diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java
index e27fffd04dd..d174f2fc56a 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/JettyWebServer.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2019 the original author or authors.
+ * Copyright 2012-2020 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -20,6 +20,7 @@ import java.io.IOException;
 import java.net.BindException;
 import java.util.Arrays;
 import java.util.List;
+import java.util.Objects;
 import java.util.stream.Collectors;
 
 import org.apache.commons.logging.Log;
@@ -206,8 +207,18 @@ public class JettyWebServer implements WebServer {
 	}
 
 	private String getContextPath() {
-		return Arrays.stream(this.server.getHandlers()).filter(ContextHandler.class::isInstance)
-				.map(ContextHandler.class::cast).map(ContextHandler::getContextPath).collect(Collectors.joining(" "));
+		return Arrays.stream(this.server.getHandlers()).map(this::findContextHandler).filter(Objects::nonNull)
+				.map(ContextHandler::getContextPath).collect(Collectors.joining(" "));
+	}
+
+	private ContextHandler findContextHandler(Handler handler) {
+		while (handler instanceof HandlerWrapper) {
+			if (handler instanceof ContextHandler) {
+				return (ContextHandler) handler;
+			}
+			handler = ((HandlerWrapper) handler).getHandler();
+		}
+		return null;
 	}
 
 	private void handleDeferredInitialize(Handler... handlers) throws Exception {
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/AbstractJettyServletWebServerFactoryTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/AbstractJettyServletWebServerFactoryTests.java
index 4ed7c62367c..7032c59b3fe 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/AbstractJettyServletWebServerFactoryTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/AbstractJettyServletWebServerFactoryTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2019 the original author or authors.
+ * Copyright 2012-2020 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -24,7 +24,10 @@ import org.apache.jasper.servlet.JspServlet;
 import org.eclipse.jetty.server.ServerConnector;
 import org.eclipse.jetty.servlet.ServletHolder;
 import org.eclipse.jetty.webapp.WebAppContext;
+import org.junit.jupiter.api.Test;
 
+import org.springframework.boot.testsupport.system.CapturedOutput;
+import org.springframework.boot.web.server.Compression;
 import org.springframework.boot.web.server.PortInUseException;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactory;
 import org.springframework.boot.web.servlet.server.AbstractServletWebServerFactoryTests;
@@ -88,4 +91,16 @@ abstract class AbstractJettyServletWebServerFactoryTests extends AbstractServlet
 		this.handleExceptionCausedByBlockedPortOnPrimaryConnector(ex, blockedPort);
 	}
 
+	@Test
+	void contextPathIsLoggedOnStartupWhenCompressionIsEnabled(CapturedOutput output) {
+		AbstractServletWebServerFactory factory = getFactory();
+		factory.setContextPath("/custom");
+		Compression compression = new Compression();
+		compression.setEnabled(true);
+		factory.setCompression(compression);
+		this.webServer = factory.getWebServer(exampleServletRegistration());
+		this.webServer.start();
+		assertThat(output).containsOnlyOnce("with context path '/custom'");
+	}
+
 }