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 e287ed0a16a6..aa88c046b4ae 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
@@ -18,6 +18,8 @@ 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-jdk18on:1.76")
 
 	intTestImplementation(enforcedPlatform(project(":spring-boot-project:spring-boot-parent")))
 	intTestImplementation(project(":spring-boot-project:spring-boot-tools:spring-boot-test-support"))
@@ -43,6 +45,18 @@ task buildApp(type: GradleBuild) {
 	tasks  = ["build"]
 }
 
+task syncSignedJarAppSource(type: org.springframework.boot.build.SyncAppSource) {
+	sourceDirectory = file("spring-boot-loader-tests-signed-jar")
+	destinationDirectory = file("${buildDir}/spring-boot-loader-tests-signed-jar")
+}
+
+task buildSignedJarApp(type: GradleBuild) {
+	dependsOn syncSignedJarAppSource, syncMavenRepository
+	dir = "${buildDir}/spring-boot-loader-tests-signed-jar"
+	startParameter.buildCacheEnabled = false
+	tasks  = ["build"]
+}
+
 task downloadJdk(type: Download) {
 	def destFolder = new File(rootProject.buildDir, "downloads/jdk/oracle")
 	destFolder.mkdirs()
@@ -64,5 +78,5 @@ processIntTestResources {
 }
 
 intTest {
-	dependsOn buildApp
+	dependsOn buildApp, buildSignedJarApp
 }
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/build.gradle b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/build.gradle
new file mode 100644
index 000000000000..7ca8a2712496
--- /dev/null
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/build.gradle
@@ -0,0 +1,30 @@
+import org.springframework.boot.gradle.tasks.bundling.BootJar
+
+plugins {
+	id "java"
+	id "org.springframework.boot"
+}
+
+apply plugin: "io.spring.dependency-management"
+
+repositories {
+	maven { url "file:${rootDir}/../int-test-maven-repository"}
+	mavenCentral()
+	maven { url "https://repo.spring.io/snapshot" }
+	maven { url "https://repo.spring.io/milestone" }
+}
+
+dependencies {
+	implementation("org.springframework.boot:spring-boot-starter")
+	implementation("org.bouncycastle:bcprov-jdk18on:1.76")
+}
+
+tasks.register("bootJarUnpack", BootJar.class) {
+	mainClass = "org.springframework.boot.loaderapp.LoaderSignedJarTestApplication"
+	classpath = bootJar.classpath
+	requiresUnpack '**/bcprov-jdk18on-*.jar'
+	archiveClassifier.set("unpack")
+	targetJavaVersion = targetCompatibility
+}
+
+build.dependsOn bootJarUnpack
\ No newline at end of file
diff --git a/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/settings.gradle b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/settings.gradle
new file mode 100644
index 000000000000..06d9554ad0d6
--- /dev/null
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/settings.gradle
@@ -0,0 +1,15 @@
+pluginManagement {
+	repositories {
+		maven { url "file:${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/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/src/main/java/org/springframework/boot/loaderapp/LoaderSignedJarTestApplication.java
new file mode 100644
index 000000000000..627a6c3996d3
--- /dev/null
+++ b/spring-boot-tests/spring-boot-integration-tests/spring-boot-loader-tests/spring-boot-loader-tests-signed-jar/src/main/java/org/springframework/boot/loaderapp/LoaderSignedJarTestApplication.java
@@ -0,0 +1,36 @@
+/*
+ * Copyright 2012-2023 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 3e5c2f023e54..ac6592bc9d6d 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
@@ -37,6 +37,7 @@
 import org.springframework.util.Assert;
 
 import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assumptions.assumeThat;
 
 /**
  * Integration tests loader that supports fat jars.
@@ -52,7 +53,7 @@ class LoaderIntegrationTests {
 	@ParameterizedTest
 	@MethodSource("javaRuntimes")
 	void readUrlsWithoutWarning(JavaRuntime javaRuntime) {
-		try (GenericContainer<?> container = createContainer(javaRuntime)) {
+		try (GenericContainer<?> container = createContainer(javaRuntime, "spring-boot-loader-tests-app", null)) {
 			container.start();
 			System.out.println(this.output.toUtf8String());
 			assertThat(this.output.toUtf8String()).contains(">>>>> 287649 BYTES from")
@@ -62,18 +63,46 @@ void readUrlsWithoutWarning(JavaRuntime javaRuntime) {
 		}
 	}
 
-	private GenericContainer<?> createContainer(JavaRuntime javaRuntime) {
+	@ParameterizedTest
+	@MethodSource("javaRuntimes")
+	void runSignedJar(JavaRuntime javaRuntime) {
+		assumeThat(javaRuntime.toString()).isNotEqualTo("Oracle JDK 17"); // gh-28837
+		try (GenericContainer<?> container = createContainer(javaRuntime, "spring-boot-loader-tests-signed-jar",
+				null)) {
+			container.start();
+			System.out.println(this.output.toUtf8String());
+			assertThat(this.output.toUtf8String()).contains("Legion of the Bouncy Castle");
+		}
+	}
+
+	@ParameterizedTest
+	@MethodSource("javaRuntimes")
+	void runSignedJarWhenUnpack(JavaRuntime javaRuntime) {
+		try (GenericContainer<?> container = createContainer(javaRuntime, "spring-boot-loader-tests-signed-jar",
+				"unpack")) {
+			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, String classifier) {
 		return javaRuntime.getContainer()
 			.withLogConsumer(this.output)
-			.withCopyFileToContainer(MountableFile.forHostPath(findApplication().toPath()), "/app.jar")
+			.withCopyFileToContainer(findApplication(name, classifier), "/app.jar")
 			.withStartupCheckStrategy(new OneShotStartupCheckStrategy().withTimeout(Duration.ofMinutes(5)))
 			.withCommand("java", "-jar", "app.jar");
 	}
 
-	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?");
+	private MountableFile findApplication(String name, String classifier) {
+		return MountableFile.forHostPath(findJarFile(name, classifier).toPath());
+	}
+
+	private File findJarFile(String name, String classifier) {
+		classifier = (classifier != null) ? "-" + classifier : "";
+		String path = String.format("build/%1$s/build/libs/%1$s%2$s.jar", name, classifier);
+		File jar = new File(path);
+		Assert.state(jar.isFile(), () -> "Could not find " + path + ". Have you built it?");
 		return jar;
 	}