diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/ApplicationBuilder.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/ApplicationBuilder.java
index cb8c483998..198c8ec420 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/ApplicationBuilder.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/ApplicationBuilder.java
@@ -98,10 +98,12 @@ class ApplicationBuilder {
 			resourcesJarStream.putNextEntry(new ZipEntry("META-INF/resources/nested-meta-inf-resource.txt"));
 			resourcesJarStream.write("nested".getBytes());
 			resourcesJarStream.closeEntry();
-			resourcesJarStream.putNextEntry(
-					new ZipEntry("META-INF/resources/nested-reserved-!#$%&()*+,:=?@[]-meta-inf-resource.txt"));
-			resourcesJarStream.write("encoded-name".getBytes());
-			resourcesJarStream.closeEntry();
+			if (!isWindows()) {
+				resourcesJarStream.putNextEntry(
+						new ZipEntry("META-INF/resources/nested-reserved-!#$%&()*+,:=?@[]-meta-inf-resource.txt"));
+				resourcesJarStream.write("encoded-name".getBytes());
+				resourcesJarStream.closeEntry();
+			}
 			return resourcesJar;
 		}
 	}
@@ -162,4 +164,8 @@ class ApplicationBuilder {
 		assertThat(execute.getExitCode()).isEqualTo(0);
 	}
 
+	private boolean isWindows() {
+		return File.separatorChar == '\\';
+	}
+
 }
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarDevelopmentIntegrationTests.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarDevelopmentIntegrationTests.java
index 3e08be3e0c..d6a7540f4c 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarDevelopmentIntegrationTests.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarDevelopmentIntegrationTests.java
@@ -17,6 +17,8 @@
 package org.springframework.boot.context.embedded;
 
 import org.junit.jupiter.api.TestTemplate;
+import org.junit.jupiter.api.condition.DisabledOnOs;
+import org.junit.jupiter.api.condition.OS;
 
 import org.springframework.http.HttpStatus;
 import org.springframework.http.ResponseEntity;
@@ -41,6 +43,7 @@ public class EmbeddedServletContainerJarDevelopmentIntegrationTests {
 	}
 
 	@TestTemplate
+	@DisabledOnOs(OS.WINDOWS)
 	public void metaInfResourceFromDependencyWithNameThatContainsReservedCharactersIsAvailableViaHttp(
 			RestTemplate rest) {
 		ResponseEntity<String> entity = rest.getForEntity(
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarPackagingIntegrationTests.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarPackagingIntegrationTests.java
index 740bd2dd2c..d39ad4681a 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarPackagingIntegrationTests.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerJarPackagingIntegrationTests.java
@@ -17,6 +17,8 @@
 package org.springframework.boot.context.embedded;
 
 import org.junit.jupiter.api.TestTemplate;
+import org.junit.jupiter.api.condition.DisabledOnOs;
+import org.junit.jupiter.api.condition.OS;
 
 import org.springframework.http.HttpStatus;
 import org.springframework.http.ResponseEntity;
@@ -41,6 +43,7 @@ public class EmbeddedServletContainerJarPackagingIntegrationTests {
 	}
 
 	@TestTemplate
+	@DisabledOnOs(OS.WINDOWS)
 	public void nestedMetaInfResourceWithNameThatContainsReservedCharactersIsAvailableViaHttp(RestTemplate rest) {
 		ResponseEntity<String> entity = rest.getForEntity(
 				"/nested-reserved-%21%23%24%25%26%28%29%2A%2B%2C%3A%3D%3F%40%5B%5D-meta-inf-resource.txt",
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarDevelopmentIntegrationTests.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarDevelopmentIntegrationTests.java
index 14129dfcb4..1ded7aeeef 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarDevelopmentIntegrationTests.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarDevelopmentIntegrationTests.java
@@ -24,6 +24,8 @@ import java.util.List;
 import java.util.stream.Collectors;
 
 import org.junit.jupiter.api.TestTemplate;
+import org.junit.jupiter.api.condition.DisabledOnOs;
+import org.junit.jupiter.api.condition.OS;
 
 import org.springframework.http.HttpStatus;
 import org.springframework.http.ResponseEntity;
@@ -48,6 +50,7 @@ public class EmbeddedServletContainerWarDevelopmentIntegrationTests {
 	}
 
 	@TestTemplate
+	@DisabledOnOs(OS.WINDOWS)
 	public void metaInfResourceFromDependencyWithNameThatContainsReservedCharactersIsAvailableViaHttp(
 			RestTemplate rest) {
 		ResponseEntity<String> entity = rest.getForEntity(
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarPackagingIntegrationTests.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarPackagingIntegrationTests.java
index bd7cc699f5..4f557e0a83 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarPackagingIntegrationTests.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-server-tests/src/test/java/org/springframework/boot/context/embedded/EmbeddedServletContainerWarPackagingIntegrationTests.java
@@ -24,6 +24,8 @@ import java.util.List;
 import java.util.stream.Collectors;
 
 import org.junit.jupiter.api.TestTemplate;
+import org.junit.jupiter.api.condition.DisabledOnOs;
+import org.junit.jupiter.api.condition.OS;
 
 import org.springframework.http.HttpStatus;
 import org.springframework.http.ResponseEntity;
@@ -48,6 +50,7 @@ public class EmbeddedServletContainerWarPackagingIntegrationTests {
 	}
 
 	@TestTemplate
+	@DisabledOnOs(OS.WINDOWS)
 	public void nestedMetaInfResourceWithNameThatContainsReservedCharactersIsAvailableViaHttp(RestTemplate rest) {
 		ResponseEntity<String> entity = rest.getForEntity(
 				"/nested-reserved-%21%23%24%25%26%28%29%2A%2B%2C%3A%3D%3F%40%5B%5D-meta-inf-resource.txt",