diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Packager.java b/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Packager.java
index 7f5edd7476..09fb3b9df6 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Packager.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Packager.java
@@ -24,6 +24,7 @@ import java.util.LinkedHashMap;
 import java.util.List;
 import java.util.Map;
 import java.util.Map.Entry;
+import java.util.TreeMap;
 import java.util.concurrent.TimeUnit;
 import java.util.function.Function;
 import java.util.jar.Attributes;
@@ -192,8 +193,13 @@ public abstract class Packager {
 	}
 
 	protected final void write(JarFile sourceJar, Libraries libraries, AbstractJarWriter writer) throws IOException {
+		write(sourceJar, libraries, writer, false);
+	}
+
+	protected final void write(JarFile sourceJar, Libraries libraries, AbstractJarWriter writer,
+			boolean ensureReproducibleBuild) throws IOException {
 		Assert.notNull(libraries, "Libraries must not be null");
-		write(sourceJar, writer, new PackagedLibraries(libraries));
+		write(sourceJar, writer, new PackagedLibraries(libraries, ensureReproducibleBuild));
 	}
 
 	private void write(JarFile sourceJar, AbstractJarWriter writer, PackagedLibraries libraries) throws IOException {
@@ -454,18 +460,18 @@ public abstract class Packager {
 	}
 
 	/**
-	 * An {@link UnpackHandler} that determines that an entry needs to be unpacked if a
-	 * library that requires unpacking has a matching entry name.
+	 * Libraries that should be packaged into the archive.
 	 */
 	private final class PackagedLibraries {
 
-		private final Map<String, Library> libraries = new LinkedHashMap<>();
+		private final Map<String, Library> libraries;
 
 		private final UnpackHandler unpackHandler;
 
 		private final Function<JarEntry, Library> libraryLookup;
 
-		PackagedLibraries(Libraries libraries) throws IOException {
+		PackagedLibraries(Libraries libraries, boolean ensureReproducibleBuild) throws IOException {
+			this.libraries = (ensureReproducibleBuild) ? new TreeMap<>() : new LinkedHashMap<>();
 			libraries.doWithLibraries((library) -> {
 				if (isZip(library::openStream)) {
 					addLibrary(library);
@@ -521,6 +527,10 @@ public abstract class Packager {
 			writer.writeIndexFile(layout.getClasspathIndexFileLocation(), names);
 		}
 
+		/**
+		 * An {@link UnpackHandler} that determines that an entry needs to be unpacked if
+		 * a library that requires unpacking has a matching entry name.
+		 */
 		private class PackagedLibrariesUnpackHandler implements UnpackHandler {
 
 			@Override
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Repackager.java b/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Repackager.java
index e5d66796ac..329b7ce90c 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Repackager.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader-tools/src/main/java/org/springframework/boot/loader/tools/Repackager.java
@@ -141,7 +141,7 @@ public class Repackager extends Packager {
 	private void repackage(JarFile sourceJar, File destination, Libraries libraries, LaunchScript launchScript,
 			FileTime lastModifiedTime) throws IOException {
 		try (JarWriter writer = new JarWriter(destination, launchScript, lastModifiedTime)) {
-			write(sourceJar, libraries, writer);
+			write(sourceJar, libraries, writer, lastModifiedTime != null);
 		}
 		if (lastModifiedTime != null) {
 			destination.setLastModified(lastModifiedTime.toMillis());
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/AbstractArchiveIntegrationTests.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/AbstractArchiveIntegrationTests.java
index 05cc9a7764..5232a76a15 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/AbstractArchiveIntegrationTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/AbstractArchiveIntegrationTests.java
@@ -30,11 +30,13 @@ import java.util.function.Consumer;
 import java.util.jar.JarEntry;
 import java.util.jar.JarFile;
 import java.util.jar.Manifest;
+import java.util.stream.Collectors;
 import java.util.stream.Stream;
 import java.util.zip.ZipEntry;
 
 import org.assertj.core.api.AbstractAssert;
 import org.assertj.core.api.AssertProvider;
+import org.assertj.core.api.ListAssert;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.contentOf;
@@ -43,6 +45,7 @@ import static org.assertj.core.api.Assertions.contentOf;
  * Base class for archive (jar or war) related Maven plugin integration tests.
  *
  * @author Andy Wilkinson
+ * @author Scott Frederick
  */
 abstract class AbstractArchiveIntegrationTests {
 
@@ -155,6 +158,15 @@ abstract class AbstractArchiveIntegrationTests {
 			return this;
 		}
 
+		ListAssert<String> entryNamesInPath(String path) {
+			List<String> matches = new ArrayList<>();
+			withJarFile((jarFile) -> withEntries(jarFile,
+					(entries) -> matches.addAll(entries.map(ZipEntry::getName)
+							.filter((name) -> name.startsWith(path) && name.length() > path.length())
+							.collect(Collectors.toList()))));
+			return new ListAssert<>(matches);
+		}
+
 		JarAssert manifest(Consumer<ManifestAssert> consumer) {
 			withJarFile((jarFile) -> {
 				try {
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/JarIntegrationTests.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/JarIntegrationTests.java
index c85ecc9c88..a6e4b3157d 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/JarIntegrationTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/JarIntegrationTests.java
@@ -18,6 +18,7 @@ package org.springframework.boot.maven;
 
 import java.io.File;
 import java.io.IOException;
+import java.util.Arrays;
 import java.util.List;
 import java.util.Map;
 import java.util.concurrent.atomic.AtomicReference;
@@ -38,6 +39,7 @@ import static org.assertj.core.api.Assertions.assertThat;
  *
  * @author Andy Wilkinson
  * @author Madhura Bhave
+ * @author Scott Frederick
  */
 @ExtendWith(MavenBuildExtension.class)
 class JarIntegrationTests extends AbstractArchiveIntegrationTests {
@@ -394,4 +396,31 @@ class JarIntegrationTests extends AbstractArchiveIntegrationTests {
 		return jarHash.get();
 	}
 
+	@TestTemplate
+	void whenJarIsRepackagedWithDefaultsThenLibrariesAreNotSorted(MavenBuild mavenBuild) throws InterruptedException {
+		mavenBuild.project("jar").execute((project) -> {
+			File repackaged = new File(project, "target/jar-0.0.1.BUILD-SNAPSHOT.jar");
+			List<String> unsortedLibs = Arrays.asList("BOOT-INF/lib/spring-context", "BOOT-INF/lib/spring-aop",
+					"BOOT-INF/lib/spring-beans", "BOOT-INF/lib/spring-core", "BOOT-INF/lib/spring-jcl",
+					"BOOT-INF/lib/spring-expression", "BOOT-INF/lib/jakarta.servlet-api",
+					"BOOT-INF/lib/spring-boot-jarmode-layertools");
+			assertThat(jar(repackaged)).entryNamesInPath("BOOT-INF/lib/").zipSatisfy(unsortedLibs,
+					(String jarLib, String expectedLib) -> assertThat(jarLib).startsWith(expectedLib));
+		});
+	}
+
+	@TestTemplate
+	void whenJarIsRepackagedWithOutputTimestampConfiguredThenLibrariesAreSorted(MavenBuild mavenBuild)
+			throws InterruptedException {
+		mavenBuild.project("jar-output-timestamp").execute((project) -> {
+			File repackaged = new File(project, "target/jar-output-timestamp-0.0.1.BUILD-SNAPSHOT.jar");
+			List<String> sortedLibs = Arrays.asList("BOOT-INF/lib/jakarta.servlet-api", "BOOT-INF/lib/spring-aop",
+					"BOOT-INF/lib/spring-beans", "BOOT-INF/lib/spring-boot-jarmode-layertools",
+					"BOOT-INF/lib/spring-context", "BOOT-INF/lib/spring-core", "BOOT-INF/lib/spring-expression",
+					"BOOT-INF/lib/spring-jcl");
+			assertThat(jar(repackaged)).entryNamesInPath("BOOT-INF/lib/").zipSatisfy(sortedLibs,
+					(String jarLib, String expectedLib) -> assertThat(jarLib).startsWith(expectedLib));
+		});
+	}
+
 }
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/WarIntegrationTests.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/WarIntegrationTests.java
index 6615cd1567..e32b6f58d0 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/WarIntegrationTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/WarIntegrationTests.java
@@ -19,6 +19,7 @@ package org.springframework.boot.maven;
 import java.io.File;
 import java.io.IOException;
 import java.util.ArrayList;
+import java.util.Arrays;
 import java.util.List;
 import java.util.Map;
 import java.util.concurrent.atomic.AtomicReference;
@@ -38,6 +39,7 @@ import static org.assertj.core.api.Assertions.assertThat;
  * Integration tests for the Maven plugin's war support.
  *
  * @author Andy Wilkinson
+ * @author Scott Frederick
  */
 @ExtendWith(MavenBuildExtension.class)
 class WarIntegrationTests extends AbstractArchiveIntegrationTests {
@@ -110,6 +112,36 @@ class WarIntegrationTests extends AbstractArchiveIntegrationTests {
 		return warHash.get();
 	}
 
+	@TestTemplate
+	void whenWarIsRepackagedWithDefaultsThenLibrariesAreNotSorted(MavenBuild mavenBuild) throws InterruptedException {
+		mavenBuild.project("war").execute((project) -> {
+			File repackaged = new File(project, "target/war-0.0.1.BUILD-SNAPSHOT.war");
+			List<String> unsortedLibs = Arrays.asList("WEB-INF/lib/spring-aop", "WEB-INF/lib/spring-beans",
+					"WEB-INF/lib/spring-expression", "WEB-INF/lib/spring-context", "WEB-INF/lib/spring-core",
+					"WEB-INF/lib/spring-jcl", "WEB-INF/lib/spring-boot-jarmode-layertools");
+			assertThat(jar(repackaged)).entryNamesInPath("WEB-INF/lib/").zipSatisfy(unsortedLibs,
+					(String jarLib, String expectedLib) -> assertThat(jarLib).startsWith(expectedLib));
+		});
+	}
+
+	@TestTemplate
+	void whenWarIsRepackagedWithOutputTimestampConfiguredThenLibrariesAreSorted(MavenBuild mavenBuild)
+			throws InterruptedException {
+		mavenBuild.project("war-output-timestamp").execute((project) -> {
+			File repackaged = new File(project, "target/war-output-timestamp-0.0.1.BUILD-SNAPSHOT.war");
+			List<String> sortedLibs = Arrays.asList(
+					// these libraries are copied from the original war, sorted when
+					// packaged by Maven
+					"WEB-INF/lib/spring-aop", "WEB-INF/lib/spring-beans", "WEB-INF/lib/spring-context",
+					"WEB-INF/lib/spring-core", "WEB-INF/lib/spring-expression", "WEB-INF/lib/spring-jcl",
+					// these libraries are contributed by Spring Boot repackaging, and
+					// sorted separately
+					"WEB-INF/lib/spring-boot-jarmode-layertools");
+			assertThat(jar(repackaged)).entryNamesInPath("WEB-INF/lib/").zipSatisfy(sortedLibs,
+					(String jarLib, String expectedLib) -> assertThat(jarLib).startsWith(expectedLib));
+		});
+	}
+
 	@TestTemplate
 	void whenADependencyHasSystemScopeAndInclusionOfSystemScopeDependenciesIsEnabledItIsIncludedInTheRepackagedJar(
 			MavenBuild mavenBuild) {