diff --git a/.go-tools b/.go-tools
index 7abfaaa35..3cd711755 100644
--- a/.go-tools
+++ b/.go-tools
@@ -1,6 +1,6 @@
 github.com/oligot/go-mod-upgrade@v0.9.1
 github.com/segmentio/golines@v0.11.0
 gotest.tools/gotestsum@v1.9.0
-sigs.k8s.io/controller-runtime/tools/setup-envtest@v0.0.0-20230131195449-5db173878d6d
-github.com/google/go-containerregistry/cmd/crane@v0.12.1
-github.com/drone/envsubst/cmd/envsubst@v1.0.3 # FREEZE
+sigs.k8s.io/controller-runtime/tools/setup-envtest@v0.0.0-20230208013708-22718275bffe
+github.com/google/go-containerregistry/cmd/crane@v0.13.0
+github.com/drone/envsubst/cmd/envsubst@v1.0.3
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index b05ccb518..4d160281a 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -97,7 +97,7 @@ repos:
       - --comment-style
       - <!--|| -->
 - repo: https://github.com/norwoodj/helm-docs
-  rev: v1.2.0
+  rev: v1.11.0
   hooks:
   - id: helm-docs
     stages: [commit]
diff --git a/.tool-versions b/.tool-versions
index bf5202a79..ebed101ae 100644
--- a/.tool-versions
+++ b/.tool-versions
@@ -1,18 +1,17 @@
 clusterctl 1.3.3
 flux2 0.39.0
-gcloud 416.0.0
-gcloud 416.0.0
+gcloud 417.0.1
 ginkgo 2.8.0
 gojq 0.12.11
 golang 1.20
-golangci-lint 1.51.0
-goreleaser 1.15.0
-helm 3.11.0
+golangci-lint 1.51.1
+goreleaser 1.15.2
+helm 3.11.1
 helm-docs 1.11.0
 kind 0.17.0
-kube-controller-tools 0.11.2
+kube-controller-tools 0.11.3
 kubectl 1.26.1
-kustomize 4.5.7
-pre-commit 3.0.2
+kustomize 5.0.0
+pre-commit 3.0.4
 shfmt 3.6.0
 upx 4.0.2
diff --git a/Dockerfile b/Dockerfile
index 46d445611..bb3df461a 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -3,8 +3,8 @@
 # Copyright 2023 D2iQ, Inc. All rights reserved.
 # SPDX-License-Identifier: Apache-2.0
 
-FROM --platform=linux/amd64 gcr.io/distroless/static@sha256:93bb1b564033909a660111671303f9683e13f0567de95e4b6fde3226e532955e as linux-amd64
-FROM --platform=linux/arm64 gcr.io/distroless/static@sha256:72fec9960c247e7e68ed1db4b5b561f6b6da437215fb41d5fd7df790ec6df1a7 as linux-arm64
+FROM --platform=linux/amd64 gcr.io/distroless/static@sha256:b1a9ecc1b37ec3bc9a2d8f8a0a5090ee5babda422f2b1c3724f108fa7e506e77 as linux-amd64
+FROM --platform=linux/arm64 gcr.io/distroless/static@sha256:2fc464bd828a7f713020c06f0bb4ff01670d08292ba4a01ffbc3b56a1d59da3a as linux-arm64
 
 FROM --platform=linux/${TARGETARCH} linux-${TARGETARCH}
 
diff --git a/make/tools.mk b/make/tools.mk
index eeb0dd719..5d81feb54 100644
--- a/make/tools.mk
+++ b/make/tools.mk
@@ -80,8 +80,18 @@ upgrade-tools: upgrade-go-tools; $(info $(M) upgrading all tools to latest avail
 upgrade-go-tools: ## Upgrades all go tools to latest available versions
 upgrade-go-tools: install-tool.golang; $(info $(M) upgrading all go tools to latest available versions)
 	grep -v '# FREEZE' .go-tools | \
-		grep -Eo '^[^#]\S+' | \
-		sed 's/@.\+$$/@latest/' | \
-			xargs -I {} bash -ec '\
-				export LATEST_VERSION=$$(go list -m {}) && \
-				sed -i "s|$${LATEST_VERSION%% *}@.\+$$|$${LATEST_VERSION/ /@}|" .go-tools'
+		grep -Eo '^[^#][^@]+' | \
+			xargs -I {} bash -ec ' \
+				original_module_path={}; \
+				module_path={}; \
+				while [ "$${module_path}" != "." ]; do \
+					LATEST_VERSION=$$(go list -m $${module_path}@latest 2>/dev/null || echo ""); \
+					if [ -n "$${LATEST_VERSION}" ]; then \
+						sed -i "s|$${original_module_path}@.\+$$|$${original_module_path}@$${LATEST_VERSION#* }|" .go-tools; \
+						exit; \
+					else \
+						module_path=$$(dirname $${module_path}); \
+					fi; \
+				done; \
+				echo "Failed to find latest module version for $${original_module_path}"; \
+				exit 1'