diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfiguration.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfiguration.java
index 1db35b2379..f2384bd390 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfiguration.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfiguration.java
@@ -25,12 +25,14 @@ import org.springframework.boot.autoconfigure.AutoConfigureBefore;
 import org.springframework.boot.autoconfigure.EnableAutoConfiguration;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnWebApplication;
 import org.springframework.boot.autoconfigure.security.ConditionalOnDefaultWebSecurity;
+import org.springframework.boot.autoconfigure.security.SecurityProperties;
 import org.springframework.boot.autoconfigure.security.oauth2.client.servlet.OAuth2ClientAutoConfiguration;
 import org.springframework.boot.autoconfigure.security.oauth2.resource.servlet.OAuth2ResourceServerAutoConfiguration;
 import org.springframework.boot.autoconfigure.security.saml2.Saml2RelyingPartyAutoConfiguration;
 import org.springframework.boot.autoconfigure.security.servlet.SecurityAutoConfiguration;
 import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
+import org.springframework.core.annotation.Order;
 import org.springframework.security.config.Customizer;
 import org.springframework.security.config.annotation.web.builders.HttpSecurity;
 import org.springframework.security.web.SecurityFilterChain;
@@ -43,6 +45,7 @@ import org.springframework.security.web.SecurityFilterChain;
  * of the custom security configuration.
  *
  * @author Madhura Bhave
+ * @author Hatef Palizgar
  * @since 2.1.0
  */
 @Configuration(proxyBeanMethods = false)
@@ -55,6 +58,7 @@ import org.springframework.security.web.SecurityFilterChain;
 public class ManagementWebSecurityAutoConfiguration {
 
 	@Bean
+	@Order(SecurityProperties.BASIC_AUTH_ORDER)
 	SecurityFilterChain managementSecurityFilterChain(HttpSecurity http) throws Exception {
 		http.authorizeRequests((requests) -> {
 			requests.requestMatchers(EndpointRequest.to(HealthEndpoint.class)).permitAll();
diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfigurationTests.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfigurationTests.java
index 6dc70733ea..344aff2c3c 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfigurationTests.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/security/servlet/ManagementWebSecurityAutoConfigurationTests.java
@@ -17,6 +17,8 @@
 package org.springframework.boot.actuate.autoconfigure.security.servlet;
 
 import java.io.IOException;
+import java.util.List;
+import java.util.stream.Collectors;
 
 import org.junit.jupiter.api.Test;
 
@@ -27,6 +29,7 @@ import org.springframework.boot.actuate.autoconfigure.health.HealthContributorAu
 import org.springframework.boot.actuate.autoconfigure.health.HealthEndpointAutoConfiguration;
 import org.springframework.boot.actuate.autoconfigure.info.InfoEndpointAutoConfiguration;
 import org.springframework.boot.autoconfigure.AutoConfigurations;
+import org.springframework.boot.autoconfigure.security.SecurityProperties;
 import org.springframework.boot.autoconfigure.security.oauth2.resource.servlet.OAuth2ResourceServerAutoConfiguration;
 import org.springframework.boot.autoconfigure.security.saml2.Saml2RelyingPartyAutoConfiguration;
 import org.springframework.boot.autoconfigure.security.servlet.SecurityAutoConfiguration;
@@ -35,6 +38,7 @@ import org.springframework.boot.test.context.assertj.AssertableWebApplicationCon
 import org.springframework.boot.test.context.runner.WebApplicationContextRunner;
 import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
+import org.springframework.core.annotation.Order;
 import org.springframework.http.HttpStatus;
 import org.springframework.mock.web.MockFilterChain;
 import org.springframework.mock.web.MockHttpServletRequest;
@@ -45,6 +49,7 @@ import org.springframework.security.config.annotation.web.builders.HttpSecurity;
 import org.springframework.security.config.annotation.web.configuration.WebSecurityConfigurerAdapter;
 import org.springframework.security.web.FilterChainProxy;
 import org.springframework.security.web.SecurityFilterChain;
+import org.springframework.security.web.util.matcher.AntPathRequestMatcher;
 import org.springframework.web.context.WebApplicationContext;
 
 import static org.assertj.core.api.Assertions.assertThat;
@@ -53,6 +58,7 @@ import static org.assertj.core.api.Assertions.assertThat;
  * Tests for {@link ManagementWebSecurityAutoConfiguration}.
  *
  * @author Madhura Bhave
+ * @author Hatef Palizgar
  */
 class ManagementWebSecurityAutoConfigurationTests {
 
@@ -113,7 +119,7 @@ class ManagementWebSecurityAutoConfigurationTests {
 	@Test
 	void backsOffIfSecurityFilterChainBeanIsPresent() {
 		this.contextRunner.withUserConfiguration(TestSecurityFilterChainConfig.class).run((context) -> {
-			assertThat(context.getBeansOfType(SecurityFilterChain.class).size()).isEqualTo(1);
+			assertThat(context.getBeansOfType(SecurityFilterChain.class)).hasSize(1);
 			assertThat(context.containsBean("testSecurityFilterChain")).isTrue();
 		});
 	}
@@ -138,6 +144,21 @@ class ManagementWebSecurityAutoConfigurationTests {
 						.doesNotHaveBean(MANAGEMENT_SECURITY_FILTER_CHAIN_BEAN));
 	}
 
+	@Test
+	void backOffIfRemoteDevToolsSecurityFilterChainIsPresent() {
+		this.contextRunner.withUserConfiguration(TestRemoteDevToolsSecurityFilterChainConfig.class).run((context) -> {
+			SecurityFilterChain testSecurityFilterChain = context.getBean("testSecurityFilterChain",
+					SecurityFilterChain.class);
+			SecurityFilterChain testRemoteDevToolsSecurityFilterChain = context
+					.getBean("testRemoteDevToolsSecurityFilterChain", SecurityFilterChain.class);
+			List<SecurityFilterChain> orderedSecurityFilterChains = context.getBeanProvider(SecurityFilterChain.class)
+					.orderedStream().collect(Collectors.toList());
+			assertThat(orderedSecurityFilterChains).containsExactly(testRemoteDevToolsSecurityFilterChain,
+					testSecurityFilterChain);
+			assertThat(context).doesNotHaveBean(ManagementWebSecurityAutoConfiguration.class);
+		});
+	}
+
 	private HttpStatus getResponseStatus(AssertableWebApplicationContext context, String path)
 			throws IOException, javax.servlet.ServletException {
 		FilterChainProxy filterChainProxy = context.getBean(FilterChainProxy.class);
@@ -177,4 +198,16 @@ class ManagementWebSecurityAutoConfigurationTests {
 
 	}
 
+	@Configuration(proxyBeanMethods = false)
+	static class TestRemoteDevToolsSecurityFilterChainConfig extends TestSecurityFilterChainConfig {
+
+		@Bean
+		@Order(SecurityProperties.BASIC_AUTH_ORDER - 1)
+		SecurityFilterChain testRemoteDevToolsSecurityFilterChain(HttpSecurity http) throws Exception {
+			return http.requestMatcher(new AntPathRequestMatcher("/**")).authorizeRequests().anyRequest().anonymous()
+					.and().csrf().disable().build();
+		}
+
+	}
+
 }