diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java
index 65450ce395..81386386f9 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFile.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2022 the original author or authors.
+ * Copyright 2012-2021 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.
@@ -128,6 +128,9 @@ public class JarFile extends AbstractJarFile implements Iterable<java.util.jar.J
 	private JarFile(RandomAccessDataFile rootFile, String pathFromRoot, RandomAccessData data, JarEntryFilter filter,
 			JarFileType type, Supplier<Manifest> manifestSupplier) throws IOException {
 		super(rootFile.getFile());
+		if (System.getSecurityManager() == null) {
+			super.close();
+		}
 		this.rootFile = rootFile;
 		this.pathFromRoot = pathFromRoot;
 		CentralDirectoryParser parser = new CentralDirectoryParser();
@@ -139,7 +142,8 @@ public class JarFile extends AbstractJarFile implements Iterable<java.util.jar.J
 		}
 		catch (RuntimeException ex) {
 			try {
-				close();
+				this.rootFile.close();
+				super.close();
 			}
 			catch (IOException ioex) {
 			}
@@ -184,13 +188,8 @@ public class JarFile extends AbstractJarFile implements Iterable<java.util.jar.J
 	JarFileWrapper getWrapper() throws IOException {
 		JarFileWrapper wrapper = this.wrapper;
 		if (wrapper == null) {
-			synchronized (this) {
-				if (this.wrapper != null) {
-					return this.wrapper;
-				}
-				wrapper = new JarFileWrapper(this);
-				this.wrapper = wrapper;
-			}
+			wrapper = new JarFileWrapper(this);
+			this.wrapper = wrapper;
 		}
 		return wrapper;
 	}
@@ -356,13 +355,11 @@ public class JarFile extends AbstractJarFile implements Iterable<java.util.jar.J
 		if (this.closed) {
 			return;
 		}
-		synchronized (this) {
-			super.close();
-			if (this.type == JarFileType.DIRECT) {
-				this.rootFile.close();
-			}
-			this.closed = true;
+		super.close();
+		if (this.type == JarFileType.DIRECT) {
+			this.rootFile.close();
 		}
+		this.closed = true;
 	}
 
 	private void ensureOpen() {
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileWrapper.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileWrapper.java
index d5c2f2ca47..ebc8979855 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileWrapper.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarFileWrapper.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2022 the original author or authors.
+ * Copyright 2012-2021 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.
@@ -40,6 +40,9 @@ class JarFileWrapper extends AbstractJarFile {
 	JarFileWrapper(JarFile parent) throws IOException {
 		super(parent.getRootJarFile().getFile());
 		this.parent = parent;
+		if (System.getSecurityManager() == null) {
+			super.close();
+		}
 	}
 
 	@Override
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarURLConnection.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarURLConnection.java
index a7ba899231..5e3a4f7a80 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarURLConnection.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/JarURLConnection.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2022 the original author or authors.
+ * Copyright 2012-2021 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.
@@ -18,7 +18,6 @@ package org.springframework.boot.loader.jar;
 
 import java.io.ByteArrayOutputStream;
 import java.io.FileNotFoundException;
-import java.io.FilterInputStream;
 import java.io.IOException;
 import java.io.InputStream;
 import java.io.UnsupportedEncodingException;
@@ -166,7 +165,7 @@ final class JarURLConnection extends java.net.JarURLConnection {
 		if (inputStream == null) {
 			throwFileNotFound(this.jarEntryName, this.jarFile);
 		}
-		return new ConnectionInputStream(inputStream);
+		return inputStream;
 	}
 
 	private void throwFileNotFound(Object entry, AbstractJarFile jarFile) throws FileNotFoundException {
@@ -291,19 +290,6 @@ final class JarURLConnection extends java.net.JarURLConnection {
 		return new JarURLConnection(null, jarFile, jarEntryName);
 	}
 
-	private class ConnectionInputStream extends FilterInputStream {
-
-		ConnectionInputStream(InputStream in) {
-			super(in);
-		}
-
-		@Override
-		public void close() throws IOException {
-			JarURLConnection.this.jarFile.close();
-		}
-
-	}
-
 	/**
 	 * A JarEntryName parsed from a URL String.
 	 */
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/JarFileWrapperTests.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/JarFileWrapperTests.java
index 6cc4eb28d2..7da6716b00 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/JarFileWrapperTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/JarFileWrapperTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2022 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.
@@ -61,7 +61,6 @@ class JarFileWrapperTests {
 	@AfterEach
 	void cleanup() throws Exception {
 		this.parent.close();
-		this.wrapper.close();
 	}
 
 	private File createTempJar(File temp) throws IOException {
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/build.gradle b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/build.gradle
index 8cb06000b4..7c4095f73b 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/build.gradle
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/build.gradle
@@ -14,8 +14,6 @@ dependencies {
 	app project(path: ":spring-boot-project:spring-boot-dependencies", configuration: "mavenRepository")
 	app project(path: ":spring-boot-project:spring-boot-tools:spring-boot-gradle-plugin", configuration: "mavenRepository")
 	app project(path: ":spring-boot-project:spring-boot-starters:spring-boot-starter-web", configuration: "mavenRepository")
-	app project(path: ":spring-boot-project:spring-boot-starters:spring-boot-starter", configuration: "mavenRepository")
-	app("org.bouncycastle:bcprov-jdk15on:1.70")
 
 	intTestImplementation(enforcedPlatform(project(":spring-boot-project:spring-boot-parent")))
 	intTestImplementation(project(":spring-boot-project:spring-boot-tools:spring-boot-test-support"))
@@ -41,18 +39,6 @@ task buildApp(type: GradleBuild) {
 	tasks  = ["build"]
 }
 
-task syncSignedJarUnpackAppSource(type: org.springframework.boot.build.SyncAppSource) {
-	sourceDirectory = file("spring-boot-loader-tests-signed-jar-unpack-app")
-	destinationDirectory = file("${buildDir}/spring-boot-loader-tests-signed-jar-unpack-app")
-}
-
-task buildSignedJarUnpackApp(type: GradleBuild) {
-	dependsOn syncSignedJarUnpackAppSource, syncMavenRepository
-	dir = "${buildDir}/spring-boot-loader-tests-signed-jar-unpack-app"
-	startParameter.buildCacheEnabled = false
-	tasks  = ["build"]
-}
-
 intTest {
-	dependsOn buildApp, buildSignedJarUnpackApp
+	dependsOn buildApp
 }
\ No newline at end of file
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/build.gradle b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/build.gradle
deleted file mode 100644
index 88c4a0e3d8..0000000000
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/build.gradle
+++ /dev/null
@@ -1,22 +0,0 @@
-plugins {
-	id "java"
-	id "org.springframework.boot"
-}
-
-apply plugin: "io.spring.dependency-management"
-
-repositories {
-	maven { url "file:${rootDir}/../int-test-maven-repository"}
-	mavenCentral()
-	maven { url "https://repo.spring.io/snapshot" }
-	maven { url "https://repo.spring.io/milestone" }
-}
-
-dependencies {
-	implementation("org.springframework.boot:spring-boot-starter")
-	implementation("org.bouncycastle:bcprov-jdk18on:1.71")
-}
-
-bootJar {
-	requiresUnpack '**/bcprov-jdk18on-*.jar'
-}
\ No newline at end of file
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/settings.gradle b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/settings.gradle
deleted file mode 100644
index 06d9554ad0..0000000000
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/settings.gradle
+++ /dev/null
@@ -1,15 +0,0 @@
-pluginManagement {
-	repositories {
-		maven { url "file:${rootDir}/../int-test-maven-repository"}
-		mavenCentral()
-		maven { url "https://repo.spring.io/snapshot" }
-		maven { url "https://repo.spring.io/milestone" }
-	}
-	resolutionStrategy {
-		eachPlugin {
-			if (requested.id.id == "org.springframework.boot") {
-				useModule "org.springframework.boot:spring-boot-gradle-plugin:${requested.version}"
-			}
-		}
-	}
-}
\ No newline at end of file
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/src/main/java/org/springframework/boot/loaderapp/LoaderSignedJarTestApplication.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/src/main/java/org/springframework/boot/loaderapp/LoaderSignedJarTestApplication.java
deleted file mode 100644
index ce050ba586..0000000000
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar-unpack-app/src/main/java/org/springframework/boot/loaderapp/LoaderSignedJarTestApplication.java
+++ /dev/null
@@ -1,36 +0,0 @@
-/*
- * Copyright 2012-2022 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.
- * You may obtain a copy of the License at
- *
- *      https://www.apache.org/licenses/LICENSE-2.0
- *
- * Unless required by applicable law or agreed to in writing, software
- * distributed under the License is distributed on an "AS IS" BASIS,
- * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
- * See the License for the specific language governing permissions and
- * limitations under the License.
- */
-
-package org.springframework.boot.loaderapp;
-
-import java.security.Security;
-import javax.crypto.Cipher;
-import org.bouncycastle.jce.provider.BouncyCastleProvider;
-
-import org.springframework.boot.SpringApplication;
-import org.springframework.boot.autoconfigure.SpringBootApplication;
-
-@SpringBootApplication
-public class LoaderSignedJarTestApplication {
-
-	public static void main(String[] args) throws Exception {
-		Security.addProvider(new BouncyCastleProvider());
-		Cipher.getInstance("AES/CBC/PKCS5Padding","BC");
-		System.out.println("Legion of the Bouncy Castle");
-		SpringApplication.run(LoaderSignedJarTestApplication.class, args);
-	}
-
-}
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/src/intTest/java/org/springframework/boot/loader/LoaderIntegrationTests.java b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/src/intTest/java/org/springframework/boot/loader/LoaderIntegrationTests.java
index e4bce38694..8aa27b2efd 100644
--- a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/src/intTest/java/org/springframework/boot/loader/LoaderIntegrationTests.java
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/src/intTest/java/org/springframework/boot/loader/LoaderIntegrationTests.java
@@ -51,7 +51,7 @@ class LoaderIntegrationTests {
 	@ParameterizedTest
 	@MethodSource("javaRuntimes")
 	void readUrlsWithoutWarning(JavaRuntime javaRuntime) {
-		try (GenericContainer<?> container = createContainer(javaRuntime, "spring-boot-loader-tests-app")) {
+		try (GenericContainer<?> container = createContainer(javaRuntime)) {
 			container.start();
 			System.out.println(this.output.toUtf8String());
 			assertThat(this.output.toUtf8String()).contains(">>>>> 287649 BYTES from").doesNotContain("WARNING:")
@@ -59,32 +59,17 @@ class LoaderIntegrationTests {
 		}
 	}
 
-	@ParameterizedTest
-	@MethodSource("javaRuntimes")
-	void runSignedJarWhenUnpacked(JavaRuntime javaRuntime) {
-		try (GenericContainer<?> container = createContainer(javaRuntime,
-				"spring-boot-loader-tests-signed-jar-unpack-app")) {
-			container.start();
-			System.out.println(this.output.toUtf8String());
-			assertThat(this.output.toUtf8String()).contains("Legion of the Bouncy Castle");
-		}
-	}
-
-	private GenericContainer<?> createContainer(JavaRuntime javaRuntime, String name) {
+	private GenericContainer<?> createContainer(JavaRuntime javaRuntime) {
 		return javaRuntime.getContainer().withLogConsumer(this.output)
-				.withCopyFileToContainer(findApplication(name), "/app.jar")
+				.withCopyFileToContainer(MountableFile.forHostPath(findApplication().toPath()), "/app.jar")
 				.withStartupCheckStrategy(new OneShotStartupCheckStrategy().withTimeout(Duration.ofMinutes(5)))
 				.withCommand("java", "-jar", "app.jar");
 	}
 
-	private MountableFile findApplication(String name) {
-		return MountableFile.forHostPath(findJarFile(name).toPath());
-	}
-
-	private File findJarFile(String name) {
-		String path = String.format("build/%1$s/build/libs/%1$s.jar", name);
-		File jar = new File(path);
-		Assert.state(jar.isFile(), () -> "Could not find " + path + ". Have you built it?");
+	private File findApplication() {
+		String name = String.format("build/%1$s/build/libs/%1$s.jar", "spring-boot-loader-tests-app");
+		File jar = new File(name);
+		Assert.state(jar.isFile(), () -> "Could not find " + name + ". Have you built it?");
 		return jar;
 	}