diff --git a/.chloggen/update-operator-sdk128.yaml b/.chloggen/update-operator-sdk128.yaml
new file mode 100755
index 0000000000..fdbafab104
--- /dev/null
+++ b/.chloggen/update-operator-sdk128.yaml
@@ -0,0 +1,16 @@
+# One of 'breaking', 'deprecation', 'new_component', 'enhancement', 'bug_fix'
+change_type: 'enhancement'
+
+# The name of the component, or a single word describing the area of concern, (e.g. operator, target allocator, github action)
+component: operator
+
+# A brief description of the change. Surround your text with quotes ("") if it needs to start with a backtick (`).
+note: Operator-sdk upgrade to v1.29.0
+
+# One or more tracking issues related to the change
+issues: [1755]
+
+# (Optional) One or more lines of additional information to render under the primary note.
+# These lines will be padded with 2 spaces and then inserted directly into the document.
+# Use pipe (|) for multiline entries.
+subtext:
diff --git a/Makefile b/Makefile
index e08da1a4c5..b448cf282a 100644
--- a/Makefile
+++ b/Makefile
@@ -61,7 +61,7 @@ KUBE_VERSION ?= 1.24
 KIND_CONFIG ?= kind-$(KUBE_VERSION).yaml
 KIND_CLUSTER_NAME ?= "otel-operator"
 
-OPERATOR_SDK_VERSION ?= 1.27.0
+OPERATOR_SDK_VERSION ?= 1.29.0
 
 CERTMANAGER_VERSION ?= 1.10.0
 
@@ -301,7 +301,7 @@ kustomize: ## Download kustomize locally if necessary.
 .PHONY: controller-gen
 controller-gen: $(CONTROLLER_GEN) ## Download controller-gen locally if necessary.
 $(CONTROLLER_GEN): $(LOCALBIN)
-	test -s $(LOCALBIN)/controller-gen || GOBIN=$(LOCALBIN) go install sigs.k8s.io/controller-tools/cmd/controller-gen@$(CONTROLLER_TOOLS_VERSION)
+	test -s $(LOCALBIN)/controller-gen && $(LOCALBIN)/controller-gen --version | grep -q $(CONTROLLER_TOOLS_VERSION) || GOBIN=$(LOCALBIN) go install sigs.k8s.io/controller-tools/cmd/controller-gen@$(CONTROLLER_TOOLS_VERSION)
 
 .PHONY: envtest
 envtest: $(ENVTEST) ## Download envtest-setup locally if necessary.
diff --git a/bundle.Dockerfile b/bundle.Dockerfile
index 63e8863948..af479f2fa4 100644
--- a/bundle.Dockerfile
+++ b/bundle.Dockerfile
@@ -6,7 +6,7 @@ LABEL operators.operatorframework.io.bundle.manifests.v1=manifests/
 LABEL operators.operatorframework.io.bundle.metadata.v1=metadata/
 LABEL operators.operatorframework.io.bundle.package.v1=opentelemetry-operator
 LABEL operators.operatorframework.io.bundle.channels.v1=alpha
-LABEL operators.operatorframework.io.metrics.builder=operator-sdk-v1.27.0
+LABEL operators.operatorframework.io.metrics.builder=operator-sdk-v1.29.0
 LABEL operators.operatorframework.io.metrics.mediatype.v1=metrics+v1
 LABEL operators.operatorframework.io.metrics.project_layout=go.kubebuilder.io/v3
 
diff --git a/bundle/manifests/opentelemetry-operator.clusterserviceversion.yaml b/bundle/manifests/opentelemetry-operator.clusterserviceversion.yaml
index 22d21eaef7..1f1790eef6 100644
--- a/bundle/manifests/opentelemetry-operator.clusterserviceversion.yaml
+++ b/bundle/manifests/opentelemetry-operator.clusterserviceversion.yaml
@@ -31,9 +31,9 @@ metadata:
     categories: Logging & Tracing
     certified: "false"
     containerImage: ghcr.io/open-telemetry/opentelemetry-operator/opentelemetry-operator
-    createdAt: "2023-06-08T08:15:18Z"
+    createdAt: "2023-06-20T11:50:16Z"
     description: Provides the OpenTelemetry components, including the Collector
-    operators.operatorframework.io/builder: operator-sdk-v1.27.0
+    operators.operatorframework.io/builder: operator-sdk-v1.29.0
     operators.operatorframework.io/project_layout: go.kubebuilder.io/v3
     repository: github.com/open-telemetry/opentelemetry-operator
     support: OpenTelemetry Community
@@ -339,7 +339,7 @@ spec:
                 - --upstream=http://127.0.0.1:8080/
                 - --logtostderr=true
                 - --v=0
-                image: gcr.io/kubebuilder/kube-rbac-proxy:v0.13.0
+                image: gcr.io/kubebuilder/kube-rbac-proxy:v0.13.1
                 name: kube-rbac-proxy
                 ports:
                 - containerPort: 8443
diff --git a/bundle/metadata/annotations.yaml b/bundle/metadata/annotations.yaml
index 611c316083..b0f3b46044 100644
--- a/bundle/metadata/annotations.yaml
+++ b/bundle/metadata/annotations.yaml
@@ -5,7 +5,7 @@ annotations:
   operators.operatorframework.io.bundle.metadata.v1: metadata/
   operators.operatorframework.io.bundle.package.v1: opentelemetry-operator
   operators.operatorframework.io.bundle.channels.v1: alpha
-  operators.operatorframework.io.metrics.builder: operator-sdk-v1.27.0
+  operators.operatorframework.io.metrics.builder: operator-sdk-v1.29.0
   operators.operatorframework.io.metrics.mediatype.v1: metrics+v1
   operators.operatorframework.io.metrics.project_layout: go.kubebuilder.io/v3
 
diff --git a/config/default/manager_auth_proxy_patch.yaml b/config/default/manager_auth_proxy_patch.yaml
index 126a4ad431..80999a45ab 100644
--- a/config/default/manager_auth_proxy_patch.yaml
+++ b/config/default/manager_auth_proxy_patch.yaml
@@ -10,7 +10,7 @@ spec:
     spec:
       containers:
       - name: kube-rbac-proxy
-        image: gcr.io/kubebuilder/kube-rbac-proxy:v0.13.0
+        image: gcr.io/kubebuilder/kube-rbac-proxy:v0.13.1
         args:
         - "--secure-listen-address=0.0.0.0:8443"
         - "--upstream=http://127.0.0.1:8080/"