diff --git a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
index 56d89c2acd..fa171d6718 100644
--- a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
+++ b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/web/ServerProperties.java
@@ -483,10 +483,20 @@ public class ServerProperties implements EmbeddedServletContainerCustomizer, Ord
 					if (handler instanceof AbstractHttp11Protocol) {
 						@SuppressWarnings("rawtypes")
 						AbstractHttp11Protocol protocol = (AbstractHttp11Protocol) handler;
-						protocol.setCompression(Tomcat.this.compression);
+						protocol.setCompression(coerceCompression(Tomcat.this.compression));
 						protocol.setCompressableMimeTypes(Tomcat.this.compressableMimeTypes);
 					}
 				}
+
+				private String coerceCompression(String compression) {
+					if (Boolean.toString(true).equals(compression)) {
+						return "on";
+					}
+					else if (Boolean.toString(false).equals(compression)) {
+						return "off";
+					}
+					return compression;
+				}
 			});
 
 			if (this.accessLogEnabled) {
diff --git a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
index bd2a13d065..5ce1f3d812 100644
--- a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
+++ b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/web/ServerPropertiesTests.java
@@ -31,6 +31,8 @@ import org.springframework.boot.context.embedded.ConfigurableEmbeddedServletCont
 import org.springframework.boot.context.embedded.tomcat.TomcatEmbeddedServletContainer;
 import org.springframework.boot.context.embedded.tomcat.TomcatEmbeddedServletContainerFactory;
 
+import static org.hamcrest.Matchers.equalTo;
+import static org.hamcrest.Matchers.is;
 import static org.hamcrest.core.IsInstanceOf.instanceOf;
 import static org.junit.Assert.assertEquals;
 import static org.junit.Assert.assertFalse;
@@ -197,9 +199,26 @@ public class ServerPropertiesTests {
 
 	@Test
 	public void customTomcatCompression() throws Exception {
+		assertThat("on", is(equalTo(configureCompression("on"))));
+	}
+
+	@Test
+	public void disableTomcatCompressionWithYaml() throws Exception {
+		// YAML interprets "off" as false, check that it's mapped back to off
+		assertThat("off", is(equalTo(configureCompression("false"))));
+	}
+
+	@Test
+	public void enableTomcatCompressionWithYaml() throws Exception {
+		// YAML interprets "on" as true, check that it's mapped back to on
+		assertThat("on", is(equalTo(configureCompression("true"))));
+	}
+
+	@Test
+	public void customTomcatCompressableMimeTypes() throws Exception {
 		Map<String, String> map = new HashMap<String, String>();
 		map.put("server.port", "0");
-		map.put("server.tomcat.compression", "on");
+		map.put("server.tomcat.compressableMimeTypes", "application/foo");
 		bindProperties(map);
 
 		TomcatEmbeddedServletContainerFactory factory = new TomcatEmbeddedServletContainerFactory();
@@ -211,18 +230,23 @@ public class ServerPropertiesTests {
 		try {
 			AbstractHttp11Protocol<?> protocol = (AbstractHttp11Protocol<?>) container
 					.getTomcat().getConnector().getProtocolHandler();
-			assertEquals("on", protocol.getCompression());
+			assertEquals("application/foo", protocol.getCompressableMimeTypes());
 		}
 		finally {
 			container.stop();
 		}
 	}
 
-	@Test
-	public void customTomcatCompressableMimeTypes() throws Exception {
+	private void bindProperties(Map<String, String> map) {
+		new RelaxedDataBinder(this.properties, "server").bind(new MutablePropertyValues(
+				map));
+	}
+
+	private String configureCompression(String compression) {
 		Map<String, String> map = new HashMap<String, String>();
 		map.put("server.port", "0");
-		map.put("server.tomcat.compressableMimeTypes", "application/foo");
+		// YAML interprets "on" as true
+		map.put("server.tomcat.compression", compression);
 		bindProperties(map);
 
 		TomcatEmbeddedServletContainerFactory factory = new TomcatEmbeddedServletContainerFactory();
@@ -234,16 +258,11 @@ public class ServerPropertiesTests {
 		try {
 			AbstractHttp11Protocol<?> protocol = (AbstractHttp11Protocol<?>) container
 					.getTomcat().getConnector().getProtocolHandler();
-			assertEquals("application/foo", protocol.getCompressableMimeTypes());
+			return protocol.getCompression();
 		}
 		finally {
 			container.stop();
 		}
 	}
 
-	private void bindProperties(Map<String, String> map) {
-		new RelaxedDataBinder(this.properties, "server").bind(new MutablePropertyValues(
-				map));
-	}
-
 }