diff --git a/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java b/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java
index 2370a3e5fb..84b84fdd42 100644
--- a/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java
+++ b/spring-boot-actuator/src/main/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfiguration.java
@@ -150,7 +150,7 @@ public class EndpointWebMvcAutoConfiguration
 			}
 		}
 		if (managementPort == ManagementServerPort.SAME) {
-			if (environment.getProperty("management.ssl.enabled") != null) {
+			if (environment.getProperty("management.ssl.enabled", Boolean.class, false)) {
 				throw new IllegalStateException(
 						"Management-specific SSL cannot be configured as the management "
 								+ "server is not listening on a separate port");
diff --git a/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java b/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java
index 42ab3033f5..6d095de08f 100755
--- a/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java
+++ b/spring-boot-actuator/src/test/java/org/springframework/boot/actuate/autoconfigure/EndpointWebMvcAutoConfigurationTests.java
@@ -561,6 +561,17 @@ public class EndpointWebMvcAutoConfigurationTests {
 		this.applicationContext.refresh();
 	}
 
+	@Test
+	public void samePortCanBeUsedWhenManagementSslIsExplicitlyDisabled()
+			throws Exception {
+		TestPropertyValues.of("management.ssl.enabled=false")
+				.applyTo(this.applicationContext);
+		this.applicationContext.register(RootConfig.class, EndpointConfig.class,
+				BaseConfiguration.class, EndpointWebMvcAutoConfiguration.class,
+				ErrorMvcAutoConfiguration.class);
+		this.applicationContext.refresh();
+	}
+
 	@Test
 	public void managementServerCanDisableSslWhenUsingADifferentPort() throws Exception {
 		TestPropertyValues.of("management.port=" + ports.get().management,