diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatReactiveWebServerFactory.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatReactiveWebServerFactory.java
index ff6d8e729cc2..4981bb81e9f1 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatReactiveWebServerFactory.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatReactiveWebServerFactory.java
@@ -200,8 +200,6 @@ protected void customizeConnector(Connector connector) {
 		if (getUriEncoding() != null) {
 			connector.setURIEncoding(getUriEncoding().name());
 		}
-		// Don't bind to the socket prematurely if ApplicationContext is slow to start
-		connector.setProperty("bindOnInit", "false");
 		if (getHttp2() != null && getHttp2().isEnabled()) {
 			connector.addUpgradeProtocol(new Http2Protocol());
 		}
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactory.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactory.java
index 5c60b0c7a909..5faed28060ab 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactory.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactory.java
@@ -342,8 +342,6 @@ protected void customizeConnector(Connector connector) {
 		if (getUriEncoding() != null) {
 			connector.setURIEncoding(getUriEncoding().name());
 		}
-		// Don't bind to the socket prematurely if ApplicationContext is slow to start
-		connector.setProperty("bindOnInit", "false");
 		if (getHttp2() != null && getHttp2().isEnabled()) {
 			connector.addUpgradeProtocol(new Http2Protocol());
 		}
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java
index 7d7ce965468e..6aa6a8cefbed 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/TomcatWebServer.java
@@ -20,6 +20,7 @@
 import java.util.HashMap;
 import java.util.Map;
 import java.util.concurrent.atomic.AtomicInteger;
+import java.util.function.BiConsumer;
 import java.util.stream.Collectors;
 
 import javax.naming.NamingException;
@@ -119,6 +120,8 @@ private void initialize() throws WebServerException {
 					}
 				});
 
+				disableBindOnInit();
+
 				// Start the server to trigger initialization listeners
 				this.tomcat.start();
 
@@ -162,12 +165,29 @@ private void addInstanceIdToEngineName() {
 	}
 
 	private void removeServiceConnectors() {
-		for (Service service : this.tomcat.getServer().findServices()) {
-			Connector[] connectors = service.findConnectors().clone();
+		doWithConnectors((service, connectors) -> {
 			this.serviceConnectors.put(service, connectors);
 			for (Connector connector : connectors) {
 				service.removeConnector(connector);
 			}
+		});
+	}
+
+	private void disableBindOnInit() {
+		doWithConnectors((service, connectors) -> {
+			for (Connector connector : connectors) {
+				Object bindOnInit = connector.getProperty("bindOnInit");
+				if (bindOnInit == null) {
+					connector.setProperty("bindOnInit", "false");
+				}
+			}
+		});
+	}
+
+	private void doWithConnectors(BiConsumer<Service, Connector[]> consumer) {
+		for (Service service : this.tomcat.getServer().findServices()) {
+			Connector[] connectors = service.findConnectors().clone();
+			consumer.accept(service, connectors);
 		}
 	}
 
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java
index 5dafd69bc45c..b9a9f58e5c7f 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/TomcatServletWebServerFactoryTests.java
@@ -237,11 +237,23 @@ void tomcatProtocolHandlerCanBeCustomized() {
 	void tomcatAdditionalConnectors() {
 		TomcatServletWebServerFactory factory = getFactory();
 		Connector[] connectors = new Connector[4];
-		Arrays.setAll(connectors, (i) -> new Connector());
+		Arrays.setAll(connectors, (i) -> {
+			Connector connector = new Connector();
+			connector.setPort(0);
+			return connector;
+		});
 		factory.addAdditionalTomcatConnectors(connectors);
 		this.webServer = factory.getWebServer();
-		Map<Service, Connector[]> connectorsByService = ((TomcatWebServer) this.webServer).getServiceConnectors();
+		Map<Service, Connector[]> connectorsByService = new HashMap<>(
+				((TomcatWebServer) this.webServer).getServiceConnectors());
 		assertThat(connectorsByService.values().iterator().next()).hasSize(connectors.length + 1);
+		this.webServer.start();
+		this.webServer.stop();
+		connectorsByService.forEach((service, serviceConnectors) -> {
+			for (Connector connector : serviceConnectors) {
+				assertThat(connector.getProtocolHandler()).extracting("endpoint.serverSock").isNull();
+			}
+		});
 	}
 
 	@Test