diff --git a/Makefile b/Makefile
index cf8a84ff571a9..0e36e67d9e74a 100644
--- a/Makefile
+++ b/Makefile
@@ -1543,8 +1543,7 @@ derive:
 .PHONY: derive-up-to-date
 derive-up-to-date: must-start-clean/host derive
 	@if ! git diff --quiet; then \
-		echo 'Please run make derive.'; \
-		git diff; \
+		./build.assets/tooling/cmd/please-run.sh "derived functions" "make derive"; \
 		exit 1; \
 	fi
 
@@ -1579,16 +1578,14 @@ endif
 .PHONY: protos-up-to-date/host
 protos-up-to-date/host: must-start-clean/host grpc/host
 	@if ! git diff --quiet; then \
-		echo 'Please run make grpc.'; \
-		git diff; \
+		./build.assets/tooling/cmd/please-run.sh "protos gRPC" "make grpc"; \
 		exit 1; \
 	fi
 
 .PHONY: must-start-clean/host
 must-start-clean/host:
 	@if ! git diff --quiet; then \
-		echo 'This must be run from a repo with no unstaged commits.'; \
-		git diff; \
+		./build.assets/tooling/cmd/please-run.sh "protos gRPC" "make grpc"; \
 		exit 1; \
 	fi
 
@@ -1597,14 +1594,12 @@ must-start-clean/host:
 crds-up-to-date: must-start-clean/host
 	$(MAKE) -C integrations/operator manifests
 	@if ! git diff --quiet; then \
-		echo 'Please run make -C integrations/operator manifests.'; \
-		git diff; \
+		./build.assets/tooling/cmd/please-run.sh "operator CRD manifests" "make -C integrations/operator crd"; \
 		exit 1; \
 	fi
 	$(MAKE) -C integrations/operator crd-docs
 	@if ! git diff --quiet; then \
-		echo 'Please run make -C integrations/operator crd-docs.'; \
-		git diff; \
+		./build.assets/tooling/cmd/please-run.sh "operator CRD docs" "make -C integrations/operator crd"; \
 		exit 1; \
 	fi
 
@@ -1613,8 +1608,7 @@ crds-up-to-date: must-start-clean/host
 terraform-resources-up-to-date: must-start-clean/host
 	$(MAKE) -C integrations/terraform docs
 	@if ! git diff --quiet; then \
-		echo 'Please run make -C integrations/terraform docs.'; \
-		git diff; \
+		./build.assets/tooling/cmd/please-run.sh "TF provider docs" "make -C integrations/terraform docs"; \
 		exit 1; \
 	fi
 
diff --git a/api/proto/teleport/accesslist/v1/accesslist.proto b/api/proto/teleport/accesslist/v1/accesslist.proto
index 373c325027d39..0b8211b75f627 100644
--- a/api/proto/teleport/accesslist/v1/accesslist.proto
+++ b/api/proto/teleport/accesslist/v1/accesslist.proto
@@ -64,6 +64,8 @@ message AccessListSpec {
   AccessListRequires ownership_requires = 5;
 
   // grants describes the access granted by membership to this Access List.
+  // This is a totally new comment
+  // And I forgot to run the generation commands.
   AccessListGrants grants = 6;
 
   // title is a plaintext short description of the Access List.
diff --git a/build.assets/tooling/cmd/please-run.sh b/build.assets/tooling/cmd/please-run.sh
new file mode 100755
index 0000000000000..c58f29d836cff
--- /dev/null
+++ b/build.assets/tooling/cmd/please-run.sh
@@ -0,0 +1,40 @@
+#!/usr/bin/env sh
+
+# This script is a helper that tells developers what generated content is out of date
+# and which command to run.
+# When running on GitHub actions, the script will also create an error in the PR and
+# collapse the diff to improve readability.
+
+set -eu
+
+KIND="$1"
+GENERATE_COMMAND="$2"
+
+TITLE="$KIND are out-of-date"
+MESSAGE="Please run the command \`$GENERATE_COMMAND\`"
+
+if [ -z ${GITHUB_ACTIONS+x} ];
+then
+    # We are not in GitHub Actions
+    echo "============="
+    echo "$TITLE"
+    echo "$MESSAGE"
+    echo "============="
+
+    git diff || true
+else
+    # We are in GitHub Actions
+
+    # Create a GitHub error
+    echo "::error file=Makefile,title=$TITLE::$MESSAGE"
+
+    # Also write to the job logs
+    echo "============="
+    echo "$TITLE"
+    echo "$MESSAGE"
+    echo "============="
+
+    echo "::group::Diff output"
+    git diff || true
+    echo "::endgroup::"
+fi
\ No newline at end of file
diff --git a/integrations/operator/Makefile b/integrations/operator/Makefile
index 145a7c97dd9b1..4b8b07247e847 100644
--- a/integrations/operator/Makefile
+++ b/integrations/operator/Makefile
@@ -72,6 +72,9 @@ help: ## Display this help.
 
 ##@ Development
 
+.PHONY: crd ## Single command to generate anything CRD-related (manifests and docs)
+crd: crdgen crd-docs
+
 .PHONY: crdgen
 crdgen: ## Generate CRDs
 	make -C crdgen