diff --git a/Makefile b/Makefile
index ad0b4ecc28f..b2c8eecdbf6 100644
--- a/Makefile
+++ b/Makefile
@@ -300,7 +300,7 @@ create-management-cluster: $(KUSTOMIZE) $(ENVSUBST) $(KUBECTL) $(KIND) ## Create
 	./hack/create-custom-cloud-provider-config.sh
 
 	# Deploy CAPI
-	timeout --foreground 300 bash -c "until curl --retry $(CURL_RETRIES) -sSL https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.5/cluster-api-components.yaml | $(ENVSUBST) | $(KUBECTL) apply -f -; do sleep 5; done"
+	timeout --foreground 300 bash -c "until curl --retry $(CURL_RETRIES) -sSL https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.6/cluster-api-components.yaml | $(ENVSUBST) | $(KUBECTL) apply -f -; do sleep 5; done"
 
 	# Deploy CAAPH
 	timeout --foreground 300 bash -c "until curl --retry $(CURL_RETRIES) -sSL https://github.com/kubernetes-sigs/cluster-api-addon-provider-helm/releases/download/v0.1.0-alpha.10/addon-components.yaml | $(ENVSUBST) | $(KUBECTL) apply -f -; do sleep 5; done"
diff --git a/Tiltfile b/Tiltfile
index eefbd3b1ab3..61444fbb02e 100644
--- a/Tiltfile
+++ b/Tiltfile
@@ -20,9 +20,9 @@ settings = {
     "deploy_cert_manager": True,
     "preload_images_for_kind": True,
     "kind_cluster_name": "capz",
-    "capi_version": "v1.6.5",
-    "cert_manager_version": "v1.14.5",
-    "capi_version": "v1.6.5",
+    "capi_version": "v1.6.6",
+    "cert_manager_version": "v1.15.0",
+    "capi_version": "v1.6.6",
     "kubernetes_version": "v1.28.3",
     "aks_kubernetes_version": "v1.28.3",
     "flatcar_version": "3374.2.1",
diff --git a/go.mod b/go.mod
index 7cbd39ba45f..657162eb097 100644
--- a/go.mod
+++ b/go.mod
@@ -54,8 +54,8 @@ require (
 	k8s.io/kubectl v0.28.4
 	k8s.io/utils v0.0.0-20230726121419-3b25d923346b
 	sigs.k8s.io/cloud-provider-azure v1.28.4
-	sigs.k8s.io/cluster-api v1.6.5
-	sigs.k8s.io/cluster-api/test v1.6.5
+	sigs.k8s.io/cluster-api v1.6.6
+	sigs.k8s.io/cluster-api/test v1.6.6
 	sigs.k8s.io/controller-runtime v0.16.5
 	sigs.k8s.io/kind v0.22.0
 )
@@ -219,7 +219,7 @@ require (
 	sigs.k8s.io/yaml v1.4.0 // indirect
 )
 
-replace sigs.k8s.io/cluster-api => sigs.k8s.io/cluster-api v1.6.5
+replace sigs.k8s.io/cluster-api => sigs.k8s.io/cluster-api v1.6.6
 
 // kube-openapi should match the version imported by CAPI.
 replace k8s.io/kube-openapi => k8s.io/kube-openapi v0.0.0-20230717233707-2695361300d9
diff --git a/go.sum b/go.sum
index c3911883ce7..f2f17e5d694 100644
--- a/go.sum
+++ b/go.sum
@@ -999,10 +999,10 @@ sigs.k8s.io/apiserver-network-proxy/konnectivity-client v0.1.2 h1:trsWhjU5jZrx6U
 sigs.k8s.io/apiserver-network-proxy/konnectivity-client v0.1.2/go.mod h1:+qG7ISXqCDVVcyO8hLn12AKVYYUjM7ftlqsqmrhMZE0=
 sigs.k8s.io/cloud-provider-azure v1.28.4 h1:TG/N0fjnZT+T53ymdoHvl3ft6QXvHcx8U7b6lcC1tC0=
 sigs.k8s.io/cloud-provider-azure v1.28.4/go.mod h1:xtm6ROi1sIRLF8otWohSfrwAkVHCOk+dJ9xvB4QAXUU=
-sigs.k8s.io/cluster-api v1.6.5 h1:9M5uDy+kih9xltpayWbVGEiATMJIdOqe1ejzt6IQ6IA=
-sigs.k8s.io/cluster-api v1.6.5/go.mod h1:az1S/g/6umDjmh3ZWpjJWm23peUZOqEt3vv2FuOIZ3s=
-sigs.k8s.io/cluster-api/test v1.6.5 h1:kId67PyHbg/ffqTfFI0aVxaJ1DBON+l32d1GpmMNW/o=
-sigs.k8s.io/cluster-api/test v1.6.5/go.mod h1:QimdqQoykUpYpUKkpIabhj8R34wAzw7akMwlCc65xeA=
+sigs.k8s.io/cluster-api v1.6.6 h1:xXUHwM+4ZENzesQQSpRRtCRlBuW9fgknbgjwr0tHSfE=
+sigs.k8s.io/cluster-api v1.6.6/go.mod h1:az1S/g/6umDjmh3ZWpjJWm23peUZOqEt3vv2FuOIZ3s=
+sigs.k8s.io/cluster-api/test v1.6.6 h1:Xb+mVv+Wq+R1RR7wPZOcQpcAWcTGeOPaavYG0tBmUDQ=
+sigs.k8s.io/cluster-api/test v1.6.6/go.mod h1:QimdqQoykUpYpUKkpIabhj8R34wAzw7akMwlCc65xeA=
 sigs.k8s.io/controller-runtime v0.16.5 h1:yr1cEJbX08xsTW6XEIzT13KHHmIyX8Umvme2cULvFZw=
 sigs.k8s.io/controller-runtime v0.16.5/go.mod h1:j7bialYoSn142nv9sCOJmQgDXQXxnroFU4VnX/brVJ0=
 sigs.k8s.io/json v0.0.0-20221116044647-bc3834ca7abd h1:EDPBXCAspyGV4jQlpZSudPeMmr1bNJefnuqLsRAsHZo=
diff --git a/hack/install-cert-manager.sh b/hack/install-cert-manager.sh
index ceebc26db1f..3e07d1251b9 100755
--- a/hack/install-cert-manager.sh
+++ b/hack/install-cert-manager.sh
@@ -54,7 +54,7 @@ source "${REPO_ROOT}/hack/common-vars.sh"
 make --directory="${REPO_ROOT}" "${KUBECTL##*/}"
 
 ## Install cert manager and wait for availability
-"${KUBECTL}" apply -f https://github.com/jetstack/cert-manager/releases/download/v1.14.5/cert-manager.yaml
+"${KUBECTL}" apply -f https://github.com/jetstack/cert-manager/releases/download/v1.15.0/cert-manager.yaml
 "${KUBECTL}" wait --for=condition=Available --timeout=5m -n cert-manager deployment/cert-manager
 "${KUBECTL}" wait --for=condition=Available --timeout=5m -n cert-manager deployment/cert-manager-cainjector
 "${KUBECTL}" wait --for=condition=Available --timeout=5m -n cert-manager deployment/cert-manager-webhook
diff --git a/test/e2e/config/azure-dev.yaml b/test/e2e/config/azure-dev.yaml
index eafcbd97234..6f878c3cb2d 100644
--- a/test/e2e/config/azure-dev.yaml
+++ b/test/e2e/config/azure-dev.yaml
@@ -3,11 +3,11 @@ managementClusterName: capz-e2e
 images:
   - name: ${MANAGER_IMAGE}
     loadBehavior: mustLoad
-  - name: registry.k8s.io/cluster-api/cluster-api-controller:v1.6.5
+  - name: registry.k8s.io/cluster-api/cluster-api-controller:v1.6.6
     loadBehavior: tryLoad
-  - name: registry.k8s.io/cluster-api/kubeadm-bootstrap-controller:v1.6.5
+  - name: registry.k8s.io/cluster-api/kubeadm-bootstrap-controller:v1.6.6
     loadBehavior: tryLoad
-  - name: registry.k8s.io/cluster-api/kubeadm-control-plane-controller:v1.6.5
+  - name: registry.k8s.io/cluster-api/kubeadm-control-plane-controller:v1.6.6
     loadBehavior: tryLoad
   - name: registry.k8s.io/cluster-api-helm/cluster-api-helm-controller:v0.1.1-alpha.1
     loadBehavior: tryLoad
@@ -25,8 +25,8 @@ providers:
           new: --metrics-addr=:8080
       files:
         - sourcePath: "../data/shared/v1beta1/metadata.yaml"
-    - name: v1.6.5
-      value: https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.5/core-components.yaml
+    - name: v1.6.6
+      value: https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.6/core-components.yaml
       type: url
       contract: v1beta1
       files:
@@ -48,8 +48,8 @@ providers:
           new: --metrics-addr=:8080
       files:
         - sourcePath: "../data/shared/v1beta1/metadata.yaml"
-    - name: v1.6.5
-      value: https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.5/bootstrap-components.yaml
+    - name: v1.6.6
+      value: https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.6/bootstrap-components.yaml
       type: url
       contract: v1beta1
       files:
@@ -70,8 +70,8 @@ providers:
           new: --metrics-addr=:8080
       files:
         - sourcePath: "../data/shared/v1beta1/metadata.yaml"
-    - name: v1.6.5
-      value: https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.5/control-plane-components.yaml
+    - name: v1.6.6
+      value: https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.6.6/control-plane-components.yaml
       type: url
       contract: v1beta1
       files: