diff --git a/spring-cloud-sleuth-core/src/main/java/org/springframework/cloud/sleuth/instrument/web/TraceWebAutoConfiguration.java b/spring-cloud-sleuth-core/src/main/java/org/springframework/cloud/sleuth/instrument/web/TraceWebAutoConfiguration.java
index bc43135d8..dbc2e963b 100644
--- a/spring-cloud-sleuth-core/src/main/java/org/springframework/cloud/sleuth/instrument/web/TraceWebAutoConfiguration.java
+++ b/spring-cloud-sleuth-core/src/main/java/org/springframework/cloud/sleuth/instrument/web/TraceWebAutoConfiguration.java
@@ -27,6 +27,8 @@ import brave.Tracing;
 
 import org.springframework.beans.factory.annotation.Autowired;
 import org.springframework.boot.actuate.autoconfigure.endpoint.web.WebEndpointProperties;
+import org.springframework.boot.actuate.autoconfigure.web.server.ConditionalOnManagementPort;
+import org.springframework.boot.actuate.autoconfigure.web.server.ManagementPortType;
 import org.springframework.boot.actuate.autoconfigure.web.server.ManagementServerProperties;
 import org.springframework.boot.actuate.endpoint.EndpointsSupplier;
 import org.springframework.boot.actuate.endpoint.web.ExposableWebEndpoint;
@@ -101,13 +103,12 @@ public class TraceWebAutoConfiguration {
 	}
 
 	@Configuration
-	@ConditionalOnClass({ ServerProperties.class, EndpointsSupplier.class,
-			ExposableWebEndpoint.class })
+	@ConditionalOnClass({ ServerProperties.class, EndpointsSupplier.class, ExposableWebEndpoint.class })
 	@ConditionalOnBean(ServerProperties.class)
 	@ConditionalOnProperty(value = "spring.sleuth.web.ignoreAutoConfiguredSkipPatterns", havingValue = "false", matchIfMissing = true)
 	protected static class ActuatorSkipPatternProviderConfig {
 
-		static Optional<Pattern> getEndpointsPatterns(ServerProperties serverProperties,
+		static Optional<Pattern> getEndpointsPatterns(String contextPath,
 				WebEndpointProperties webEndpointProperties,
 				EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier) {
 			Collection<ExposableWebEndpoint> endpoints = endpointsSupplier.getEndpoints();
@@ -116,8 +117,6 @@ public class TraceWebAutoConfiguration {
 				return Optional.empty();
 			}
 
-			String contextPath = serverProperties.getServlet().getContextPath();
-
 			String pattern = endpoints.stream().map(PathMappedEndpoint::getRootPath)
 					.map(path -> path + "|" + path + "/.*").collect(
 							Collectors.joining("|",
@@ -142,14 +141,24 @@ public class TraceWebAutoConfiguration {
 		}
 
 		@Bean
-		public SingleSkipPattern skipPatternForActuatorEndpoints(
+		@ConditionalOnManagementPort(ManagementPortType.SAME)
+		public SingleSkipPattern skipPatternForActuatorEndpointsSamePort(
 				final ServerProperties serverProperties,
 				final WebEndpointProperties webEndpointProperties,
 				final EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier) {
-			return () -> getEndpointsPatterns(serverProperties, webEndpointProperties,
-					endpointsSupplier);
+			return () -> getEndpointsPatterns(serverProperties.getServlet().getContextPath(), 
+				webEndpointProperties, endpointsSupplier);
+		}
+		
+		@Bean
+		@ConditionalOnManagementPort(ManagementPortType.DIFFERENT)
+		@ConditionalOnProperty(name = "management.server.servlet.context-path", havingValue = "/", matchIfMissing = true)
+		public SingleSkipPattern skipPatternForActuatorEndpointsDifferentPort(
+				final ServerProperties serverProperties,
+				final WebEndpointProperties webEndpointProperties,
+				final EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier) {
+			return () -> getEndpointsPatterns(null, webEndpointProperties, endpointsSupplier);
 		}
-
 	}
 
 	@Configuration
diff --git a/spring-cloud-sleuth-core/src/test/java/org/springframework/cloud/sleuth/instrument/web/SkipPatternProviderConfigTest.java b/spring-cloud-sleuth-core/src/test/java/org/springframework/cloud/sleuth/instrument/web/SkipPatternProviderConfigTest.java
index 6dbab83f2..abf8361f2 100644
--- a/spring-cloud-sleuth-core/src/test/java/org/springframework/cloud/sleuth/instrument/web/SkipPatternProviderConfigTest.java
+++ b/spring-cloud-sleuth-core/src/test/java/org/springframework/cloud/sleuth/instrument/web/SkipPatternProviderConfigTest.java
@@ -88,7 +88,7 @@ public class SkipPatternProviderConfigTest {
 	public void should_return_empty_when_no_endpoints() {
 		EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier = Collections::emptyList;
 		Optional<Pattern> pattern = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
-				.skipPatternForActuatorEndpoints(new ServerProperties(),
+				.skipPatternForActuatorEndpointsSamePort(new ServerProperties(),
 						new WebEndpointProperties(), endpointsSupplier)
 				.skipPattern();
 
@@ -107,8 +107,7 @@ public class SkipPatternProviderConfigTest {
 		};
 
 		Optional<Pattern> pattern = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
-				.skipPatternForActuatorEndpoints(properties, webEndpointProperties,
-						endpointsSupplier)
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
 				.skipPattern();
 
 		then(pattern).isNotEmpty();
@@ -130,8 +129,7 @@ public class SkipPatternProviderConfigTest {
 		};
 
 		Optional<Pattern> pattern = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
-				.skipPatternForActuatorEndpoints(properties, webEndpointProperties,
-						endpointsSupplier)
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
 				.skipPattern();
 
 		then(pattern).isNotEmpty();
@@ -153,8 +151,7 @@ public class SkipPatternProviderConfigTest {
 		};
 
 		Optional<Pattern> pattern = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
-				.skipPatternForActuatorEndpoints(properties, webEndpointProperties,
-						endpointsSupplier)
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
 				.skipPattern();
 
 		then(pattern).isNotEmpty();
@@ -176,14 +173,103 @@ public class SkipPatternProviderConfigTest {
 		};
 
 		Optional<Pattern> pattern = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
-				.skipPatternForActuatorEndpoints(properties, webEndpointProperties,
-						endpointsSupplier)
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
 				.skipPattern();
 
 		then(pattern).isNotEmpty();
 		then(pattern.get().pattern()).isEqualTo("foo/(info|info/.*|health|health/.*)");
 	}
 
+	@Test
+	public void should_return_endpoints_with_actuator_context_path_set_to_root() {
+		WebEndpointProperties webEndpointProperties = new WebEndpointProperties();
+		webEndpointProperties.setBasePath("/");
+		ServerProperties properties = new ServerProperties();
+		properties.getServlet().setContextPath("foo");
+
+		EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier = () -> {
+			ExposableWebEndpoint infoEndpoint = createEndpoint("info");
+			ExposableWebEndpoint healthEndpoint = createEndpoint("health");
+
+			return Arrays.asList(infoEndpoint, healthEndpoint);
+		};
+
+		Optional<Pattern> patternDifferentPort = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
+				.skipPatternForActuatorEndpointsDifferentPort(properties, webEndpointProperties, endpointsSupplier)
+				.skipPattern();
+
+		then(patternDifferentPort).isNotEmpty();
+		then(patternDifferentPort.get().pattern()).isEqualTo("/(info|info/.*|health|health/.*)");
+		
+		Optional<Pattern> patternSamePort = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
+				.skipPattern();
+		
+		then(patternSamePort).isNotEmpty();
+		then(patternSamePort.get().pattern())
+		   		.isEqualTo("foo/(info|info/.*|health|health/.*)");
+	}
+
+	@Test
+	public void should_return_endpoints_with_actuator_context_path_only() {
+		WebEndpointProperties webEndpointProperties = new WebEndpointProperties();
+		webEndpointProperties.setBasePath("/mgt");
+		ServerProperties properties = new ServerProperties();
+		properties.getServlet().setContextPath("foo");
+
+		EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier = () -> {
+			ExposableWebEndpoint infoEndpoint = createEndpoint("info");
+			ExposableWebEndpoint healthEndpoint = createEndpoint("health");
+
+			return Arrays.asList(infoEndpoint, healthEndpoint);
+		};
+
+		Optional<Pattern> patternDifferentPort = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
+				.skipPatternForActuatorEndpointsDifferentPort(properties, webEndpointProperties, endpointsSupplier)
+				.skipPattern();
+
+		then(patternDifferentPort).isNotEmpty();
+		then(patternDifferentPort.get().pattern())
+				.isEqualTo("/mgt/(info|info/.*|health|health/.*)");
+		
+		Optional<Pattern> patternSamePort = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
+				.skipPattern();
+		
+		then(patternSamePort).isNotEmpty();
+		then(patternSamePort.get().pattern())
+				.isEqualTo("foo/mgt/(info|info/.*|health|health/.*)");
+	}
+
+	@Test
+	public void should_return_endpoints_with_actuator_default_context_path() {
+		WebEndpointProperties webEndpointProperties = new WebEndpointProperties();
+		ServerProperties properties = new ServerProperties();
+		properties.getServlet().setContextPath("/foo");
+		properties.setPort(8080);
+
+		EndpointsSupplier<ExposableWebEndpoint> endpointsSupplier = () -> {
+			ExposableWebEndpoint infoEndpoint = createEndpoint("info");
+			ExposableWebEndpoint healthEndpoint = createEndpoint("health");
+
+			return Arrays.asList(infoEndpoint, healthEndpoint);
+		};
+
+		Optional<Pattern> patternDifferentPort = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
+				.skipPatternForActuatorEndpointsDifferentPort(properties, webEndpointProperties, endpointsSupplier)
+				.skipPattern();
+
+		then(patternDifferentPort).isNotEmpty();
+		then(patternDifferentPort.get().pattern()).isEqualTo("/actuator/(info|info/.*|health|health/.*)");
+		
+		Optional<Pattern> patternSamePort = new TraceWebAutoConfiguration.ActuatorSkipPatternProviderConfig()
+				.skipPatternForActuatorEndpointsSamePort(properties, webEndpointProperties, endpointsSupplier)
+				.skipPattern();
+
+		then(patternSamePort).isNotEmpty();
+		then(patternSamePort.get().pattern()).isEqualTo("/foo/actuator/(info|info/.*|health|health/.*)");
+	}
+
 	@Test
 	public void should_combine_skip_patterns_from_list() throws Exception {
 		TraceWebAutoConfiguration configuration = new TraceWebAutoConfiguration();