diff --git a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/TarLayoutWriter.java b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/TarLayoutWriter.java
index 3eddff38b2..66856ad034 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/TarLayoutWriter.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/TarLayoutWriter.java
@@ -39,6 +39,7 @@ class TarLayoutWriter implements Layout, Closeable {
 
 	TarLayoutWriter(OutputStream outputStream) {
 		this.outputStream = new TarArchiveOutputStream(outputStream);
+		this.outputStream.setLongFileMode(TarArchiveOutputStream.LONGFILE_POSIX);
 	}
 
 	@Override
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/ZipFileTarArchive.java b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/ZipFileTarArchive.java
index 525aa632d0..c6aea6c24c 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/ZipFileTarArchive.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/io/ZipFileTarArchive.java
@@ -61,6 +61,7 @@ public class ZipFileTarArchive implements TarArchive {
 	@Override
 	public void writeTo(OutputStream outputStream) throws IOException {
 		TarArchiveOutputStream tar = new TarArchiveOutputStream(outputStream);
+		tar.setLongFileMode(TarArchiveOutputStream.LONGFILE_POSIX);
 		try (ZipFile zipFile = new ZipFile(this.zip)) {
 			Enumeration<ZipArchiveEntry> entries = zipFile.getEntries();
 			while (entries.hasMoreElements()) {
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java b/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java
index b904d0384a..59c445e5e5 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java
@@ -20,6 +20,10 @@ import java.io.File;
 import java.io.FileWriter;
 import java.io.IOException;
 import java.io.PrintWriter;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.nio.file.Paths;
+import java.util.Random;
 
 import org.gradle.testkit.runner.BuildResult;
 import org.gradle.testkit.runner.TaskOutcome;
@@ -51,6 +55,7 @@ class BootBuildImageIntegrationTests {
 	@TestTemplate
 	void bootBuildImageBuildsImage() throws IOException {
 		writeMainClass();
+		writeLongNameResource();
 		BuildResult result = this.gradleBuild.build("bootBuildImage");
 		assertThat(result.task(":bootBuildImage").getOutcome()).isEqualTo(TaskOutcome.SUCCESS);
 		ImageReference imageReference = ImageReference.of(ImageName.of(this.gradleBuild.getProjectDir().getName()));
@@ -87,4 +92,18 @@ class BootBuildImageIntegrationTests {
 		}
 	}
 
+	private void writeLongNameResource() {
+		StringBuilder name = new StringBuilder();
+		new Random().ints('a', 'z' + 1).limit(128).forEach((i) -> name.append((char) i));
+		try {
+			Path path = this.gradleBuild.getProjectDir().toPath()
+					.resolve(Paths.get("src", "main", "resources", name.toString()));
+			Files.createDirectories(path.getParent());
+			Files.createFile(path);
+		}
+		catch (IOException ex) {
+			throw new RuntimeException(ex);
+		}
+	}
+
 }
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java
index aa898f6b81..889bcda38f 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java
@@ -18,6 +18,10 @@ package org.springframework.boot.maven;
 
 import java.io.File;
 import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.nio.file.Paths;
+import java.util.Random;
 
 import org.junit.jupiter.api.TestTemplate;
 import org.junit.jupiter.api.extension.ExtendWith;
@@ -42,7 +46,7 @@ public class BuildImageTests extends AbstractArchiveIntegrationTests {
 
 	@TestTemplate
 	void whenBuildImageIsInvokedWithoutRepackageTheArchiveIsRepackagedOnTheFly(MavenBuild mavenBuild) {
-		mavenBuild.project("build-image").goals("package").execute((project) -> {
+		mavenBuild.project("build-image").goals("package").prepare(this::writeLongNameResource).execute((project) -> {
 			File jar = new File(project, "target/build-image-0.0.1.BUILD-SNAPSHOT.jar");
 			assertThat(jar).isFile();
 			File original = new File(project, "target/build-image-0.0.1.BUILD-SNAPSHOT.jar.original");
@@ -79,6 +83,19 @@ public class BuildImageTests extends AbstractArchiveIntegrationTests {
 		});
 	}
 
+	private void writeLongNameResource(File project) {
+		StringBuilder name = new StringBuilder();
+		new Random().ints('a', 'z' + 1).limit(128).forEach((i) -> name.append((char) i));
+		try {
+			Path path = project.toPath().resolve(Paths.get("src", "main", "resources", name.toString()));
+			Files.createDirectories(path.getParent());
+			Files.createFile(path);
+		}
+		catch (IOException ex) {
+			throw new RuntimeException(ex);
+		}
+	}
+
 	private void removeImage(ImageReference imageReference) {
 		try {
 			new DockerApi().image().remove(imageReference, false);
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/MavenBuild.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/MavenBuild.java
index 7c1609b34e..145c5a1354 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/MavenBuild.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/MavenBuild.java
@@ -70,6 +70,8 @@ class MavenBuild {
 
 	private final Properties properties = new Properties();
 
+	private Consumer<File> preparation;
+
 	private File projectDir;
 
 	MavenBuild(File home) {
@@ -109,6 +111,11 @@ class MavenBuild {
 		return this;
 	}
 
+	MavenBuild prepare(Consumer<File> callback) {
+		this.preparation = callback;
+		return this;
+	}
+
 	void execute(Consumer<File> callback) {
 		Invoker invoker = new DefaultInvoker();
 		invoker.setMavenHome(this.home);
@@ -158,6 +165,9 @@ class MavenBuild {
 			request.setBatchMode(true);
 			File target = new File(this.temp, "target");
 			target.mkdirs();
+			if (this.preparation != null) {
+				this.preparation.accept(this.temp);
+			}
 			File buildLogFile = new File(target, "build.log");
 			try (PrintWriter buildLog = new PrintWriter(new FileWriter(buildLogFile))) {
 				request.setOutputHandler(new InvocationOutputHandler() {
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/main/java/org/springframework/boot/maven/BuildImageMojo.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/main/java/org/springframework/boot/maven/BuildImageMojo.java
index 0c88aaa2b8..795af32b97 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/main/java/org/springframework/boot/maven/BuildImageMojo.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/main/java/org/springframework/boot/maven/BuildImageMojo.java
@@ -215,6 +215,7 @@ public class BuildImageMojo extends AbstractPackagerMojo {
 		@Override
 		public void writeTo(OutputStream outputStream) throws IOException {
 			TarArchiveOutputStream tar = new TarArchiveOutputStream(outputStream);
+			tar.setLongFileMode(TarArchiveOutputStream.LONGFILE_POSIX);
 			this.packager.packageImage(this.libraries, (entry, entryWriter) -> write(entry, entryWriter, tar));
 		}