diff --git a/caddy/caddy_test.go b/caddy/caddy_test.go
index a55654d4a2..09bd59eeb6 100644
--- a/caddy/caddy_test.go
+++ b/caddy/caddy_test.go
@@ -20,24 +20,25 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
-// waitForServerReady polls the server with retries until it responds to HTTP requests.
-// This handles a race condition during Caddy config reload on macOS where SO_REUSEPORT
-// can briefly route connections to the old listener being shut down,
+// initServer initializes a Caddy test server and waits for it to be ready.
+// After InitServer, it polls the server to handle a race condition on macOS where
+// SO_REUSEPORT can briefly route connections to the old listener being shut down,
 // resulting in "connection reset by peer".
-func waitForServerReady(t *testing.T, url string) {
+func initServer(t *testing.T, tester *caddytest.Tester, config string, format string) {
 	t.Helper()
+	tester.InitServer(config, format)
 
 	client := &http.Client{Timeout: 1 * time.Second}
-	for range 10 {
-		resp, err := client.Get(url)
-		if err == nil {
-			require.NoError(t, resp.Body.Close())
-
-			return
+	require.Eventually(t, func() bool {
+		resp, err := client.Get("http://localhost:" + testPort)
+		if err != nil {
+			return false
 		}
 
-		time.Sleep(100 * time.Millisecond)
-	}
+		require.NoError(t, resp.Body.Close())
+
+		return true
+	}, 5*time.Second, 100*time.Millisecond, "server failed to become ready")
 }
 
 var testPort = "9080"
@@ -74,7 +75,7 @@ func TestMain(m *testing.M) {
 func TestPHP(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -104,7 +105,7 @@ func TestPHP(t *testing.T) {
 
 func TestLargeRequest(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -133,7 +134,7 @@ func TestLargeRequest(t *testing.T) {
 func TestWorker(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -170,7 +171,7 @@ func TestGlobalAndModuleWorker(t *testing.T) {
 	testPortNum, _ := strconv.Atoi(testPort)
 	testPortTwo := strconv.Itoa(testPortNum + 1)
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -220,7 +221,7 @@ func TestGlobalAndModuleWorker(t *testing.T) {
 
 func TestModuleWorkerInheritsEnv(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -245,7 +246,7 @@ func TestNamedModuleWorkers(t *testing.T) {
 	testPortNum, _ := strconv.Atoi(testPort)
 	testPortTwo := strconv.Itoa(testPortNum + 1)
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -294,7 +295,7 @@ func TestNamedModuleWorkers(t *testing.T) {
 
 func TestEnv(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -325,7 +326,7 @@ func TestEnv(t *testing.T) {
 
 func TestJsonEnv(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 		"admin": {
 			"listen": "localhost:2999"
@@ -408,7 +409,7 @@ func TestJsonEnv(t *testing.T) {
 
 func TestCustomCaddyVariablesInEnv(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -442,7 +443,7 @@ func TestCustomCaddyVariablesInEnv(t *testing.T) {
 
 func TestPHPServerDirective(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -456,7 +457,6 @@ func TestPHPServerDirective(t *testing.T) {
 		}
 		`, "caddyfile")
 
-	waitForServerReady(t, "http://localhost:"+testPort)
 	tester.AssertGetResponse("http://localhost:"+testPort, http.StatusOK, "I am by birth a Genevese (i not set)")
 	tester.AssertGetResponse("http://localhost:"+testPort+"/hello.txt", http.StatusOK, "Hello\n")
 	tester.AssertGetResponse("http://localhost:"+testPort+"/not-found.txt", http.StatusOK, "I am by birth a Genevese (i not set)")
@@ -464,7 +464,7 @@ func TestPHPServerDirective(t *testing.T) {
 
 func TestPHPServerDirectiveDisableFileServer(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -482,7 +482,6 @@ func TestPHPServerDirectiveDisableFileServer(t *testing.T) {
 		}
 		`, "caddyfile")
 
-	waitForServerReady(t, "http://localhost:"+testPort)
 	tester.AssertGetResponse("http://localhost:"+testPort, http.StatusOK, "I am by birth a Genevese (i not set)")
 	tester.AssertGetResponse("http://localhost:"+testPort+"/not-found.txt", http.StatusOK, "I am by birth a Genevese (i not set)")
 }
@@ -490,7 +489,7 @@ func TestPHPServerDirectiveDisableFileServer(t *testing.T) {
 func TestMetrics(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -571,7 +570,7 @@ func TestMetrics(t *testing.T) {
 func TestWorkerMetrics(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -672,7 +671,7 @@ func TestWorkerMetrics(t *testing.T) {
 func TestNamedWorkerMetrics(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -767,7 +766,7 @@ func TestNamedWorkerMetrics(t *testing.T) {
 func TestAutoWorkerConfig(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -868,7 +867,7 @@ func TestAllDefinedServerVars(t *testing.T) {
 	expectedBody = strings.ReplaceAll(expectedBody, "{testPort}", testPort)
 	expectedBody = strings.ReplaceAll(expectedBody, documentRoot+"/", documentRoot+string(filepath.Separator))
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -900,7 +899,7 @@ func TestAllDefinedServerVars(t *testing.T) {
 
 func TestPHPIniConfiguration(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -928,7 +927,7 @@ func TestPHPIniConfiguration(t *testing.T) {
 
 func TestPHPIniBlockConfiguration(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -968,7 +967,7 @@ func testSingleIniConfiguration(tester *caddytest.Tester, key string, value stri
 
 func TestOsEnv(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -998,7 +997,7 @@ func TestOsEnv(t *testing.T) {
 
 func TestMaxWaitTime(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1039,7 +1038,7 @@ func TestMaxWaitTime(t *testing.T) {
 
 func TestMaxWaitTimeWorker(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1122,7 +1121,7 @@ func getStatusCode(url string, t *testing.T) int {
 func TestMultiWorkersMetrics(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -1231,7 +1230,7 @@ func TestMultiWorkersMetrics(t *testing.T) {
 func TestDisabledMetrics(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -1311,7 +1310,7 @@ func TestDisabledMetrics(t *testing.T) {
 func TestWorkerRestart(t *testing.T) {
 	var wg sync.WaitGroup
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 	{
 		skip_install_trust
 		admin localhost:2999
@@ -1413,7 +1412,7 @@ func TestWorkerRestart(t *testing.T) {
 
 func TestWorkerMatchDirective(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1446,7 +1445,7 @@ func TestWorkerMatchDirective(t *testing.T) {
 
 func TestWorkerMatchDirectiveWithMultipleWorkers(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1487,7 +1486,7 @@ func TestWorkerMatchDirectiveWithMultipleWorkers(t *testing.T) {
 
 func TestWorkerMatchDirectiveWithoutFileServer(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1520,7 +1519,7 @@ func TestWorkerMatchDirectiveWithoutFileServer(t *testing.T) {
 
 func TestDd(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1544,7 +1543,7 @@ func TestDd(t *testing.T) {
 
 func TestLog(t *testing.T) {
 	tester := caddytest.NewTester(t)
-	tester.InitServer(`
+	initServer(t, tester, `
 		{
 			skip_install_trust
 			admin localhost:2999
@@ -1582,7 +1581,7 @@ func TestSymlinkWorkerPaths(t *testing.T) {
 		// When I execute `frankenphp php-server --listen localhost:8080 -w index.php` from `public`
 		// Then I expect to see the worker script executed successfully
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1612,7 +1611,7 @@ func TestSymlinkWorkerPaths(t *testing.T) {
 		// When I execute `frankenphp --listen localhost:8080 -w nested/index.php` from `public`
 		// Then I expect to see the worker script executed successfully
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1642,7 +1641,7 @@ func TestSymlinkWorkerPaths(t *testing.T) {
 		// When I execute `frankenphp --listen localhost:8080 -w public/index.php` from the root folder
 		// Then I expect to see the worker script executed successfully
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1676,7 +1675,7 @@ func TestSymlinkWorkerPaths(t *testing.T) {
 		// When I execute `frankenphp --listen localhost:8080 -w public/index.php -r public` from the root folder
 		// Then I expect to see the worker script executed successfully
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1715,7 +1714,7 @@ func TestSymlinkResolveRoot(t *testing.T) {
 	t.Run("ResolveRootSymlink", func(t *testing.T) {
 		// Tests that resolve_root_symlink directive works correctly
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1743,7 +1742,7 @@ func TestSymlinkResolveRoot(t *testing.T) {
 	t.Run("NoResolveRootSymlink", func(t *testing.T) {
 		// Tests that symlinks are preserved when resolve_root_symlink is false (non-worker mode)
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1774,7 +1773,7 @@ func TestSymlinkWorkerBehavior(t *testing.T) {
 	t.Run("WorkerScriptFailsWithoutWorkerMode", func(t *testing.T) {
 		// Tests that accessing a worker-only script without configuring it as a worker actually results in an error
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999
@@ -1798,7 +1797,7 @@ func TestSymlinkWorkerBehavior(t *testing.T) {
 	t.Run("MultipleRequests", func(t *testing.T) {
 		// Tests that symlinked workers handle multiple requests correctly
 		tester := caddytest.NewTester(t)
-		tester.InitServer(`
+		initServer(t, tester, `
 			{
 				skip_install_trust
 				admin localhost:2999