diff --git a/.gitignore b/.gitignore
index 26f97b110..1b4ea2f0a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -15,3 +15,4 @@ _artifacts/
 /vendor/
 bin/
 user.bazelrc
+*.bak
diff --git a/make/cluster.sh b/make/cluster.sh
index d705b2d06..3cbc3cf9b 100755
--- a/make/cluster.sh
+++ b/make/cluster.sh
@@ -23,7 +23,6 @@ set -e
 
 mode=kind
 k8s_version=1.23
-kind_image_repo=docker.io/kindest/node
 kind_cluster_name=kind
 
 help() {
@@ -45,6 +44,8 @@ Flags:
   --show-image
       Show the image that will be used for the cluster and exit with 0. The
       image will be of the form docker.io/kindest/node:1.23@sha256:498...81ac.
+  --update-images
+      Update the kind images to the latest version.
 
 Environment variables:
   ${green}K8S_VERSION${end}
@@ -53,7 +54,21 @@ EOF
   exit
 }
 
+# The below image digests can be refreshed with the command:
+#  make/cluster.sh --update-images
+images=$(
+  cat <<EOF
+docker.io/kindest/node:v1.18.0@sha256:0e20578828edd939d25eb98496a685c76c98d54084932f76069f886ec315d694
+docker.io/kindest/node:v1.19.0@sha256:3b0289b2d1bab2cb9108645a006939d2f447a10ad2bb21919c332d06b548bbc6
+docker.io/kindest/node:v1.20.0@sha256:b40ecf8bcb188f6a0d0f5d406089c48588b75edc112c6f635d26be5de1c89040
+docker.io/kindest/node:v1.21.1@sha256:f08bcc2d38416fa58b9857a1000dd69062b0c3024dcbd696373ea026abe38bbc
+docker.io/kindest/node:v1.22.0@sha256:b8bda84bb3a190e6e028b1760d277454a72267a5454b57db34437c34a588d047
+docker.io/kindest/node:v1.23.0@sha256:49824ab1727c04e56a21a5d8372a402fcd32ea51ac96a2706a12af38934f81ac
+EOF
+)
+
 show_image=
+update_images=
 while [ $# -ne 0 ]; do
   case "$1" in
   --*=*)
@@ -75,7 +90,7 @@ while [ $# -ne 0 ]; do
     eval "$var=$2"
     shift
     ;;
-  --show-image)
+  --show-image | --update-images)
     var=$1
     var=${var/--/}
     var=${var//-/_}
@@ -97,16 +112,25 @@ if printenv K8S_VERSION >/dev/null && [ -n "$K8S_VERSION" ]; then
   k8s_version="$K8S_VERSION"
 fi
 
-# NB: Kind cluster image digests are autogenerated by
-# hack/update-kind-images.sh.
-source "${here}/config/kind/kind_cluster_node_versions.env"
+if [ -n "$update_images" ]; then
+  for img in $images; do
+    sha=$(crane digest "$(cut -d@ -f1 <<<"$img")")
+    if [ "$(cut -d@ -f2 <<<"$img")" != "$sha" ]; then
+      trace sed -i.bak "s|^$img$|$(cut -d@ -f1 <<<"$img")@$sha|" "$0"
+    else
+      printf "${green}${greencheck}Info${end}: $img already uses the latest digest\n" >&2
+    fi
+  done
+  exit 0
+fi
+
 case "$k8s_version" in
-1.18*) image="${kind_image_repo}:v1.18.0@$KIND_IMAGE_SHA_K8S_118" ;;
-1.19*) image="${kind_image_repo}:v1.19.0@$KIND_IMAGE_SHA_K8S_119" ;;
-1.20*) image="${kind_image_repo}:v1.20.0@$KIND_IMAGE_SHA_K8S_120" ;;
-1.21*) image="${kind_image_repo}:v1.21.0@$KIND_IMAGE_SHA_K8S_121" ;;
-1.22*) image="${kind_image_repo}:v1.22.0@$KIND_IMAGE_SHA_K8S_122" ;;
-1.23*) image="${kind_image_repo}:v1.23.0@$KIND_IMAGE_SHA_K8S_123" ;;
+1.18*) image=$(grep -F 1.18 <<<"$images") ;;
+1.19*) image=$(grep -F 1.19 <<<"$images") ;;
+1.20*) image=$(grep -F 1.20 <<<"$images") ;;
+1.21*) image=$(grep -F 1.21 <<<"$images") ;;
+1.22*) image=$(grep -F 1.22 <<<"$images") ;;
+1.23*) image=$(grep -F 1.23 <<<"$images") ;;
 v*) printf "${red}${redcross}Error${end}: the Kubernetes version must be given without the leading 'v'\n" >&2 && exit 1 ;;
 *) printf "${red}${redcross}Error${end}: unsupported Kubernetes version ${yel}${k8s_version}${end}\n" >&2 && exit 1 ;;
 esac
diff --git a/make/config/kind/kind_cluster_node_versions.env b/make/config/kind/kind_cluster_node_versions.env
deleted file mode 100644
index 91a58053f..000000000
--- a/make/config/kind/kind_cluster_node_versions.env
+++ /dev/null
@@ -1,22 +0,0 @@
-# Copyright 2021 The cert-manager Authors.
-#
-# Licensed under the Apache License, Version 2.0 (the "License");
-# you may not use this file except in compliance with the License.
-# You may obtain a copy of the License at
-#
-#     http://www.apache.org/licenses/LICENSE-2.0
-#
-# Unless required by applicable law or agreed to in writing, software
-# distributed under the License is distributed on an "AS IS" BASIS,
-# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
-# See the License for the specific language governing permissions and
-# limitations under the License.
-
-# generated by ./hack/latest-kind-images.sh
-
-KIND_IMAGE_SHA_K8S_118=sha256:f4bcc97a0ad6e7abaf3f643d890add7efe6ee4ab90baeb374b4f41a4c95567eb
-KIND_IMAGE_SHA_K8S_119=sha256:a70639454e97a4b733f9d9b67e12c01f6b0297449d5b9cbbef87473458e26dca
-KIND_IMAGE_SHA_K8S_120=sha256:cbeaf907fc78ac97ce7b625e4bf0de16e3ea725daf6b04f930bd14c67c671ff9
-KIND_IMAGE_SHA_K8S_121=sha256:0fda882e43d425622f045b492f8bd83c2e0b4984fc03e2e05ec101ca1a685fb7
-KIND_IMAGE_SHA_K8S_122=sha256:f240c00ffb1d82a2a2225ca0f5c85d1c45aa2b97921327cb3f6da4eee7eae5c3
-KIND_IMAGE_SHA_K8S_123=sha256:49824ab1727c04e56a21a5d8372a402fcd32ea51ac96a2706a12af38934f81ac
\ No newline at end of file
diff --git a/make/tools.mk b/make/tools.mk
index 91e77c67f..7d406f6d5 100644
--- a/make/tools.mk
+++ b/make/tools.mk
@@ -409,3 +409,7 @@ ifneq ($(MISSING),)
 $(error Missing required tools: $(MISSING))
 endif
 endif
+
+.PHONY: e2e-setup-kind-update-images
+e2e-setup-kind-update-images: make/cluster.sh bin/tools/crane
+	make/cluster.sh --update-images