diff --git a/Dockerfile b/Dockerfile
index 9d34317a..50fdde90 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -113,6 +113,7 @@ ENV VPNSP=pia \
     # Health
     HEALTH_OPENVPN_DURATION_INITIAL=6s \
     HEALTH_OPENVPN_DURATION_ADDITION=5s \
+    HEALTH_SERVER_ADDRESS=127.0.0.1:9999 \
     # DNS over TLS
     DOT=on \
     DOT_PROVIDERS=cloudflare \
diff --git a/cmd/gluetun/main.go b/cmd/gluetun/main.go
index 4e808d47..6e3c4119 100644
--- a/cmd/gluetun/main.go
+++ b/cmd/gluetun/main.go
@@ -71,10 +71,11 @@ func main() {
 	osUser := user.New()
 	unix := unix.New()
 	cli := cli.New()
+	env := params.NewEnv()
 
 	errorCh := make(chan error)
 	go func() {
-		errorCh <- _main(ctx, buildInfo, args, logger, os, osUser, unix, cli)
+		errorCh <- _main(ctx, buildInfo, args, logger, env, os, osUser, unix, cli)
 	}()
 
 	select {
@@ -112,12 +113,12 @@ var (
 
 //nolint:gocognit,gocyclo
 func _main(ctx context.Context, buildInfo models.BuildInformation,
-	args []string, logger logging.ParentLogger, os os.OS,
+	args []string, logger logging.ParentLogger, env params.Env, os os.OS,
 	osUser user.OSUser, unix unix.Unix, cli cli.CLI) error {
 	if len(args) > 1 { // cli operation
 		switch args[1] {
 		case "healthcheck":
-			return cli.HealthCheck(ctx)
+			return cli.HealthCheck(ctx, env, os, logger)
 		case "clientkey":
 			return cli.ClientKey(args[2:], os.OpenFile)
 		case "openvpnconfig":
@@ -159,7 +160,7 @@ func _main(ctx context.Context, buildInfo models.BuildInformation,
 	}
 
 	var allSettings configuration.Settings
-	err := allSettings.Read(params.NewEnv(), os,
+	err := allSettings.Read(env, os,
 		logger.NewChild(logging.Settings{Prefix: "configuration: "}))
 	if err != nil {
 		return err
@@ -365,8 +366,7 @@ func _main(ctx context.Context, buildInfo models.BuildInformation,
 	controlGroupHandler.Add(httpServerHandler)
 
 	healthLogger := logger.NewChild(logging.Settings{Prefix: "healthcheck: "})
-	healthcheckServer := healthcheck.NewServer(constants.HealthcheckAddress,
-		allSettings.Health, healthLogger, openvpnLooper)
+	healthcheckServer := healthcheck.NewServer(allSettings.Health, healthLogger, openvpnLooper)
 	healthServerHandler, healthServerCtx, healthServerDone := goshutdown.NewGoRoutineHandler(
 		"HTTP health server", defaultGoRoutineSettings)
 	go healthcheckServer.Run(healthServerCtx, healthServerDone)
diff --git a/internal/cli/cli.go b/internal/cli/cli.go
index d5828cef..1664f459 100644
--- a/internal/cli/cli.go
+++ b/internal/cli/cli.go
@@ -6,11 +6,12 @@ import (
 
 	"github.com/qdm12/golibs/logging"
 	"github.com/qdm12/golibs/os"
+	"github.com/qdm12/golibs/params"
 )
 
 type CLI interface {
 	ClientKey(args []string, openFile os.OpenFileFunc) error
-	HealthCheck(ctx context.Context) error
+	HealthCheck(ctx context.Context, env params.Env, os os.OS, logger logging.Logger) error
 	OpenvpnConfig(os os.OS, logger logging.Logger) error
 	Update(ctx context.Context, args []string, os os.OS, logger logging.Logger) error
 }
diff --git a/internal/cli/healthcheck.go b/internal/cli/healthcheck.go
index 3513d5af..95543c9b 100644
--- a/internal/cli/healthcheck.go
+++ b/internal/cli/healthcheck.go
@@ -2,19 +2,36 @@ package cli
 
 import (
 	"context"
+	"net"
 	"net/http"
 	"time"
 
-	"github.com/qdm12/gluetun/internal/constants"
+	"github.com/qdm12/gluetun/internal/configuration"
 	"github.com/qdm12/gluetun/internal/healthcheck"
+	"github.com/qdm12/golibs/logging"
+	"github.com/qdm12/golibs/os"
+	"github.com/qdm12/golibs/params"
 )
 
-func (c *cli) HealthCheck(ctx context.Context) error {
+func (c *cli) HealthCheck(ctx context.Context, env params.Env,
+	os os.OS, logger logging.Logger) error {
+	// Extract the health server port from the configuration.
+	config := configuration.Health{}
+	err := config.Read(env, os, logger)
+	if err != nil {
+		return err
+	}
+	_, port, err := net.SplitHostPort(config.ServerAddress)
+	if err != nil {
+		return err
+	}
+
 	const timeout = 10 * time.Second
 	httpClient := &http.Client{Timeout: timeout}
 	healthchecker := healthcheck.NewChecker(httpClient)
 	ctx, cancel := context.WithTimeout(ctx, timeout)
 	defer cancel()
-	const url = "http://" + constants.HealthcheckAddress
+
+	url := "http://127.0.0.1:" + port
 	return healthchecker.Check(ctx, url)
 }
diff --git a/internal/configuration/health.go b/internal/configuration/health.go
index 409d6610..2af20114 100644
--- a/internal/configuration/health.go
+++ b/internal/configuration/health.go
@@ -3,12 +3,15 @@ package configuration
 import (
 	"strings"
 
+	"github.com/qdm12/golibs/logging"
+	"github.com/qdm12/golibs/os"
 	"github.com/qdm12/golibs/params"
 )
 
 // Health contains settings for the healthcheck and health server.
 type Health struct {
-	OpenVPN HealthyWait
+	ServerAddress string
+	OpenVPN       HealthyWait
 }
 
 func (settings *Health) String() string {
@@ -18,6 +21,8 @@ func (settings *Health) String() string {
 func (settings *Health) lines() (lines []string) {
 	lines = append(lines, lastIndent+"Health:")
 
+	lines = append(lines, indent+lastIndent+"Server address: "+settings.ServerAddress)
+
 	lines = append(lines, indent+lastIndent+"OpenVPN:")
 	for _, line := range settings.OpenVPN.lines() {
 		lines = append(lines, indent+indent+line)
@@ -26,7 +31,23 @@ func (settings *Health) lines() (lines []string) {
 	return lines
 }
 
+// Read is to be used for the healthcheck query mode.
+func (settings *Health) Read(env params.Env, os os.OS, logger logging.Logger) (err error) {
+	reader := newReader(env, os, logger)
+	return settings.read(reader)
+}
+
 func (settings *Health) read(r reader) (err error) {
+	var warning string
+	settings.ServerAddress, warning, err = r.env.ListeningAddress(
+		"HEALTH_SERVER_ADDRESS", params.Default("127.0.0.1:9999"))
+	if warning != "" {
+		r.logger.Warn("health server address: " + warning)
+	}
+	if err != nil {
+		return err
+	}
+
 	settings.OpenVPN.Initial, err = r.env.Duration("HEALTH_OPENVPN_DURATION_INITIAL", params.Default("6s"))
 	if err != nil {
 		return err
diff --git a/internal/configuration/health_test.go b/internal/configuration/health_test.go
index aa99994d..9a1add46 100644
--- a/internal/configuration/health_test.go
+++ b/internal/configuration/health_test.go
@@ -6,6 +6,7 @@ import (
 	"time"
 
 	"github.com/golang/mock/gomock"
+	"github.com/qdm12/golibs/logging/mock_logging"
 	"github.com/qdm12/golibs/params/mock_params"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -15,7 +16,7 @@ func Test_Health_String(t *testing.T) {
 	t.Parallel()
 
 	var health Health
-	const expected = "|--Health:\n   |--OpenVPN:\n      |--Initial duration: 0s"
+	const expected = "|--Health:\n   |--Server address: \n   |--OpenVPN:\n      |--Initial duration: 0s"
 
 	s := health.String()
 
@@ -32,12 +33,14 @@ func Test_Health_lines(t *testing.T) {
 		"empty": {
 			lines: []string{
 				"|--Health:",
+				"   |--Server address: ",
 				"   |--OpenVPN:",
 				"      |--Initial duration: 0s",
 			},
 		},
 		"filled settings": {
 			settings: Health{
+				ServerAddress: "address:9999",
 				OpenVPN: HealthyWait{
 					Initial:  time.Second,
 					Addition: time.Minute,
@@ -45,6 +48,7 @@ func Test_Health_lines(t *testing.T) {
 			},
 			lines: []string{
 				"|--Health:",
+				"   |--Server address: address:9999",
 				"   |--OpenVPN:",
 				"      |--Initial duration: 1s",
 				"      |--Addition duration: 1m0s",
@@ -74,19 +78,35 @@ func Test_Health_read(t *testing.T) {
 		openvpnInitialErr       error
 		openvpnAdditionDuration time.Duration
 		openvpnAdditionErr      error
+		serverAddress           string
+		serverAddressWarning    string
+		serverAddressErr        error
 		expected                Health
 		err                     error
 	}{
 		"success": {
 			openvpnInitialDuration:  time.Second,
 			openvpnAdditionDuration: time.Minute,
+			serverAddress:           "127.0.0.1:9999",
 			expected: Health{
+				ServerAddress: "127.0.0.1:9999",
 				OpenVPN: HealthyWait{
 					Initial:  time.Second,
 					Addition: time.Minute,
 				},
 			},
 		},
+		"listening address error": {
+			openvpnInitialDuration:  time.Second,
+			openvpnAdditionDuration: time.Minute,
+			serverAddress:           "127.0.0.1:9999",
+			serverAddressWarning:    "warning",
+			serverAddressErr:        errDummy,
+			expected: Health{
+				ServerAddress: "127.0.0.1:9999",
+			},
+			err: errDummy,
+		},
 		"initial error": {
 			openvpnInitialDuration:  time.Second,
 			openvpnInitialErr:       errDummy,
@@ -120,17 +140,29 @@ func Test_Health_read(t *testing.T) {
 			ctrl := gomock.NewController(t)
 
 			env := mock_params.NewMockEnv(ctrl)
-			env.EXPECT().
-				Duration("HEALTH_OPENVPN_DURATION_INITIAL", gomock.Any()).
-				Return(testCase.openvpnInitialDuration, testCase.openvpnInitialErr)
-			if testCase.openvpnInitialErr == nil {
+			logger := mock_logging.NewMockLogger(ctrl)
+
+			env.EXPECT().ListeningAddress("HEALTH_SERVER_ADDRESS", gomock.Any()).
+				Return(testCase.serverAddress, testCase.serverAddressWarning,
+					testCase.serverAddressErr)
+			if testCase.serverAddressWarning != "" {
+				logger.EXPECT().Warn("health server address: " + testCase.serverAddressWarning)
+			}
+
+			if testCase.serverAddressErr == nil {
 				env.EXPECT().
-					Duration("HEALTH_OPENVPN_DURATION_ADDITION", gomock.Any()).
-					Return(testCase.openvpnAdditionDuration, testCase.openvpnAdditionErr)
+					Duration("HEALTH_OPENVPN_DURATION_INITIAL", gomock.Any()).
+					Return(testCase.openvpnInitialDuration, testCase.openvpnInitialErr)
+				if testCase.openvpnInitialErr == nil {
+					env.EXPECT().
+						Duration("HEALTH_OPENVPN_DURATION_ADDITION", gomock.Any()).
+						Return(testCase.openvpnAdditionDuration, testCase.openvpnAdditionErr)
+				}
 			}
 
 			r := reader{
-				env: env,
+				env:    env,
+				logger: logger,
 			}
 
 			var health Health
diff --git a/internal/configuration/settings_test.go b/internal/configuration/settings_test.go
index c51b1c78..08d09b3c 100644
--- a/internal/configuration/settings_test.go
+++ b/internal/configuration/settings_test.go
@@ -38,6 +38,7 @@ func Test_Settings_lines(t *testing.T) {
 				"   |--Process group ID: 0",
 				"   |--Timezone: NOT SET ⚠️ - it can cause time related issues",
 				"|--Health:",
+				"   |--Server address: ",
 				"   |--OpenVPN:",
 				"      |--Initial duration: 0s",
 				"|--HTTP control server:",
diff --git a/internal/constants/addresses.go b/internal/constants/addresses.go
deleted file mode 100644
index 28c1f716..00000000
--- a/internal/constants/addresses.go
+++ /dev/null
@@ -1,6 +0,0 @@
-package constants
-
-const (
-	// HealthcheckAddress is the default listening address for the healthcheck server.
-	HealthcheckAddress = "127.0.0.1:9999"
-)
diff --git a/internal/healthcheck/server.go b/internal/healthcheck/server.go
index bcce922e..5788a958 100644
--- a/internal/healthcheck/server.go
+++ b/internal/healthcheck/server.go
@@ -17,7 +17,6 @@ type Server interface {
 }
 
 type server struct {
-	address  string
 	logger   logging.Logger
 	handler  *handler
 	resolver *net.Resolver
@@ -31,10 +30,9 @@ type openvpnHealth struct {
 	healthyTimer *time.Timer
 }
 
-func NewServer(address string, config configuration.Health,
+func NewServer(config configuration.Health,
 	logger logging.Logger, openvpnLooper openvpn.Looper) Server {
 	return &server{
-		address:  address,
 		logger:   logger,
 		handler:  newHandler(logger),
 		resolver: net.DefaultResolver,
@@ -53,7 +51,7 @@ func (s *server) Run(ctx context.Context, done chan<- struct{}) {
 	go s.runHealthcheckLoop(ctx, loopDone)
 
 	server := http.Server{
-		Addr:    s.address,
+		Addr:    s.config.ServerAddress,
 		Handler: s.handler,
 	}
 	serverDone := make(chan struct{})
@@ -68,7 +66,7 @@ func (s *server) Run(ctx context.Context, done chan<- struct{}) {
 		}
 	}()
 
-	s.logger.Info("listening on %s", s.address)
+	s.logger.Info("listening on " + s.config.ServerAddress)
 	err := server.ListenAndServe()
 	if err != nil && !errors.Is(ctx.Err(), context.Canceled) {
 		s.logger.Error(err)