diff --git a/changelog/fragments/helm-ansible-download-makefile.yaml b/changelog/fragments/helm-ansible-download-makefile.yaml
new file mode 100644
index 0000000000..7de2f2cb41
--- /dev/null
+++ b/changelog/fragments/helm-ansible-download-makefile.yaml
@@ -0,0 +1,18 @@
+entries:
+  - description: >
+      Corrected the download URL for helm-operator and ansible-operator in their respective project types.
+    kind: bugfix
+    migration:
+      header: For Helm and Ansible projects, fix the helm-operator and ansible-operator URLs in the Makefile
+      body: >
+        Helm projects: `https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/helm-operator-v1.3.0-$(ARCHOPER)-$(OSOPER)`
+        -> `https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/helm-operator_$(OS)_$(ARCH)`
+        Ansible projects: `https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/ansible-operator-v1.3.0-$(ARCHOPER)-$(OSOPER)`
+        -> `https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/ansible-operator_$(OS)_$(ARCH)`
+  - description: >
+      Fixed the order of helm-operator, ansible-operator, and kustomize binary checks in the Makefile.
+    kind: bugfix
+    migration:
+      header: For Helm and Ansible projects, fix the helm-operator, ansible-operator, and kustomize Makefile rules
+      body: >
+        See the diff in [this PR](https://github.com/operator-framework/operator-sdk/pull/4407) for details.
diff --git a/internal/plugins/ansible/v1/scaffolds/internal/templates/makefile.go b/internal/plugins/ansible/v1/scaffolds/internal/templates/makefile.go
index 2a927b26fa..fcf32617f4 100644
--- a/internal/plugins/ansible/v1/scaffolds/internal/templates/makefile.go
+++ b/internal/plugins/ansible/v1/scaffolds/internal/templates/makefile.go
@@ -101,34 +101,40 @@ docker-push:
 
 PATH  := $(PATH):$(PWD)/bin
 SHELL := env PATH=$(PATH) /bin/sh
-OS    = $(shell uname -s | tr '[:upper:]' '[:lower:]')
-ARCH  = $(shell uname -m | sed 's/x86_64/amd64/')
-OSOPER   = $(shell uname -s | tr '[:upper:]' '[:lower:]' | sed 's/darwin/apple-darwin/' | sed 's/linux/linux-gnu/')
-ARCHOPER = $(shell uname -m )
+OS := $(shell uname -s | tr '[:upper:]' '[:lower:]')
+ARCH := $(shell uname -m | sed 's/x86_64/amd64/')
 
+# Download kustomize locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: kustomize
+KUSTOMIZE = $(shell pwd)/bin/kustomize
 kustomize:
-ifeq (, $(shell which kustomize 2>/dev/null))
+ifeq (,$(wildcard $(KUSTOMIZE)))
+ifeq (,$(shell which kustomize 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/{{ .KustomizeVersion }}/kustomize_{{ .KustomizeVersion }}_$(OS)_$(ARCH).tar.gz | tar xzf - -C bin/ ;\
+	mkdir -p $(dir $(KUSTOMIZE)) ;\
+	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/{{ .KustomizeVersion }}/kustomize_{{ .KustomizeVersion }}_$(OS)_$(ARCH).tar.gz | \
+	tar xzf - -C bin/ ;\
 	}
-KUSTOMIZE=$(realpath ./bin/kustomize)
 else
-KUSTOMIZE=$(shell which kustomize)
+KUSTOMIZE = $(shell which kustomize)
+endif
 endif
 
+# Download ansible-operator locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: ansible-operator
+ANSIBLE_OPERATOR = $(shell pwd)/bin/ansible-operator
 ansible-operator:
-ifeq (, $(shell which ansible-operator 2>/dev/null))
+ifeq (,$(wildcard $(ANSIBLE_OPERATOR)))
+ifeq (,$(shell which ansible-operator 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -LO https://github.com/operator-framework/operator-sdk/releases/download/{{ .AnsibleOperatorVersion}}/ansible-operator-{{ .AnsibleOperatorVersion}}-$(ARCHOPER)-$(OSOPER) ;\
-	mv ansible-operator-{{ .AnsibleOperatorVersion}}-$(ARCHOPER)-$(OSOPER) ./bin/ansible-operator ;\
-	chmod +x ./bin/ansible-operator ;\
+	mkdir -p $(dir $(ANSIBLE_OPERATOR)) ;\
+	curl -sSLo $(ANSIBLE_OPERATOR) https://github.com/operator-framework/operator-sdk/releases/download/{{ .AnsibleOperatorVersion }}/ansible-operator_$(OS)_$(ARCH) ;\
+	chmod +x $(ANSIBLE_OPERATOR) ;\
 	}
-ANSIBLE_OPERATOR=$(realpath ./bin/ansible-operator)
 else
-ANSIBLE_OPERATOR=$(shell which ansible-operator)
+ANSIBLE_OPERATOR = $(shell which ansible-operator)
+endif
 endif
 `
diff --git a/internal/plugins/helm/v1/scaffolds/internal/templates/makefile.go b/internal/plugins/helm/v1/scaffolds/internal/templates/makefile.go
index f5af0f1039..c530b16970 100644
--- a/internal/plugins/helm/v1/scaffolds/internal/templates/makefile.go
+++ b/internal/plugins/helm/v1/scaffolds/internal/templates/makefile.go
@@ -101,34 +101,40 @@ docker-push:
 
 PATH  := $(PATH):$(PWD)/bin
 SHELL := env PATH=$(PATH) /bin/sh
-OS    = $(shell uname -s | tr '[:upper:]' '[:lower:]')
-ARCH  = $(shell uname -m | sed 's/x86_64/amd64/')
-OSOPER   = $(shell uname -s | tr '[:upper:]' '[:lower:]' | sed 's/darwin/apple-darwin/' | sed 's/linux/linux-gnu/')
-ARCHOPER = $(shell uname -m )
+OS := $(shell uname -s | tr '[:upper:]' '[:lower:]')
+ARCH := $(shell uname -m | sed 's/x86_64/amd64/')
 
+# Download kustomize locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: kustomize
+KUSTOMIZE = $(shell pwd)/bin/kustomize
 kustomize:
-ifeq (, $(shell which kustomize 2>/dev/null))
+ifeq (,$(wildcard $(KUSTOMIZE)))
+ifeq (,$(shell which kustomize 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/{{ .KustomizeVersion }}/kustomize_{{ .KustomizeVersion }}_$(OS)_$(ARCH).tar.gz | tar xzf - -C bin/ ;\
+	mkdir -p $(dir $(KUSTOMIZE)) ;\
+	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/{{ .KustomizeVersion }}/kustomize_{{ .KustomizeVersion }}_$(OS)_$(ARCH).tar.gz | \
+	tar xzf - -C bin/ ;\
 	}
-KUSTOMIZE=$(realpath ./bin/kustomize)
 else
-KUSTOMIZE=$(shell which kustomize)
+KUSTOMIZE = $(shell which kustomize)
+endif
 endif
 
+# Download helm-operator locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: helm-operator
+HELM_OPERATOR = $(shell pwd)/bin/helm-operator
 helm-operator:
-ifeq (, $(shell which helm-operator 2>/dev/null))
+ifeq (,$(wildcard $(HELM_OPERATOR)))
+ifeq (,$(shell which helm-operator 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -LO https://github.com/operator-framework/operator-sdk/releases/download/{{ .HelmOperatorVersion }}/helm-operator-{{ .HelmOperatorVersion }}-$(ARCHOPER)-$(OSOPER) ;\
-	mv helm-operator-{{ .HelmOperatorVersion }}-$(ARCHOPER)-$(OSOPER) ./bin/helm-operator ;\
-	chmod +x ./bin/helm-operator ;\
+	mkdir -p $(dir $(HELM_OPERATOR)) ;\
+	curl -sSLo $(HELM_OPERATOR) https://github.com/operator-framework/operator-sdk/releases/download/{{ .HelmOperatorVersion }}/helm-operator_$(OS)_$(ARCH) ;\
+	chmod +x $(HELM_OPERATOR) ;\
 	}
-HELM_OPERATOR=$(realpath ./bin/helm-operator)
 else
-HELM_OPERATOR=$(shell which helm-operator)
+HELM_OPERATOR = $(shell which helm-operator)
+endif
 endif
 `
diff --git a/testdata/ansible/memcached-operator/Makefile b/testdata/ansible/memcached-operator/Makefile
index 3aeddf1d18..ae19e3034d 100644
--- a/testdata/ansible/memcached-operator/Makefile
+++ b/testdata/ansible/memcached-operator/Makefile
@@ -47,35 +47,41 @@ docker-push:
 
 PATH  := $(PATH):$(PWD)/bin
 SHELL := env PATH=$(PATH) /bin/sh
-OS    = $(shell uname -s | tr '[:upper:]' '[:lower:]')
-ARCH  = $(shell uname -m | sed 's/x86_64/amd64/')
-OSOPER   = $(shell uname -s | tr '[:upper:]' '[:lower:]' | sed 's/darwin/apple-darwin/' | sed 's/linux/linux-gnu/')
-ARCHOPER = $(shell uname -m )
+OS := $(shell uname -s | tr '[:upper:]' '[:lower:]')
+ARCH := $(shell uname -m | sed 's/x86_64/amd64/')
 
+# Download kustomize locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: kustomize
+KUSTOMIZE = $(shell pwd)/bin/kustomize
 kustomize:
-ifeq (, $(shell which kustomize 2>/dev/null))
+ifeq (,$(wildcard $(KUSTOMIZE)))
+ifeq (,$(shell which kustomize 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/v3.5.4/kustomize_v3.5.4_$(OS)_$(ARCH).tar.gz | tar xzf - -C bin/ ;\
+	mkdir -p $(dir $(KUSTOMIZE)) ;\
+	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/v3.5.4/kustomize_v3.5.4_$(OS)_$(ARCH).tar.gz | \
+	tar xzf - -C bin/ ;\
 	}
-KUSTOMIZE=$(realpath ./bin/kustomize)
 else
-KUSTOMIZE=$(shell which kustomize)
+KUSTOMIZE = $(shell which kustomize)
+endif
 endif
 
+# Download ansible-operator locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: ansible-operator
+ANSIBLE_OPERATOR = $(shell pwd)/bin/ansible-operator
 ansible-operator:
-ifeq (, $(shell which ansible-operator 2>/dev/null))
+ifeq (,$(wildcard $(ANSIBLE_OPERATOR)))
+ifeq (,$(shell which ansible-operator 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -LO https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/ansible-operator-v1.3.0-$(ARCHOPER)-$(OSOPER) ;\
-	mv ansible-operator-v1.3.0-$(ARCHOPER)-$(OSOPER) ./bin/ansible-operator ;\
-	chmod +x ./bin/ansible-operator ;\
+	mkdir -p $(dir $(ANSIBLE_OPERATOR)) ;\
+	curl -sSLo $(ANSIBLE_OPERATOR) https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/ansible-operator_$(OS)_$(ARCH) ;\
+	chmod +x $(ANSIBLE_OPERATOR) ;\
 	}
-ANSIBLE_OPERATOR=$(realpath ./bin/ansible-operator)
 else
-ANSIBLE_OPERATOR=$(shell which ansible-operator)
+ANSIBLE_OPERATOR = $(shell which ansible-operator)
+endif
 endif
 
 # Generate bundle manifests and metadata, then validate generated files.
diff --git a/testdata/helm/memcached-operator/Makefile b/testdata/helm/memcached-operator/Makefile
index 4fdc5c786e..f0fd1f98c8 100644
--- a/testdata/helm/memcached-operator/Makefile
+++ b/testdata/helm/memcached-operator/Makefile
@@ -47,35 +47,41 @@ docker-push:
 
 PATH  := $(PATH):$(PWD)/bin
 SHELL := env PATH=$(PATH) /bin/sh
-OS    = $(shell uname -s | tr '[:upper:]' '[:lower:]')
-ARCH  = $(shell uname -m | sed 's/x86_64/amd64/')
-OSOPER   = $(shell uname -s | tr '[:upper:]' '[:lower:]' | sed 's/darwin/apple-darwin/' | sed 's/linux/linux-gnu/')
-ARCHOPER = $(shell uname -m )
+OS := $(shell uname -s | tr '[:upper:]' '[:lower:]')
+ARCH := $(shell uname -m | sed 's/x86_64/amd64/')
 
+# Download kustomize locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: kustomize
+KUSTOMIZE = $(shell pwd)/bin/kustomize
 kustomize:
-ifeq (, $(shell which kustomize 2>/dev/null))
+ifeq (,$(wildcard $(KUSTOMIZE)))
+ifeq (,$(shell which kustomize 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/v3.5.4/kustomize_v3.5.4_$(OS)_$(ARCH).tar.gz | tar xzf - -C bin/ ;\
+	mkdir -p $(dir $(KUSTOMIZE)) ;\
+	curl -sSLo - https://github.com/kubernetes-sigs/kustomize/releases/download/kustomize/v3.5.4/kustomize_v3.5.4_$(OS)_$(ARCH).tar.gz | \
+	tar xzf - -C bin/ ;\
 	}
-KUSTOMIZE=$(realpath ./bin/kustomize)
 else
-KUSTOMIZE=$(shell which kustomize)
+KUSTOMIZE = $(shell which kustomize)
+endif
 endif
 
+# Download helm-operator locally if necessary, preferring the $(pwd)/bin path over global if both exist.
+.PHONY: helm-operator
+HELM_OPERATOR = $(shell pwd)/bin/helm-operator
 helm-operator:
-ifeq (, $(shell which helm-operator 2>/dev/null))
+ifeq (,$(wildcard $(HELM_OPERATOR)))
+ifeq (,$(shell which helm-operator 2>/dev/null))
 	@{ \
 	set -e ;\
-	mkdir -p bin ;\
-	curl -LO https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/helm-operator-v1.3.0-$(ARCHOPER)-$(OSOPER) ;\
-	mv helm-operator-v1.3.0-$(ARCHOPER)-$(OSOPER) ./bin/helm-operator ;\
-	chmod +x ./bin/helm-operator ;\
+	mkdir -p $(dir $(HELM_OPERATOR)) ;\
+	curl -sSLo $(HELM_OPERATOR) https://github.com/operator-framework/operator-sdk/releases/download/v1.3.0/helm-operator_$(OS)_$(ARCH) ;\
+	chmod +x $(HELM_OPERATOR) ;\
 	}
-HELM_OPERATOR=$(realpath ./bin/helm-operator)
 else
-HELM_OPERATOR=$(shell which helm-operator)
+HELM_OPERATOR = $(shell which helm-operator)
+endif
 endif
 
 # Generate bundle manifests and metadata, then validate generated files.