diff --git a/operator/charts/embedded-cluster-operator/charts/crds/templates/resources.yaml b/operator/charts/embedded-cluster-operator/charts/crds/templates/resources.yaml
index 605552f968..0230d99783 100644
--- a/operator/charts/embedded-cluster-operator/charts/crds/templates/resources.yaml
+++ b/operator/charts/embedded-cluster-operator/charts/crds/templates/resources.yaml
@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   labels:
     replicated.com/disaster-recovery: infra
     replicated.com/disaster-recovery-chart: embedded-cluster-operator
@@ -297,7 +297,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   labels:
     replicated.com/disaster-recovery: ec-install
   name: installations.embeddedcluster.replicated.com
diff --git a/operator/config/crd/bases/embeddedcluster.replicated.com_configs.yaml b/operator/config/crd/bases/embeddedcluster.replicated.com_configs.yaml
index 977eaf0b57..a79d342cff 100644
--- a/operator/config/crd/bases/embeddedcluster.replicated.com_configs.yaml
+++ b/operator/config/crd/bases/embeddedcluster.replicated.com_configs.yaml
@@ -3,7 +3,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   name: configs.embeddedcluster.replicated.com
 spec:
   group: embeddedcluster.replicated.com
diff --git a/operator/config/crd/bases/embeddedcluster.replicated.com_installations.yaml b/operator/config/crd/bases/embeddedcluster.replicated.com_installations.yaml
index 4f7bd9844d..e38cf3dac9 100644
--- a/operator/config/crd/bases/embeddedcluster.replicated.com_installations.yaml
+++ b/operator/config/crd/bases/embeddedcluster.replicated.com_installations.yaml
@@ -3,7 +3,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   name: installations.embeddedcluster.replicated.com
 spec:
   group: embeddedcluster.replicated.com
diff --git a/operator/config/crd/bases/embeddedcluster.replicated.com_kubernetesinstallations.yaml b/operator/config/crd/bases/embeddedcluster.replicated.com_kubernetesinstallations.yaml
index 600c44b98a..43a0f64f1e 100644
--- a/operator/config/crd/bases/embeddedcluster.replicated.com_kubernetesinstallations.yaml
+++ b/operator/config/crd/bases/embeddedcluster.replicated.com_kubernetesinstallations.yaml
@@ -3,7 +3,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   name: kubernetesinstallations.embeddedcluster.replicated.com
 spec:
   group: embeddedcluster.replicated.com
diff --git a/pkg/crds/resources.yaml b/pkg/crds/resources.yaml
index 605552f968..0230d99783 100644
--- a/pkg/crds/resources.yaml
+++ b/pkg/crds/resources.yaml
@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   labels:
     replicated.com/disaster-recovery: infra
     replicated.com/disaster-recovery-chart: embedded-cluster-operator
@@ -297,7 +297,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.19.0
+    controller-gen.kubebuilder.io/version: v0.20.0
   labels:
     replicated.com/disaster-recovery: ec-install
   name: installations.embeddedcluster.replicated.com
diff --git a/versions.mk b/versions.mk
index 7643f52ab5..e50c2d8de6 100644
--- a/versions.mk
+++ b/versions.mk
@@ -8,7 +8,7 @@ K0S_MINOR_VERSION ?= 33
 # K0S Versions
 K0S_VERSION_1_33 = v1.33.6+k0s.0
 K0S_VERSION_1_32 = v1.32.10+k0s.0
-K0S_VERSION_1_31 = v1.31.12+k0s.0
+K0S_VERSION_1_31 = v1.31.14+k0s.0
 K0S_VERSION_1_30 = v1.30.14+k0s.0
 K0S_VERSION_1_29 = v1.29.15+k0s.0
 
@@ -20,13 +20,13 @@ K0S_GO_VERSION = $(K0S_VERSION_1_$(K0S_MINOR_VERSION))
 TROUBLESHOOT_VERSION = v0.123.16
 
 # Helm Version
-HELM_VERSION = v3.19.2
+HELM_VERSION = v3.19.4
 
 # FIO Version (for performance testing)
 FIO_VERSION = 3.41
 
 # Kubernetes Development Tool Versions
-CONTROLLER_TOOLS_VERSION = v0.19.0
+CONTROLLER_TOOLS_VERSION = v0.20.0
 KUSTOMIZE_VERSION = v5.8.0
 
 ### Overrides ###