diff --git a/cli/server_test.go b/cli/server_test.go
index 83a7f7171c6f5..9cf466c6c35aa 100644
--- a/cli/server_test.go
+++ b/cli/server_test.go
@@ -1620,6 +1620,39 @@ func TestServer_Production(t *testing.T) {
 	require.NoError(t, err)
 }
 
+//nolint:tparallel,paralleltest // This test sets environment variables.
+func TestServer_TelemetryDisable(t *testing.T) {
+	// Set the default telemetry to true (normally disabled in tests).
+	t.Setenv("CODER_TEST_TELEMETRY_DEFAULT_ENABLE", "true")
+
+	//nolint:paralleltest // No need to reinitialise the variable tt (Go version).
+	for _, tt := range []struct {
+		key  string
+		val  string
+		want bool
+	}{
+		{"", "", true},
+		{"CODER_TELEMETRY_ENABLE", "true", true},
+		{"CODER_TELEMETRY_ENABLE", "false", false},
+		{"CODER_TELEMETRY", "true", true},
+		{"CODER_TELEMETRY", "false", false},
+	} {
+		t.Run(fmt.Sprintf("%s=%s", tt.key, tt.val), func(t *testing.T) {
+			t.Parallel()
+			var b bytes.Buffer
+			inv, _ := clitest.New(t, "server", "--write-config")
+			inv.Stdout = &b
+			inv.Environ.Set(tt.key, tt.val)
+			clitest.Run(t, inv)
+
+			var dv codersdk.DeploymentValues
+			err := yaml.Unmarshal(b.Bytes(), &dv)
+			require.NoError(t, err)
+			assert.Equal(t, tt.want, dv.Telemetry.Enable.Value())
+		})
+	}
+}
+
 //nolint:tparallel,paralleltest // This test cannot be run in parallel due to signal handling.
 func TestServer_InterruptShutdown(t *testing.T) {
 	t.Skip("This test issues an interrupt signal which will propagate to the test runner.")
diff --git a/codersdk/deployment.go b/codersdk/deployment.go
index 5959c35fa9d95..0a97da7d3958f 100644
--- a/codersdk/deployment.go
+++ b/codersdk/deployment.go
@@ -1143,6 +1143,16 @@ when required by your organization's security policy.`,
 		Group:       &deploymentGroupEmailTLS,
 		YAML:        "certKeyFile",
 	}
+	telemetryEnable := serpent.Option{
+		Name:        "Telemetry Enable",
+		Description: "Whether telemetry is enabled or not. Coder collects anonymized usage data to help improve our product.",
+		Flag:        "telemetry",
+		Env:         "CODER_TELEMETRY_ENABLE",
+		Default:     strconv.FormatBool(flag.Lookup("test.v") == nil || os.Getenv("CODER_TEST_TELEMETRY_DEFAULT_ENABLE") == "true"),
+		Value:       &c.Telemetry.Enable,
+		Group:       &deploymentGroupTelemetry,
+		YAML:        "enable",
+	}
 	opts := serpent.OptionSet{
 		{
 			Name:        "Access URL",
@@ -1903,15 +1913,19 @@ when required by your organization's security policy.`,
 			YAML:  "dangerousSkipIssuerChecks",
 		},
 		// Telemetry settings
+		telemetryEnable,
 		{
-			Name:        "Telemetry Enable",
-			Description: "Whether telemetry is enabled or not. Coder collects anonymized usage data to help improve our product.",
-			Flag:        "telemetry",
-			Env:         "CODER_TELEMETRY_ENABLE",
-			Default:     strconv.FormatBool(flag.Lookup("test.v") == nil),
-			Value:       &c.Telemetry.Enable,
-			Group:       &deploymentGroupTelemetry,
-			YAML:        "enable",
+			Hidden: true,
+			Name:   "Telemetry (backwards compatibility)",
+			// Note the flip-flop of flag and env to maintain backwards
+			// compatibility and consistency. Inconsistently, the env
+			// was renamed to CODER_TELEMETRY_ENABLE in the past, but
+			// the flag was not renamed -enable.
+			Flag:       "telemetry-enable",
+			Env:        "CODER_TELEMETRY",
+			Value:      &c.Telemetry.Enable,
+			Group:      &deploymentGroupTelemetry,
+			UseInstead: []serpent.Option{telemetryEnable},
 		},
 		{
 			Name:        "Telemetry URL",
diff --git a/go.mod b/go.mod
index 49603fe69e8a3..3fd95bc456df2 100644
--- a/go.mod
+++ b/go.mod
@@ -204,7 +204,7 @@ require (
 	github.com/charmbracelet/bubbles v0.20.0
 	github.com/charmbracelet/bubbletea v1.1.0
 	github.com/charmbracelet/lipgloss v1.0.0
-	github.com/coder/serpent v0.8.0
+	github.com/coder/serpent v0.9.0
 	github.com/emersion/go-sasl v0.0.0-20200509203442-7bfe0ed36a21
 	github.com/emersion/go-smtp v0.21.2
 	github.com/go-jose/go-jose/v4 v4.0.2
diff --git a/go.sum b/go.sum
index 5f7ad74b2e704..c625d5d82b060 100644
--- a/go.sum
+++ b/go.sum
@@ -228,8 +228,8 @@ github.com/coder/quartz v0.1.2 h1:PVhc9sJimTdKd3VbygXtS4826EOCpB1fXoRlLnCrE+s=
 github.com/coder/quartz v0.1.2/go.mod h1:vsiCc+AHViMKH2CQpGIpFgdHIEQsxwm8yCscqKmzbRA=
 github.com/coder/retry v1.5.1 h1:iWu8YnD8YqHs3XwqrqsjoBTAVqT9ml6z9ViJ2wlMiqc=
 github.com/coder/retry v1.5.1/go.mod h1:blHMk9vs6LkoRT9ZHyuZo360cufXEhrxqvEzeMtRGoY=
-github.com/coder/serpent v0.8.0 h1:6OR+k6fekhSeEDmwwzBgnSjaa7FfGGrMlc3GoAEH9dg=
-github.com/coder/serpent v0.8.0/go.mod h1:cZFW6/fP+kE9nd/oRkEHJpG6sXCtQ+AX7WMMEHv0Y3Q=
+github.com/coder/serpent v0.9.0 h1:gfoTNOUitVdO1ZeZKk8xHiFjBvjzCQXxcMpZ7Dg41Qg=
+github.com/coder/serpent v0.9.0/go.mod h1:cZFW6/fP+kE9nd/oRkEHJpG6sXCtQ+AX7WMMEHv0Y3Q=
 github.com/coder/ssh v0.0.0-20231128192721-70855dedb788 h1:YoUSJ19E8AtuUFVYBpXuOD6a/zVP3rcxezNsoDseTUw=
 github.com/coder/ssh v0.0.0-20231128192721-70855dedb788/go.mod h1:aGQbuCLyhRLMzZF067xc84Lh7JDs1FKwCmF1Crl9dxQ=
 github.com/coder/tailscale v1.1.1-0.20241003034647-02286e537fc2 h1:mBbPFyJ2i9o490IwWGvWgtG0qmvIk45R7GWJpoaXotI=