diff --git a/src/test/java/com/android/tools/r8/KotlinCompilerTool.java b/src/test/java/com/android/tools/r8/KotlinCompilerTool.java
index 61efff1..f830f0e 100644
--- a/src/test/java/com/android/tools/r8/KotlinCompilerTool.java
+++ b/src/test/java/com/android/tools/r8/KotlinCompilerTool.java
@@ -12,6 +12,7 @@
 import com.android.tools.r8.TestRuntime.CfRuntime;
 import com.android.tools.r8.ToolHelper.KotlinTargetVersion;
 import com.android.tools.r8.ToolHelper.ProcessResult;
+import com.android.tools.r8.utils.ArrayUtils;
 import com.android.tools.r8.utils.FileUtils;
 import com.android.tools.r8.utils.structural.Ordered;
 import java.io.IOException;
@@ -39,6 +40,10 @@
     KotlinCompilerVersion(String folder) {
       this.folder = folder;
     }
+
+    public static KotlinCompilerVersion latest() {
+      return ArrayUtils.last(values());
+    }
   }
 
   public static final class KotlinCompiler {
diff --git a/src/test/java/com/android/tools/r8/kotlin/metadata/MetadataFirstToLatestTest.java b/src/test/java/com/android/tools/r8/kotlin/metadata/MetadataFirstToLatestTest.java
new file mode 100644
index 0000000..c16c2f5
--- /dev/null
+++ b/src/test/java/com/android/tools/r8/kotlin/metadata/MetadataFirstToLatestTest.java
@@ -0,0 +1,135 @@
+// Copyright (c) 2021, the R8 project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+package com.android.tools.r8.kotlin.metadata;
+
+import static com.android.tools.r8.ToolHelper.getKotlinAnnotationJar;
+import static com.android.tools.r8.ToolHelper.getKotlinStdlibJar;
+import static org.hamcrest.CoreMatchers.equalTo;
+
+import com.android.tools.r8.KotlinCompilerTool.KotlinCompiler;
+import com.android.tools.r8.KotlinCompilerTool.KotlinCompilerVersion;
+import com.android.tools.r8.KotlinTestParameters;
+import com.android.tools.r8.TestParameters;
+import com.android.tools.r8.ToolHelper;
+import com.android.tools.r8.utils.DescriptorUtils;
+import com.android.tools.r8.utils.StringUtils;
+import java.nio.file.Path;
+import java.util.Collection;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+import org.junit.runners.Parameterized;
+
+/**
+ * Kotlin has limited support for metadata of older versions. In particular, kotlinc 1.5 has
+ * deprecated byte-code version which is expected by kotlinc 1.3. The expectation is that if we
+ * compile with kotlinc 1.3 and then compile with R8 with a new version of the kolin-metadata-jvm
+ * library, the kotlin library is no longer usable in kotlinc 1.3. However, it should be usable in
+ * kotlinc 1.5.
+ */
+@RunWith(Parameterized.class)
+public class MetadataFirstToLatestTest extends KotlinMetadataTestBase {
+
+  private final String EXPECTED = StringUtils.lines("foo");
+  private static final String PKG_LIB = PKG + ".crossinline_anon_lib";
+  private static final String PKG_APP = PKG + ".crossinline_anon_app";
+  private final TestParameters parameters;
+
+  private static final KotlinCompileMemoizer libJars =
+      getCompileMemoizer(
+          getKotlinFileInTest(DescriptorUtils.getBinaryNameFromJavaType(PKG_LIB), "lib"));
+
+  @Parameterized.Parameters(name = "{0}, {1}")
+  public static Collection<Object[]> data() {
+    return buildParameters(
+        getTestParameters().withCfRuntimes().build(),
+        getKotlinTestParameters()
+            .withCompiler(KotlinCompilerVersion.KOTLINC_1_3_72)
+            .withAllTargetVersions()
+            .build());
+  }
+
+  public MetadataFirstToLatestTest(
+      TestParameters parameters, KotlinTestParameters kotlinParameters) {
+    super(kotlinParameters);
+    this.parameters = parameters;
+  }
+
+  @Test
+  public void smokeTest() throws Exception {
+    runTest(
+        KotlinCompilerVersion.KOTLINC_1_5_0,
+        libJars.getForConfiguration(kotlinc, targetVersion),
+        getKotlinStdlibJar(kotlinc));
+  }
+
+  @Test
+  public void testOnFirst() throws Exception {
+    Path libJar =
+        testForR8(parameters.getBackend())
+            .addProgramFiles(libJars.getForConfiguration(kotlinc, targetVersion))
+            .addClasspathFiles(getKotlinStdlibJar(kotlinc), getKotlinAnnotationJar(kotlinc))
+            .addKeepAllClassesRule()
+            .addKeepAllAttributes()
+            .compile()
+            .writeToZip();
+    Path stdLibJar =
+        testForR8(parameters.getBackend())
+            .addProgramFiles(
+                ToolHelper.getKotlinStdlibJar(kotlinc), ToolHelper.getKotlinAnnotationJar(kotlinc))
+            .addKeepAllClassesRule()
+            .addKeepAllAttributes()
+            .allowDiagnosticWarningMessages()
+            .compile()
+            .assertAllWarningMessagesMatch(
+                equalTo("Resource 'META-INF/MANIFEST.MF' already exists."))
+            .writeToZip();
+    // TODO(b/187781614): This is expected to fail when upgrading.
+    runTest(KotlinCompilerVersion.KOTLINC_1_3_72, libJar, stdLibJar);
+  }
+
+  @Test
+  public void testOnLatest() throws Exception {
+    Path libJar =
+        testForR8(parameters.getBackend())
+            .addProgramFiles(libJars.getForConfiguration(kotlinc, targetVersion))
+            .addClasspathFiles(getKotlinStdlibJar(kotlinc), getKotlinAnnotationJar(kotlinc))
+            .addKeepAllClassesRule()
+            .addKeepAllAttributes()
+            .compile()
+            .writeToZip();
+    Path stdLibJar =
+        testForR8(parameters.getBackend())
+            .addProgramFiles(
+                ToolHelper.getKotlinStdlibJar(kotlinc), ToolHelper.getKotlinAnnotationJar(kotlinc))
+            .addKeepAllClassesRule()
+            .addKeepAllAttributes()
+            .allowDiagnosticWarningMessages()
+            .compile()
+            .assertAllWarningMessagesMatch(
+                equalTo("Resource 'META-INF/MANIFEST.MF' already exists."))
+            .writeToZip();
+    runTest(KotlinCompilerVersion.KOTLINC_1_5_0, libJar, stdLibJar);
+  }
+
+  private void runTest(KotlinCompilerVersion kotlinCompilerVersion, Path libJar, Path stdLibJar)
+      throws Exception {
+    Path output =
+        kotlinc(
+                parameters.getRuntime().asCf(),
+                new KotlinCompiler(kotlinCompilerVersion),
+                targetVersion)
+            .addClasspathFiles(libJar, stdLibJar)
+            .addSourceFiles(
+                getKotlinFileInTest(DescriptorUtils.getBinaryNameFromJavaType(PKG_APP), "main"))
+            .setOutputPath(temp.newFolder().toPath())
+            .noStdLib()
+            .compile();
+    testForJvm()
+        .addRunClasspathFiles(stdLibJar, libJar)
+        .addClasspath(output)
+        .run(parameters.getRuntime(), PKG_APP + ".MainKt")
+        .assertSuccessWithOutput(EXPECTED);
+  }
+}