diff --git a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-main-upgrades.yaml b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-main-upgrades.yaml
index 7fded6e52bd1e..19f2c005fd714 100644
--- a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-main-upgrades.yaml
+++ b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-main-upgrades.yaml
@@ -255,7 +255,7 @@ periodics:
     testgrid-alert-email: sig-cluster-lifecycle-cluster-api-alerts@kubernetes.io
     testgrid-num-failures-to-alert: "4"
 
-- name: periodic-cluster-api-e2e-workload-upgrade-1-26-latest-main
+- name: periodic-cluster-api-e2e-workload-upgrade-1-26-1-27-main
   interval: 24h
   decorate: true
   decoration_config:
@@ -287,7 +287,7 @@ periodics:
       - name: KUBERNETES_VERSION_UPGRADE_FROM
         value: "stable-1.26"
       - name: KUBERNETES_VERSION_UPGRADE_TO
-        value: "ci/latest-1.27"
+        value: "stable-1.27"
       - name: ETCD_VERSION_UPGRADE_TO
         value: "3.5.6-0"
       - name: COREDNS_VERSION_UPGRADE_TO
@@ -302,6 +302,57 @@ periodics:
           cpu: 7300m
   annotations:
     testgrid-dashboards: sig-cluster-lifecycle-cluster-api
-    testgrid-tab-name: capi-e2e-main-1-26-latest
+    testgrid-tab-name: capi-e2e-main-1-26-1-27
+    testgrid-alert-email: sig-cluster-lifecycle-cluster-api-alerts@kubernetes.io
+    testgrid-num-failures-to-alert: "4"
+
+- name: periodic-cluster-api-e2e-workload-upgrade-1-27-latest-main
+  interval: 24h
+  decorate: true
+  decoration_config:
+    gcs_credentials_secret: "" # Use workload identity for uploading artifacts
+  rerun_auth_config:
+    github_team_slugs:
+    - org: kubernetes-sigs
+      slug: cluster-api-maintainers
+  labels:
+    preset-dind-enabled: "true"
+    preset-kind-volume-mounts: "true"
+  extra_refs:
+  - org: kubernetes-sigs
+    repo: cluster-api
+    base_ref: main
+    path_alias: sigs.k8s.io/cluster-api
+  - org: kubernetes
+    repo: kubernetes
+    base_ref: master
+    path_alias: k8s.io/kubernetes
+  spec:
+    serviceAccountName: prowjob-default-sa
+    containers:
+    - image: gcr.io/k8s-staging-test-infra/kubekins-e2e:v20230406-23cb1879e3-1.26
+      args:
+      - runner.sh
+      - "./scripts/ci-e2e.sh"
+      env:
+      - name: KUBERNETES_VERSION_UPGRADE_FROM
+        value: "stable-1.27"
+      - name: KUBERNETES_VERSION_UPGRADE_TO
+        value: "ci/latest-1.28"
+      - name: ETCD_VERSION_UPGRADE_TO
+        value: "3.5.7-0"
+      - name: COREDNS_VERSION_UPGRADE_TO
+        value: "v1.9.3"
+      - name: GINKGO_FOCUS
+        value: "\\[K8s-Upgrade\\]"
+      # we need privileged mode in order to do docker in docker
+      securityContext:
+        privileged: true
+      resources:
+        requests:
+          cpu: 7300m
+  annotations:
+    testgrid-dashboards: sig-cluster-lifecycle-cluster-api
+    testgrid-tab-name: capi-e2e-main-1-27-latest
     testgrid-alert-email: sig-cluster-lifecycle-cluster-api-alerts@kubernetes.io
     testgrid-num-failures-to-alert: "4"
diff --git a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-release-1-4-upgrades.yaml b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-release-1-4-upgrades.yaml
index 1e5155fd297e7..7e6f372cd3ce5 100644
--- a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-release-1-4-upgrades.yaml
+++ b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-periodics-release-1-4-upgrades.yaml
@@ -254,7 +254,7 @@ periodics:
     testgrid-alert-email: sig-cluster-lifecycle-cluster-api-alerts@kubernetes.io
     testgrid-num-failures-to-alert: "4"
 
-- name: periodic-cluster-api-e2e-workload-upgrade-1-26-latest-release-1-4
+- name: periodic-cluster-api-e2e-workload-upgrade-1-26-1-27-release-1-4
   interval: 24h
   decorate: true
   decoration_config:
@@ -286,7 +286,7 @@ periodics:
           - name: KUBERNETES_VERSION_UPGRADE_FROM
             value: "stable-1.26"
           - name: KUBERNETES_VERSION_UPGRADE_TO
-            value: "ci/latest-1.27"
+            value: "stable-1.27"
           - name: ETCD_VERSION_UPGRADE_TO
             value: "3.5.6-0"
           - name: COREDNS_VERSION_UPGRADE_TO
@@ -301,6 +301,57 @@ periodics:
             cpu: 7300m
   annotations:
     testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.4
-    testgrid-tab-name: capi-e2e-release-1-4-1-26-latest
+    testgrid-tab-name: capi-e2e-release-1-4-1-26-1-27
+    testgrid-alert-email: sig-cluster-lifecycle-cluster-api-alerts@kubernetes.io
+    testgrid-num-failures-to-alert: "4"
+
+- name: periodic-cluster-api-e2e-workload-upgrade-1-27-latest-release-1-4
+  interval: 24h
+  decorate: true
+  decoration_config:
+    gcs_credentials_secret: "" # Use workload identity for uploading artifacts
+  rerun_auth_config:
+    github_team_slugs:
+      - org: kubernetes-sigs
+        slug: cluster-api-maintainers
+  labels:
+    preset-dind-enabled: "true"
+    preset-kind-volume-mounts: "true"
+  extra_refs:
+    - org: kubernetes-sigs
+      repo: cluster-api
+      base_ref: release-1.4
+      path_alias: sigs.k8s.io/cluster-api
+    - org: kubernetes
+      repo: kubernetes
+      base_ref: master
+      path_alias: k8s.io/kubernetes
+  spec:
+    serviceAccountName: prowjob-default-sa
+    containers:
+      - image: gcr.io/k8s-staging-test-infra/kubekins-e2e:v20230406-23cb1879e3-1.26
+        args:
+          - runner.sh
+          - "./scripts/ci-e2e.sh"
+        env:
+          - name: KUBERNETES_VERSION_UPGRADE_FROM
+            value: "stable-1.27"
+          - name: KUBERNETES_VERSION_UPGRADE_TO
+            value: "ci/latest-1.28"
+          - name: ETCD_VERSION_UPGRADE_TO
+            value: "3.5.7-0"
+          - name: COREDNS_VERSION_UPGRADE_TO
+            value: "v1.9.3"
+          - name: GINKGO_FOCUS
+            value: "\\[K8s-Upgrade\\]"
+        # we need privileged mode in order to do docker in docker
+        securityContext:
+          privileged: true
+        resources:
+          requests:
+            cpu: 7300m
+  annotations:
+    testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.4
+    testgrid-tab-name: capi-e2e-release-1-4-1-27-latest
     testgrid-alert-email: sig-cluster-lifecycle-cluster-api-alerts@kubernetes.io
     testgrid-num-failures-to-alert: "4"
diff --git a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-2.yaml b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-2.yaml
index fac584e5d6449..f971d6413ff52 100644
--- a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-2.yaml
+++ b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-2.yaml
@@ -250,7 +250,7 @@ presubmits:
     annotations:
       testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.2
       testgrid-tab-name: capi-pr-e2e-full-release-1-2
-  - name: pull-cluster-api-e2e-workload-upgrade-1-26-latest-release-1-2
+  - name: pull-cluster-api-e2e-workload-upgrade-1-27-latest-release-1-2
     labels:
       preset-dind-enabled: "true"
       preset-kind-volume-mounts: "true"
@@ -277,11 +277,11 @@ presubmits:
           - "./scripts/ci-e2e.sh"
         env:
           - name: KUBERNETES_VERSION_UPGRADE_FROM
-            value: "stable-1.26"
+            value: "stable-1.27"
           - name: KUBERNETES_VERSION_UPGRADE_TO
-            value: "ci/latest-1.27"
+            value: "ci/latest-1.28"
           - name: ETCD_VERSION_UPGRADE_TO
-            value: "3.5.6-0"
+            value: "3.5.7-0"
           - name: COREDNS_VERSION_UPGRADE_TO
             value: "v1.9.3"
           - name: GINKGO_FOCUS
@@ -294,4 +294,4 @@ presubmits:
             cpu: 7300m
     annotations:
       testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.2
-      testgrid-tab-name: capi-pr-e2e-release-1-2-1-26-latest
+      testgrid-tab-name: capi-pr-e2e-release-1-2-1-27-latest
diff --git a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-3.yaml b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-3.yaml
index b126ded2889c9..6d0a140f0ba19 100644
--- a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-3.yaml
+++ b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-3.yaml
@@ -245,7 +245,7 @@ presubmits:
     annotations:
       testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.3
       testgrid-tab-name: capi-pr-e2e-full-release-1-3
-  - name: pull-cluster-api-e2e-workload-upgrade-1-26-latest-release-1-3
+  - name: pull-cluster-api-e2e-workload-upgrade-1-27-latest-release-1-3
     labels:
       preset-dind-enabled: "true"
       preset-kind-volume-mounts: "true"
@@ -271,11 +271,11 @@ presubmits:
           - "./scripts/ci-e2e.sh"
         env:
           - name: KUBERNETES_VERSION_UPGRADE_FROM
-            value: "stable-1.26"
+            value: "stable-1.27"
           - name: KUBERNETES_VERSION_UPGRADE_TO
-            value: "ci/latest-1.27"
+            value: "ci/latest-1.28"
           - name: ETCD_VERSION_UPGRADE_TO
-            value: "3.5.6-0"
+            value: "3.5.7-0"
           - name: COREDNS_VERSION_UPGRADE_TO
             value: "v1.9.3"
           - name: GINKGO_FOCUS
@@ -288,4 +288,4 @@ presubmits:
             cpu: 7300m
     annotations:
       testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.3
-      testgrid-tab-name: capi-pr-e2e-release-1-3-1-26-latest
+      testgrid-tab-name: capi-pr-e2e-release-1-3-1-27-latest
diff --git a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-4.yaml b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-4.yaml
index 98e998ebbe1e3..19d3e8e6b1527 100644
--- a/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-4.yaml
+++ b/config/jobs/kubernetes-sigs/cluster-api/cluster-api-presubmits-release-1-4.yaml
@@ -254,7 +254,7 @@ presubmits:
     annotations:
       testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.4
       testgrid-tab-name: capi-pr-e2e-full-release-1-4
-  - name: pull-cluster-api-e2e-workload-upgrade-1-26-latest-release-1-4
+  - name: pull-cluster-api-e2e-workload-upgrade-1-27-latest-release-1-4
     labels:
       preset-dind-enabled: "true"
       preset-kind-volume-mounts: "true"
@@ -281,11 +281,11 @@ presubmits:
             - "./scripts/ci-e2e.sh"
           env:
             - name: KUBERNETES_VERSION_UPGRADE_FROM
-              value: "stable-1.26"
+              value: "stable-1.27"
             - name: KUBERNETES_VERSION_UPGRADE_TO
-              value: "ci/latest-1.27"
+              value: "ci/latest-1.28"
             - name: ETCD_VERSION_UPGRADE_TO
-              value: "3.5.6-0"
+              value: "3.5.7-0"
             - name: COREDNS_VERSION_UPGRADE_TO
               value: "v1.9.3"
             - name: GINKGO_FOCUS
@@ -298,7 +298,7 @@ presubmits:
               cpu: 7300m
     annotations:
       testgrid-dashboards: sig-cluster-lifecycle-cluster-api-1.4
-      testgrid-tab-name: capi-pr-e2e-release-1-4-1-26-latest
+      testgrid-tab-name: capi-pr-e2e-release-1-4-1-27-latest
   # This job is experimental for now. Please do not duplicate it to release branches.
   - name: pull-cluster-api-e2e-scale-release-1-4-experimental
     labels: