diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index 1284c0374cb34..e5180b037a916 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -271,6 +271,15 @@ jobs:
         # coderd/rbac/object_gen.go:1:1: syntax error: package statement must be first
         run: "make --output-sync -B gen"
 
+      - name: make update-golden-files
+        run: |
+          make clean/golden-files
+          # Notifications require DB, we could start a DB instance here but
+          # let's just restore for now.
+          git checkout -- coderd/notifications/testdata/rendered-templates
+          # As above, skip `-j` flag.
+          make --output-sync -B update-golden-files
+
       - name: Check for unstaged files
         run: ./scripts/check_unstaged.sh
 
diff --git a/Makefile b/Makefile
index 6ce22a9a4ea50..bc109983ca695 100644
--- a/Makefile
+++ b/Makefile
@@ -702,18 +702,33 @@ coderd/apidoc/swagger.json: $(shell find ./scripts/apidocgen $(FIND_EXCLUSIONS)
 
 update-golden-files: \
 	cli/testdata/.gen-golden \
-	helm/coder/tests/testdata/.gen-golden \
-	helm/provisioner/tests/testdata/.gen-golden \
-	enterprise/cli/testdata/.gen-golden \
-	enterprise/tailnet/testdata/.gen-golden \
-	tailnet/testdata/.gen-golden \
 	coderd/.gen-golden \
 	coderd/notifications/.gen-golden \
-	provisioner/terraform/testdata/.gen-golden
+	enterprise/cli/testdata/.gen-golden \
+	enterprise/tailnet/testdata/.gen-golden \
+	helm/coder/tests/testdata/.gen-golden \
+	helm/provisioner/tests/testdata/.gen-golden \
+	provisioner/terraform/testdata/.gen-golden \
+	tailnet/testdata/.gen-golden
 .PHONY: update-golden-files
 
+clean/golden-files:
+	find . -type f -name '.gen-golden' -delete
+	find \
+		cli/testdata \
+		coderd/notifications/testdata \
+		coderd/testdata \
+		enterprise/cli/testdata \
+		enterprise/tailnet/testdata \
+		helm/coder/tests/testdata \
+		helm/provisioner/tests/testdata \
+		provisioner/terraform/testdata \
+		tailnet/testdata \
+		-type f -name '*.golden' -delete
+.PHONY: clean/golden-files
+
 cli/testdata/.gen-golden: $(wildcard cli/testdata/*.golden) $(wildcard cli/*.tpl) $(GO_SRC_FILES) $(wildcard cli/*_test.go)
-	go test ./cli -run="Test(CommandHelp|ServerYAML|ErrorExamples)" -update
+	go test ./cli -run="Test(CommandHelp|ServerYAML|ErrorExamples|.*Golden)" -update
 	touch "$@"
 
 enterprise/cli/testdata/.gen-golden: $(wildcard enterprise/cli/testdata/*.golden) $(wildcard cli/*.tpl) $(GO_SRC_FILES) $(wildcard enterprise/cli/*_test.go)
diff --git a/cli/testdata/coder_templates_plan_--help.golden b/cli/testdata/coder_templates_plan_--help.golden
deleted file mode 100644
index 0085c37238e34..0000000000000
--- a/cli/testdata/coder_templates_plan_--help.golden
+++ /dev/null
@@ -1,6 +0,0 @@
-Usage: coder templates plan <directory>
-
-Plan a template push from the current directory
-
----
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_provisionerd_--help.golden b/enterprise/cli/testdata/coder_provisionerd_--help.golden
deleted file mode 100644
index 7209d4962abac..0000000000000
--- a/enterprise/cli/testdata/coder_provisionerd_--help.golden
+++ /dev/null
@@ -1,15 +0,0 @@
-coder v0.0.0-devel
-
-USAGE:
-  coder provisionerd
-
-  Manage provisioner daemons
-
-  Aliases: provisioner
-
-SUBCOMMANDS:
-    keys     Manage provisioner keys
-    start    Run a provisioner daemon
-
-———
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_provisionerd_keys_--help.golden b/enterprise/cli/testdata/coder_provisionerd_keys_--help.golden
deleted file mode 100644
index 38feaec6dc4a8..0000000000000
--- a/enterprise/cli/testdata/coder_provisionerd_keys_--help.golden
+++ /dev/null
@@ -1,16 +0,0 @@
-coder v0.0.0-devel
-
-USAGE:
-  coder provisionerd keys
-
-  Manage provisioner keys
-
-  Aliases: key
-
-SUBCOMMANDS:
-    create    Create a new provisioner key
-    delete    Delete a provisioner key
-    list      List provisioner keys in an organization
-
-———
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_provisionerd_keys_create_--help.golden b/enterprise/cli/testdata/coder_provisionerd_keys_create_--help.golden
deleted file mode 100644
index 8f70eb7184e5d..0000000000000
--- a/enterprise/cli/testdata/coder_provisionerd_keys_create_--help.golden
+++ /dev/null
@@ -1,16 +0,0 @@
-coder v0.0.0-devel
-
-USAGE:
-  coder provisionerd keys create [flags] <name>
-
-  Create a new provisioner key
-
-OPTIONS:
-  -O, --org string, $CODER_ORGANIZATION
-          Select which organization (uuid or name) to use.
-
-  -t, --tag string-array, $CODER_PROVISIONERD_TAGS
-          Tags to filter provisioner jobs by.
-
-———
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_provisionerd_keys_delete_--help.golden b/enterprise/cli/testdata/coder_provisionerd_keys_delete_--help.golden
deleted file mode 100644
index 0ab277f6609e7..0000000000000
--- a/enterprise/cli/testdata/coder_provisionerd_keys_delete_--help.golden
+++ /dev/null
@@ -1,18 +0,0 @@
-coder v0.0.0-devel
-
-USAGE:
-  coder provisionerd keys delete [flags] <name>
-
-  Delete a provisioner key
-
-  Aliases: rm
-
-OPTIONS:
-  -O, --org string, $CODER_ORGANIZATION
-          Select which organization (uuid or name) to use.
-
-  -y, --yes bool
-          Bypass prompts.
-
-———
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_provisionerd_keys_list_--help.golden b/enterprise/cli/testdata/coder_provisionerd_keys_list_--help.golden
deleted file mode 100644
index 8e5c48f0cd457..0000000000000
--- a/enterprise/cli/testdata/coder_provisionerd_keys_list_--help.golden
+++ /dev/null
@@ -1,15 +0,0 @@
-coder v0.0.0-devel
-
-USAGE:
-  coder provisionerd keys list [flags]
-
-  List provisioner keys in an organization
-
-  Aliases: ls
-
-OPTIONS:
-  -O, --org string, $CODER_ORGANIZATION
-          Select which organization (uuid or name) to use.
-
-———
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_provisionerd_start_--help.golden b/enterprise/cli/testdata/coder_provisionerd_start_--help.golden
deleted file mode 100644
index 169b7fca2520c..0000000000000
--- a/enterprise/cli/testdata/coder_provisionerd_start_--help.golden
+++ /dev/null
@@ -1,55 +0,0 @@
-coder v0.0.0-devel
-
-USAGE:
-  coder provisionerd start [flags]
-
-  Run a provisioner daemon
-
-OPTIONS:
-  -O, --org string, $CODER_ORGANIZATION
-          Select which organization (uuid or name) to use.
-
-  -c, --cache-dir string, $CODER_CACHE_DIRECTORY (default: [cache dir])
-          Directory to store cached data.
-
-      --log-filter string-array, $CODER_PROVISIONER_DAEMON_LOG_FILTER
-          Filter debug logs by matching against a given regex. Use .* to match
-          all debug logs.
-
-      --log-human string, $CODER_PROVISIONER_DAEMON_LOGGING_HUMAN (default: /dev/stderr)
-          Output human-readable logs to a given file.
-
-      --log-json string, $CODER_PROVISIONER_DAEMON_LOGGING_JSON
-          Output JSON logs to a given file.
-
-      --log-stackdriver string, $CODER_PROVISIONER_DAEMON_LOGGING_STACKDRIVER
-          Output Stackdriver compatible logs to a given file.
-
-      --name string, $CODER_PROVISIONER_DAEMON_NAME
-          Name of this provisioner daemon. Defaults to the current hostname
-          without FQDN.
-
-      --poll-interval duration, $CODER_PROVISIONERD_POLL_INTERVAL (default: 1s)
-          Deprecated and ignored.
-
-      --poll-jitter duration, $CODER_PROVISIONERD_POLL_JITTER (default: 100ms)
-          Deprecated and ignored.
-
-      --prometheus-address string, $CODER_PROMETHEUS_ADDRESS (default: 127.0.0.1:2112)
-          The bind address to serve prometheus metrics.
-
-      --prometheus-enable bool, $CODER_PROMETHEUS_ENABLE (default: false)
-          Serve prometheus metrics on the address defined by prometheus address.
-
-      --psk string, $CODER_PROVISIONER_DAEMON_PSK
-          Pre-shared key to authenticate with Coder server.
-          DEPRECATED: Use --key instead.
-
-  -t, --tag string-array, $CODER_PROVISIONERD_TAGS
-          Tags to filter provisioner jobs by.
-
-      --verbose bool, $CODER_PROVISIONER_DAEMON_VERBOSE (default: false)
-          Output debug-level logs.
-
-———
-Run `coder --help` for a list of global options.
diff --git a/enterprise/cli/testdata/coder_wsproxy_--help.golden b/enterprise/cli/testdata/coder_wsproxy_--help.golden
deleted file mode 100644
index 8f39caa1ecd9e..0000000000000
--- a/enterprise/cli/testdata/coder_wsproxy_--help.golden
+++ /dev/null
@@ -1,17 +0,0 @@
-Usage: coder workspace-proxy
-
-Manage workspace proxies
-
-Aliases: wsproxy
-
-Subcommands
-    create              Create a workspace proxy
-    delete              Delete a workspace proxy
-    edit                Edit a workspace proxy
-    ls                  List all workspace proxies
-    regenerate-token    Regenerate a workspace proxy authentication token. This
-                        will invalidate the existing authentication token.
-    server              Start a workspace proxy server
-
----
-Run `coder --help` for a list of global options.
diff --git a/helm/provisioner/tests/chart_test.go b/helm/provisioner/tests/chart_test.go
index 0c27771ce369a..136e77f76a4ab 100644
--- a/helm/provisioner/tests/chart_test.go
+++ b/helm/provisioner/tests/chart_test.go
@@ -121,6 +121,7 @@ func TestRenderChart(t *testing.T) {
 	helmPath := lookupHelm(t)
 	err := updateHelmDependencies(t, helmPath, "..")
 	require.NoError(t, err, "failed to build Helm dependencies")
+
 	for _, tc := range testCases {
 		tc := tc
 		t.Run(tc.name, func(t *testing.T) {
@@ -162,6 +163,9 @@ func TestUpdateGoldenFiles(t *testing.T) {
 	}
 
 	helmPath := lookupHelm(t)
+	err := updateHelmDependencies(t, helmPath, "..")
+	require.NoError(t, err, "failed to build Helm dependencies")
+
 	for _, tc := range testCases {
 		if tc.expectedError != "" {
 			t.Logf("skipping test case %q with render error", tc.name)
@@ -171,7 +175,8 @@ func TestUpdateGoldenFiles(t *testing.T) {
 		valuesPath := tc.valuesFilePath()
 		templateOutput, err := runHelmTemplate(t, helmPath, "..", valuesPath)
 		if err != nil {
-			t.Logf("Command output:\n%s", templateOutput)
+			t.Logf("error running `helm template -f %q`: %v", valuesPath, err)
+			t.Logf("output: %s", templateOutput)
 		}
 		require.NoError(t, err, "failed to run `helm template -f %q`", valuesPath)
 

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