diff --git a/cli/deployment/config.go b/cli/deployment/config.go
index ab0c0645cea45..1b32a36d6efb8 100644
--- a/cli/deployment/config.go
+++ b/cli/deployment/config.go
@@ -239,6 +239,7 @@ func newConfig() *codersdk.DeploymentConfig {
 				Name:    "Telemetry Enable",
 				Usage:   "Whether telemetry is enabled or not. Coder collects anonymized usage data to help improve our product.",
 				Flag:    "telemetry",
+				Env:     "CODER_TELEMETRY", // Override default environment.
 				Default: flag.Lookup("test.v") == nil,
 			},
 			Trace: &codersdk.DeploymentConfigField[bool]{
@@ -294,6 +295,7 @@ func newConfig() *codersdk.DeploymentConfig {
 				Name:  "Trace Enable",
 				Usage: "Whether application tracing data is collected. It exports to a backend configured by environment variables. See: https://github.com/open-telemetry/opentelemetry-specification/blob/main/specification/protocol/exporter.md",
 				Flag:  "trace",
+				Env:   "CODER_TRACE", // Override default environment.
 			},
 			HoneycombAPIKey: &codersdk.DeploymentConfigField[string]{
 				Name:   "Trace Honeycomb API Key",
@@ -370,7 +372,6 @@ func Config(flagset *pflag.FlagSet, vip *viper.Viper) (*codersdk.DeploymentConfi
 		return nil, xerrors.Errorf("get global config from flag: %w", err)
 	}
 	vip.SetEnvPrefix("coder")
-	vip.AutomaticEnv()
 
 	if flg != "" {
 		vip.SetConfigFile(flg + "/server.yaml")
@@ -385,6 +386,18 @@ func Config(flagset *pflag.FlagSet, vip *viper.Viper) (*codersdk.DeploymentConfi
 	return dc, nil
 }
 
+func setEnv(prefix string, vip *viper.Viper, val reflect.Value) {
+	env := val.FieldByName("Env").String()
+	if env == "" {
+		env = formatEnv(prefix)
+	}
+	// Ensure the Env field is always populated.
+	val.FieldByName("Env").SetString(env)
+
+	// Ensure the auto-generated or manually named env is bound.
+	vip.MustBindEnv(prefix, env)
+}
+
 func setConfig(prefix string, vip *viper.Viper, target interface{}) {
 	val := reflect.Indirect(reflect.ValueOf(target))
 	typ := val.Type()
@@ -393,21 +406,26 @@ func setConfig(prefix string, vip *viper.Viper, target interface{}) {
 		typ = val.Type()
 	}
 
-	// Manually bind to env to support CODER_$INDEX_$FIELD format for structured slices.
-	_ = vip.BindEnv(prefix, formatEnv(prefix))
-
+	// Ensure that we only bind env variables to proper fields,
+	// otherwise Viper will get confused if the parent struct is
+	// assigned a value.
 	if strings.HasPrefix(typ.Name(), "DeploymentConfigField[") {
 		value := val.FieldByName("Value").Interface()
 		switch value.(type) {
 		case string:
+			setEnv(prefix, vip, val)
 			val.FieldByName("Value").SetString(vip.GetString(prefix))
 		case bool:
+			setEnv(prefix, vip, val)
 			val.FieldByName("Value").SetBool(vip.GetBool(prefix))
 		case int:
+			setEnv(prefix, vip, val)
 			val.FieldByName("Value").SetInt(int64(vip.GetInt(prefix)))
 		case time.Duration:
+			setEnv(prefix, vip, val)
 			val.FieldByName("Value").SetInt(int64(vip.GetDuration(prefix)))
 		case []string:
+			setEnv(prefix, vip, val)
 			// As of October 21st, 2022 we supported delimiting a string
 			// with a comma, but Viper only supports with a space. This
 			// is a small hack around it!
@@ -422,6 +440,7 @@ func setConfig(prefix string, vip *viper.Viper, target interface{}) {
 			}
 			val.FieldByName("Value").Set(reflect.ValueOf(value))
 		case []codersdk.GitAuthConfig:
+			// Do not bind to CODER_GITAUTH, instead bind to CODER_GITAUTH_0_*, etc.
 			values := readSliceFromViper[codersdk.GitAuthConfig](vip, prefix, value)
 			val.FieldByName("Value").Set(reflect.ValueOf(values))
 		default:
@@ -471,6 +490,11 @@ func readSliceFromViper[T any](vip *viper.Viper, key string, value any) []T {
 				prop = fve.Tag.Get("yaml")
 			}
 			configKey := fmt.Sprintf("%s.%d.%s", key, entry, prop)
+
+			// Ensure the env entry for this key is registered
+			// before checking value.
+			vip.MustBindEnv(configKey, formatEnv(configKey))
+
 			value := vip.Get(configKey)
 			if value == nil {
 				continue
@@ -502,7 +526,6 @@ func NewViper() *viper.Viper {
 	dc := newConfig()
 	vip := viper.New()
 	vip.SetEnvPrefix("coder")
-	vip.AutomaticEnv()
 	vip.SetEnvKeyReplacer(strings.NewReplacer("-", "_", ".", "_"))
 
 	setViperDefaults("", vip, dc)
@@ -560,12 +583,21 @@ func setFlags(prefix string, flagset *pflag.FlagSet, vip *viper.Viper, target in
 		if flg == "" {
 			return
 		}
+
+		env := val.FieldByName("Env").String()
+		if env == "" {
+			env = formatEnv(prefix)
+		}
 		usage := val.FieldByName("Usage").String()
-		usage = fmt.Sprintf("%s\n%s", usage, cliui.Styles.Placeholder.Render("Consumes $"+formatEnv(prefix)))
+		usage = fmt.Sprintf("%s\n%s", usage, cliui.Styles.Placeholder.Render("Consumes $"+env))
 		shorthand := val.FieldByName("Shorthand").String()
 		hidden := val.FieldByName("Hidden").Bool()
 		value := val.FieldByName("Default").Interface()
 
+		// Allow currently set environment variables
+		// to override default values in help output.
+		vip.MustBindEnv(prefix, env)
+
 		switch value.(type) {
 		case string:
 			_ = flagset.StringP(flg, shorthand, vip.GetString(prefix), usage)
diff --git a/cli/deployment/config_test.go b/cli/deployment/config_test.go
index d86c8e06a29b6..52cae36e17165 100644
--- a/cli/deployment/config_test.go
+++ b/cli/deployment/config_test.go
@@ -35,7 +35,7 @@ func TestConfig(t *testing.T) {
 			"CODER_PROVISIONER_DAEMONS":  "5",
 			"CODER_SECURE_AUTH_COOKIE":   "true",
 			"CODER_SSH_KEYGEN_ALGORITHM": "potato",
-			"CODER_TELEMETRY":            "false",
+			"CODER_TELEMETRY":            "true",
 			"CODER_TELEMETRY_TRACE":      "false",
 			"CODER_WILDCARD_ACCESS_URL":  "something-wildcard.com",
 		},
@@ -50,7 +50,7 @@ func TestConfig(t *testing.T) {
 			require.Equal(t, config.ProvisionerDaemons.Value, 5)
 			require.Equal(t, config.SecureAuthCookie.Value, true)
 			require.Equal(t, config.SSHKeygenAlgorithm.Value, "potato")
-			require.Equal(t, config.Telemetry.Enable.Value, false)
+			require.Equal(t, config.Telemetry.Enable.Value, true)
 			require.Equal(t, config.Telemetry.Trace.Value, false)
 			require.Equal(t, config.WildcardAccessURL.Value, "something-wildcard.com")
 		},
@@ -117,7 +117,7 @@ func TestConfig(t *testing.T) {
 	}, {
 		Name: "Trace",
 		Env: map[string]string{
-			"CODER_TRACE_ENABLE":            "true",
+			"CODER_TRACE":                   "true",
 			"CODER_TRACE_HONEYCOMB_API_KEY": "my-honeycomb-key",
 		},
 		Valid: func(config *codersdk.DeploymentConfig) {
@@ -199,6 +199,23 @@ func TestConfig(t *testing.T) {
 				Regex:        "gitlab.com",
 			}}, config.GitAuth.Value)
 		},
+	}, {
+		Name: "Wrong env must not break default values",
+		Env: map[string]string{
+			"CODER_PROMETHEUS_ENABLE": "true",
+			"CODER_PROMETHEUS":        "true", // Wrong env name, must not break prom addr.
+		},
+		Valid: func(config *codersdk.DeploymentConfig) {
+			require.Equal(t, config.Prometheus.Enable.Value, true)
+			require.Equal(t, config.Prometheus.Address.Value, config.Prometheus.Address.Default)
+		},
+	}, {
+		Name: "Env fields are populated with manual or automatic name",
+		Valid: func(config *codersdk.DeploymentConfig) {
+			require.Equal(t, config.Trace.Enable.Env, "CODER_TRACE")                    // Manual
+			require.Equal(t, config.Telemetry.Enable.Env, "CODER_TELEMETRY")            // Manual
+			require.Equal(t, config.Prometheus.Address.Env, "CODER_PROMETHEUS_ADDRESS") // Automatic
+		},
 	}} {
 		tc := tc
 		t.Run(tc.Name, func(t *testing.T) {
diff --git a/codersdk/deploymentconfig.go b/codersdk/deploymentconfig.go
index a73385670575a..248da8ee23bda 100644
--- a/codersdk/deploymentconfig.go
+++ b/codersdk/deploymentconfig.go
@@ -131,6 +131,7 @@ type DeploymentConfigField[T Flaggable] struct {
 	Name       string `json:"name"`
 	Usage      string `json:"usage"`
 	Flag       string `json:"flag"`
+	Env        string `json:"env"`
 	Shorthand  string `json:"shorthand"`
 	Enterprise bool   `json:"enterprise"`
 	Hidden     bool   `json:"hidden"`
@@ -146,6 +147,7 @@ func (f *DeploymentConfigField[T]) MarshalJSON() ([]byte, error) {
 		Name       string `json:"name"`
 		Usage      string `json:"usage"`
 		Flag       string `json:"flag"`
+		Env        string `json:"env"`
 		Shorthand  string `json:"shorthand"`
 		Enterprise bool   `json:"enterprise"`
 		Hidden     bool   `json:"hidden"`
@@ -156,6 +158,7 @@ func (f *DeploymentConfigField[T]) MarshalJSON() ([]byte, error) {
 		Name:       f.Name,
 		Usage:      f.Usage,
 		Flag:       f.Flag,
+		Env:        f.Env,
 		Shorthand:  f.Shorthand,
 		Enterprise: f.Enterprise,
 		Hidden:     f.Hidden,
diff --git a/site/src/api/typesGenerated.ts b/site/src/api/typesGenerated.ts
index 764aab5c6e761..9f613ba4cf5d6 100644
--- a/site/src/api/typesGenerated.ts
+++ b/site/src/api/typesGenerated.ts
@@ -310,6 +310,7 @@ export interface DeploymentConfigField<T extends Flaggable> {
   readonly name: string
   readonly usage: string
   readonly flag: string
+  readonly env: string
   readonly shorthand: string
   readonly enterprise: boolean
   readonly hidden: boolean