diff --git a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfiguration.java b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfiguration.java
index c19dcb24fd..51aaed9dc4 100644
--- a/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfiguration.java
+++ b/spring-boot-devtools/src/main/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfiguration.java
@@ -31,6 +31,7 @@ import org.springframework.boot.autoconfigure.condition.ConditionalOnClass;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnMissingBean;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnProperty;
 import org.springframework.boot.autoconfigure.security.SecurityProperties;
+import org.springframework.boot.autoconfigure.web.ServerProperties;
 import org.springframework.boot.context.properties.EnableConfigurationProperties;
 import org.springframework.boot.devtools.remote.server.AccessManager;
 import org.springframework.boot.devtools.remote.server.Dispatcher;
@@ -76,6 +77,9 @@ public class RemoteDevToolsAutoConfiguration {
 	@Autowired
 	private DevToolsProperties properties;
 
+	@Autowired
+	private ServerProperties serverProperties;
+
 	@Bean
 	@ConditionalOnMissingBean
 	public AccessManager remoteDevToolsAccessManager() {
@@ -87,8 +91,9 @@ public class RemoteDevToolsAutoConfiguration {
 	@Bean
 	public HandlerMapper remoteDevToolsHealthCheckHandlerMapper() {
 		Handler handler = new HttpStatusHandler();
-		return new UrlHandlerMapper(this.properties.getRemote().getContextPath(),
-				handler);
+		return new UrlHandlerMapper((this.serverProperties.getContextPath() == null ? ""
+				: this.serverProperties.getContextPath())
+				+ this.properties.getRemote().getContextPath(), handler);
 	}
 
 	@Bean
@@ -108,6 +113,9 @@ public class RemoteDevToolsAutoConfiguration {
 		@Autowired
 		private DevToolsProperties properties;
 
+		@Autowired
+		private ServerProperties serverProperties;
+
 		@Bean
 		@ConditionalOnMissingBean
 		public SourceFolderUrlFilter remoteRestartSourceFolderUrlFilter() {
@@ -124,7 +132,9 @@ public class RemoteDevToolsAutoConfiguration {
 		@Bean
 		@ConditionalOnMissingBean(name = "remoteRestartHanderMapper")
 		public UrlHandlerMapper remoteRestartHanderMapper(HttpRestartServer server) {
-			String url = this.properties.getRemote().getContextPath() + "/restart";
+			String url = (this.serverProperties.getContextPath() == null ? ""
+					: this.serverProperties.getContextPath())
+					+ this.properties.getRemote().getContextPath() + "/restart";
 			logger.warn("Listening for remote restart updates on " + url);
 			Handler handler = new HttpRestartServerHandler(server);
 			return new UrlHandlerMapper(url, handler);
@@ -141,11 +151,16 @@ public class RemoteDevToolsAutoConfiguration {
 		@Autowired
 		private DevToolsProperties properties;
 
+		@Autowired
+		private ServerProperties serverProperties;
+
 		@Bean
 		@ConditionalOnMissingBean(name = "remoteDebugHanderMapper")
 		public UrlHandlerMapper remoteDebugHanderMapper(
 				@Qualifier("remoteDebugHttpTunnelServer") HttpTunnelServer server) {
-			String url = this.properties.getRemote().getContextPath() + "/debug";
+			String url = (this.serverProperties.getContextPath() == null ? ""
+					: this.serverProperties.getContextPath())
+					+ this.properties.getRemote().getContextPath() + "/debug";
 			logger.warn("Listening for remote debug traffic on " + url);
 			Handler handler = new HttpTunnelServerHandler(server);
 			return new UrlHandlerMapper(url, handler);
diff --git a/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfigurationTests.java b/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfigurationTests.java
index 682f598016..acb2ad1c4e 100644
--- a/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfigurationTests.java
+++ b/spring-boot-devtools/src/test/java/org/springframework/boot/devtools/autoconfigure/RemoteDevToolsAutoConfigurationTests.java
@@ -137,6 +137,17 @@ public class RemoteDevToolsAutoConfigurationTests {
 		assertRestartInvoked(true);
 	}
 
+	@Test
+	public void invokeRestartWithCustomServerContextPath() throws Exception {
+		loadContext("spring.devtools.remote.secret:supersecret",
+				"server.context-path:/test");
+		DispatcherFilter filter = this.context.getBean(DispatcherFilter.class);
+		this.request.setRequestURI("/test" + DEFAULT_CONTEXT_PATH + "/restart");
+		this.request.addHeader(DEFAULT_SECRET_HEADER_NAME, "supersecret");
+		filter.doFilter(this.request, this.response, this.chain);
+		assertRestartInvoked(true);
+	}
+
 	@Test
 	public void disableRestart() throws Exception {
 		loadContext("spring.devtools.remote.secret:supersecret",
@@ -155,6 +166,17 @@ public class RemoteDevToolsAutoConfigurationTests {
 		assertTunnelInvoked(true);
 	}
 
+	@Test
+	public void invokeTunnelWithCustomServerContextPath() throws Exception {
+		loadContext("spring.devtools.remote.secret:supersecret",
+				"server.context-path:/test");
+		DispatcherFilter filter = this.context.getBean(DispatcherFilter.class);
+		this.request.setRequestURI("/test" + DEFAULT_CONTEXT_PATH + "/debug");
+		this.request.addHeader(DEFAULT_SECRET_HEADER_NAME, "supersecret");
+		filter.doFilter(this.request, this.response, this.chain);
+		assertTunnelInvoked(true);
+	}
+
 	@Test
 	public void invokeTunnelWithCustomHeaderName() throws Exception {
 		loadContext("spring.devtools.remote.secret:supersecret",
@@ -185,6 +207,18 @@ public class RemoteDevToolsAutoConfigurationTests {
 		assertThat(this.response.getStatus(), equalTo(200));
 	}
 
+	@Test
+	public void devToolsHealthWithCustomServerContextPathReturns200() throws Exception {
+		loadContext("spring.devtools.remote.secret:supersecret",
+				"server.context-path:/test");
+		DispatcherFilter filter = this.context.getBean(DispatcherFilter.class);
+		this.request.setRequestURI("/test" + DEFAULT_CONTEXT_PATH);
+		this.request.addHeader(DEFAULT_SECRET_HEADER_NAME, "supersecret");
+		this.response.setStatus(500);
+		filter.doFilter(this.request, this.response, this.chain);
+		assertThat(this.response.getStatus(), equalTo(200));
+	}
+
 	private void assertTunnelInvoked(boolean value) {
 		assertThat(this.context.getBean(MockHttpTunnelServer.class).invoked,
 				equalTo(value));