diff --git a/cluster/manifests/skipper/deployment.yaml b/cluster/manifests/skipper/deployment.yaml
index f31cb1d934..9905860dc8 100644
--- a/cluster/manifests/skipper/deployment.yaml
+++ b/cluster/manifests/skipper/deployment.yaml
@@ -1,7 +1,7 @@
 {{/* image-updater-bot detects *image variables so use print to disable it for main image */}}
 
 {{ $main_image := print "container-registry.zalando.net/teapot/skipper-internal:" "v0.21.224-1047" }}
-{{ $canary_image := "container-registry.zalando.net/teapot/skipper-internal:v0.21.224-1047" }}
+{{ $canary_image := "container-registry.zalando.net/teapot/skipper-internal:v0.21.240-1063" }}
 
 {{/* Optional canary arguments separated by "[cf724afc]" to allow whitespaces, e.g. "-foo=has a whitespace[cf724afc]-baz=qux" */}}
 {{ $canary_args := "" }}
diff --git a/cluster/manifests/skipper/hostname-credentials-controller.yaml b/cluster/manifests/skipper/hostname-credentials-controller.yaml
index 6b2bc11d54..6eb2e3fec5 100644
--- a/cluster/manifests/skipper/hostname-credentials-controller.yaml
+++ b/cluster/manifests/skipper/hostname-credentials-controller.yaml
@@ -1,5 +1,5 @@
 # {{ if eq .Cluster.ConfigItems.skipper_oauth2_ui_login "true" }}
-# {{ $image := "container-registry.zalando.net/gwproxy/hostname-credentials-controller:main-14" }}
+# {{ $image := "container-registry.zalando.net/gwproxy/hostname-credentials-controller:main-16" }}
 # {{ $version := index (split $image ":") 1 }}
 apiVersion: v1
 kind: ServiceAccount
diff --git a/cluster/node-pools/master-default/userdata.yaml b/cluster/node-pools/master-default/userdata.yaml
index 5a688895f9..41653d70af 100644
--- a/cluster/node-pools/master-default/userdata.yaml
+++ b/cluster/node-pools/master-default/userdata.yaml
@@ -247,7 +247,7 @@ write_files:
               name: admission-controller-kubeconfig
               readOnly: true
         - name: skipper-admission-webhook
-          image: 926694233939.dkr.ecr.eu-central-1.amazonaws.com/production_namespace/teapot/skipper:v0.21.230
+          image: 926694233939.dkr.ecr.eu-central-1.amazonaws.com/production_namespace/teapot/skipper:v0.21.240
           args:
             - webhook
             - --address=:9085
@@ -424,7 +424,7 @@ write_files:
             value: {{ .Cluster.ConfigItems.apiserver_business_partner_ids }}
 {{ end }}
         - name: skipper-proxy
-          image: 926694233939.dkr.ecr.eu-central-1.amazonaws.com/production_namespace/teapot/skipper:v0.21.230
+          image: 926694233939.dkr.ecr.eu-central-1.amazonaws.com/production_namespace/teapot/skipper:v0.21.240
           args:
           - skipper
           - -access-log-strip-query
@@ -475,7 +475,7 @@ write_files:
             name: ssl-certs-kubernetes
             readOnly: true
         - name: skipper-metrics
-          image: 926694233939.dkr.ecr.eu-central-1.amazonaws.com/production_namespace/teapot/skipper:v0.21.230
+          image: 926694233939.dkr.ecr.eu-central-1.amazonaws.com/production_namespace/teapot/skipper:v0.21.240
           args:
           - skipper
           - -access-log-strip-query