diff --git a/charts/spire/charts/spire-server/README.md b/charts/spire/charts/spire-server/README.md
index 108db58..6574da3 100644
--- a/charts/spire/charts/spire-server/README.md
+++ b/charts/spire/charts/spire-server/README.md
@@ -49,6 +49,10 @@ A Helm chart to install the SPIRE server.
 | controllerManager.service.port | int | `443` |  |
 | controllerManager.service.type | string | `"ClusterIP"` |  |
 | controllerManager.validatingWebhookConfiguration.failurePolicy | string | `"Fail"` |  |
+| controllerManager.validatingWebhookConfiguration.upgradeHook.image.pullPolicy | string | `"IfNotPresent"` |  |
+| controllerManager.validatingWebhookConfiguration.upgradeHook.image.registry | string | `"cgr.dev"` |  |
+| controllerManager.validatingWebhookConfiguration.upgradeHook.image.repository | string | `"chainguard/kubectl"` |  |
+| controllerManager.validatingWebhookConfiguration.upgradeHook.image.version | string | `"latest"` |  |
 | dataStorage.accessMode | string | `"ReadWriteOnce"` |  |
 | dataStorage.enabled | bool | `true` |  |
 | dataStorage.size | string | `"1Gi"` |  |
diff --git a/charts/spire/charts/spire-server/templates/controller-manager-webhook.yaml b/charts/spire/charts/spire-server/templates/controller-manager-webhook.yaml
index 1e55403..4216396 100644
--- a/charts/spire/charts/spire-server/templates/controller-manager-webhook.yaml
+++ b/charts/spire/charts/spire-server/templates/controller-manager-webhook.yaml
@@ -10,7 +10,7 @@ webhooks:
         name: {{ include "spire-controller-manager.fullname" . }}-webhook
         namespace: {{ include "spire-server.namespace" . }}
         path: /validate-spire-spiffe-io-v1alpha1-clusterfederatedtrustdomain
-    failurePolicy: {{ .Values.controllerManager.validatingWebhookConfiguration.failurePolicy }}
+    failurePolicy: Ignore # Actual value to be set by post install/upgrade hooks
     name: vclusterfederatedtrustdomain.kb.io
     rules:
       - apiGroups: ["spire.spiffe.io"]
@@ -24,7 +24,7 @@ webhooks:
         name: {{ include "spire-controller-manager.fullname" . }}-webhook
         namespace: {{ include "spire-server.namespace" . }}
         path: /validate-spire-spiffe-io-v1alpha1-clusterspiffeid
-    failurePolicy: {{ .Values.controllerManager.validatingWebhookConfiguration.failurePolicy }}
+    failurePolicy: Ignore # Actual value to be set by post install/upgrade hooks
     name: vclusterspiffeid.kb.io
     rules:
       - apiGroups: ["spire.spiffe.io"]
diff --git a/charts/spire/charts/spire-server/templates/post-install-hook.yaml b/charts/spire/charts/spire-server/templates/post-install-hook.yaml
new file mode 100644
index 0000000..d30893d
--- /dev/null
+++ b/charts/spire/charts/spire-server/templates/post-install-hook.yaml
@@ -0,0 +1,85 @@
+{{- if eq (.Values.controllerManager.enabled | toString) "true" }}
+{{- if eq .Values.controllerManager.validatingWebhookConfiguration.failurePolicy "Fail" }}
+apiVersion: v1
+kind: ServiceAccount
+metadata:
+  name: {{ include "spire-server.serviceAccountName" . }}-post-install
+  namespace: {{ include "spire-server.namespace" . }}
+  labels:
+    {{- include "spire-server.labels" . | nindent 4 }}
+  annotations:
+    "helm.sh/hook": post-install
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRole
+metadata:
+  name: {{ include "spire-server.fullname" . }}-post-install
+  annotations:
+    "helm.sh/hook": post-install
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+rules:
+  - apiGroups: ["admissionregistration.k8s.io"]
+    resources: ["validatingwebhookconfigurations"]
+    resourceNames: [{{ printf "%s-webhook"  (include "spire-controller-manager.fullname" .) | quote }}]
+    verbs: ["get", "patch"]
+---
+kind: ClusterRoleBinding
+apiVersion: rbac.authorization.k8s.io/v1
+metadata:
+  name: {{ include "spire-server.fullname" . }}-post-install
+  annotations:
+    "helm.sh/hook": post-install
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+subjects:
+  - kind: ServiceAccount
+    name: {{ include "spire-server.serviceAccountName" . }}-post-install
+    namespace: {{ include "spire-server.namespace" . }}
+roleRef:
+  kind: ClusterRole
+  name: {{ include "spire-server.fullname" . }}-post-install
+  apiGroup: rbac.authorization.k8s.io
+---
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: {{ include "spire-server.fullname" . }}-post-install
+  namespace: {{ include "spire-server.namespace" . }}
+  labels:
+    {{- include "spire-server.labels" . | nindent 4 }}
+  annotations:
+    "helm.sh/hook": post-install
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+spec:
+  template:
+    metadata:
+      name: {{ include "spire-server.fullname" . }}-post-install
+    spec:
+      restartPolicy: Never
+      serviceAccountName: {{ include "spire-server.serviceAccountName" . }}-post-install
+      securityContext:
+        {{- toYaml .Values.podSecurityContext | nindent 8 }}
+      containers:
+      - name: post-install-job
+        securityContext:
+          {{- toYaml .Values.securityContext | nindent 10 }}
+        image: {{ template "spire-server.image" (dict "appVersion" $.Chart.AppVersion "image" .Values.controllerManager.validatingWebhookConfiguration.upgradeHook.image) }}
+        command:
+        - /bin/sh
+        - -c
+        - |-
+          kubectl patch validatingwebhookconfiguration {{ include "spire-controller-manager.fullname" . }}-webhook --type='strategic' -p '
+          {
+            "webhooks":[
+              {
+                "name":"vclusterspiffeid.kb.io",
+                "failurePolicy":"{{ .Values.controllerManager.validatingWebhookConfiguration.failurePolicy }}"
+              },
+              {
+                "name":"vclusterfederatedtrustdomain.kb.io",
+                "failurePolicy":"{{ .Values.controllerManager.validatingWebhookConfiguration.failurePolicy }}"
+              }
+            ]
+          }'
+{{- end }}
+{{- end }}
diff --git a/charts/spire/charts/spire-server/templates/post-upgrade-hook.yaml b/charts/spire/charts/spire-server/templates/post-upgrade-hook.yaml
new file mode 100644
index 0000000..a6fd319
--- /dev/null
+++ b/charts/spire/charts/spire-server/templates/post-upgrade-hook.yaml
@@ -0,0 +1,85 @@
+{{- if eq (.Values.controllerManager.enabled | toString) "true" }}
+{{- if eq .Values.controllerManager.validatingWebhookConfiguration.failurePolicy "Fail" }}
+apiVersion: v1
+kind: ServiceAccount
+metadata:
+  name: {{ include "spire-server.serviceAccountName" . }}-post-upgrade
+  namespace: {{ include "spire-server.namespace" . }}
+  labels:
+    {{- include "spire-server.labels" . | nindent 4 }}
+  annotations:
+    "helm.sh/hook": post-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRole
+metadata:
+  name: {{ include "spire-server.fullname" . }}-post-upgrade
+  annotations:
+    "helm.sh/hook": post-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+rules:
+  - apiGroups: ["admissionregistration.k8s.io"]
+    resources: ["validatingwebhookconfigurations"]
+    resourceNames: [{{ printf "%s-webhook"  (include "spire-controller-manager.fullname" .) | quote }}]
+    verbs: ["get", "patch"]
+---
+kind: ClusterRoleBinding
+apiVersion: rbac.authorization.k8s.io/v1
+metadata:
+  name: {{ include "spire-server.fullname" . }}-post-upgrade
+  annotations:
+    "helm.sh/hook": post-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+subjects:
+  - kind: ServiceAccount
+    name: {{ include "spire-server.serviceAccountName" . }}-post-upgrade
+    namespace: {{ include "spire-server.namespace" . }}
+roleRef:
+  kind: ClusterRole
+  name: {{ include "spire-server.fullname" . }}-post-upgrade
+  apiGroup: rbac.authorization.k8s.io
+---
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: {{ include "spire-server.fullname" . }}-post-upgrade
+  namespace: {{ include "spire-server.namespace" . }}
+  labels:
+    {{- include "spire-server.labels" . | nindent 4 }}
+  annotations:
+    "helm.sh/hook": post-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+spec:
+  template:
+    metadata:
+      name: {{ include "spire-server.fullname" . }}-post-upgrade
+    spec:
+      restartPolicy: Never
+      serviceAccountName: {{ include "spire-server.serviceAccountName" . }}-post-upgrade 
+      securityContext:
+        {{- toYaml .Values.podSecurityContext | nindent 8 }}
+      containers:
+      - name: post-upgrade-job
+        securityContext:
+          {{- toYaml .Values.securityContext | nindent 10 }}
+        image: {{ template "spire-server.image" (dict "appVersion" $.Chart.AppVersion "image" .Values.controllerManager.validatingWebhookConfiguration.upgradeHook.image) }}
+        command:
+        - /bin/sh
+        - -c
+        - |-
+          kubectl patch validatingwebhookconfiguration {{ include "spire-controller-manager.fullname" . }}-webhook --type='strategic' -p '
+          {
+            "webhooks":[
+              {
+                "name":"vclusterspiffeid.kb.io",
+                "failurePolicy":"{{ .Values.controllerManager.validatingWebhookConfiguration.failurePolicy }}"
+              },
+              {
+                "name":"vclusterfederatedtrustdomain.kb.io",
+                "failurePolicy":"{{ .Values.controllerManager.validatingWebhookConfiguration.failurePolicy }}"
+              }
+            ]
+          }'
+{{- end }}
+{{- end }}
diff --git a/charts/spire/charts/spire-server/templates/pre-upgrade-hook.yaml b/charts/spire/charts/spire-server/templates/pre-upgrade-hook.yaml
new file mode 100644
index 0000000..bf4fa74
--- /dev/null
+++ b/charts/spire/charts/spire-server/templates/pre-upgrade-hook.yaml
@@ -0,0 +1,85 @@
+{{- if eq (.Values.controllerManager.enabled | toString) "true" }}
+{{- if eq .Values.controllerManager.validatingWebhookConfiguration.failurePolicy "Fail" }}
+apiVersion: v1
+kind: ServiceAccount
+metadata:
+  name: {{ include "spire-server.serviceAccountName" . }}-pre-upgrade
+  namespace: {{ include "spire-server.namespace" . }}
+  labels:
+    {{- include "spire-server.labels" . | nindent 4 }}
+  annotations:
+    "helm.sh/hook": pre-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRole
+metadata:
+  name: {{ include "spire-server.fullname" . }}-pre-upgrade
+  annotations:
+    "helm.sh/hook": pre-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+rules:
+  - apiGroups: ["admissionregistration.k8s.io"]
+    resources: ["validatingwebhookconfigurations"]
+    resourceNames: [{{ printf "%s-webhook"  (include "spire-controller-manager.fullname" .) | quote }}]
+    verbs: ["get", "patch"]
+---
+kind: ClusterRoleBinding
+apiVersion: rbac.authorization.k8s.io/v1
+metadata:
+  name: {{ include "spire-server.fullname" . }}-pre-upgrade
+  annotations:
+    "helm.sh/hook": pre-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+subjects:
+  - kind: ServiceAccount
+    name: {{ include "spire-server.serviceAccountName" . }}-pre-upgrade
+    namespace: {{ include "spire-server.namespace" . }}
+roleRef:
+  kind: ClusterRole
+  name: {{ include "spire-server.fullname" . }}-pre-upgrade
+  apiGroup: rbac.authorization.k8s.io
+---
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: {{ include "spire-server.fullname" . }}-pre-upgrade
+  namespace: {{ include "spire-server.namespace" . }}
+  labels:
+    {{- include "spire-server.labels" . | nindent 4 }}
+  annotations:
+    "helm.sh/hook": pre-upgrade
+    "helm.sh/hook-delete-policy": hook-succeeded, hook-failed
+spec:
+  template:
+    metadata:
+      name: {{ include "spire-server.fullname" . }}-pre-upgrade
+    spec:
+      restartPolicy: Never
+      serviceAccountName: {{ include "spire-server.serviceAccountName" . }}-pre-upgrade
+      securityContext:
+        {{- toYaml .Values.podSecurityContext | nindent 8 }}
+      containers:
+      - name: post-install-job
+        securityContext:
+          {{- toYaml .Values.securityContext | nindent 10 }}
+        image: {{ template "spire-server.image" (dict "appVersion" $.Chart.AppVersion "image" .Values.controllerManager.validatingWebhookConfiguration.upgradeHook.image) }}
+        command:
+        - /bin/sh
+        - -c
+        - |-
+          kubectl patch validatingwebhookconfiguration {{ include "spire-controller-manager.fullname" . }}-webhook --type='strategic' -p '
+          {
+            "webhooks":[
+              {
+                "name":"vclusterspiffeid.kb.io",
+                "failurePolicy":"Ignore"
+              },
+              {
+                "name":"vclusterfederatedtrustdomain.kb.io",
+                "failurePolicy":"Ignore"
+              }
+            ]
+          }'
+{{- end }}
+{{- end }}
diff --git a/charts/spire/charts/spire-server/values.yaml b/charts/spire/charts/spire-server/values.yaml
index 61df91c..76274fd 100644
--- a/charts/spire/charts/spire-server/values.yaml
+++ b/charts/spire/charts/spire-server/values.yaml
@@ -185,6 +185,12 @@ controllerManager:
 
   validatingWebhookConfiguration:
     failurePolicy: Fail
+    upgradeHook:
+      image:
+        registry: cgr.dev
+        repository: chainguard/kubectl
+        pullPolicy: IfNotPresent
+        version: latest
 
 telemetry:
   prometheus: