCreateOptions{},
 			wantConfig:   &linodego.InstanceCreateOptions{},
@@ -184,7 +217,7 @@ func TestSetUserData(t *testing.T) {
 				kMock.EXPECT().Get(gomock.Any(), gomock.Any(), gomock.Any()).DoAndReturn(func(ctx context.Context, key types.NamespacedName, obj *corev1.Secret, opts ...client.GetOption) error {
 					cred := corev1.Secret{
 						Data: map[string][]byte{
-							"value": make([]byte, maxBootstrapDataBytes+1),
+							"value": make([]byte, maxBootstrapDataBytesStackscript+1),
 						},
 					}
 					*obj = cred