diff --git a/java/flight/flight-sql-jdbc-driver/pom.xml b/java/flight/flight-sql-jdbc-driver/pom.xml
index 148319e5d9d64..a739874d3924e 100644
--- a/java/flight/flight-sql-jdbc-driver/pom.xml
+++ b/java/flight/flight-sql-jdbc-driver/pom.xml
@@ -127,14 +127,14 @@ under the License.
                   <pattern>mozilla.</pattern>
                   <shadedPattern>org.apache.arrow.driver.jdbc.shaded.mozilla.</shadedPattern>
                 </relocation>
-                <!-- Entries to relocate netty native libraries  -->
+                <!-- Entries to relocate netty native libraries. Prefix has to match relocation prefix (dots replaced with underscore)  -->
                 <relocation>
                   <pattern>META-INF.native.libnetty_</pattern>
-                  <shadedPattern>META-INF.native.liboaadj_netty_</shadedPattern>
+                  <shadedPattern>META-INF.native.liborg_apache_arrow_driver_jdbc_shaded_netty_</shadedPattern>
                 </relocation>
                 <relocation>
                   <pattern>META-INF.native.netty_</pattern>
-                  <shadedPattern>META-INF.native.oaadj_netty_</shadedPattern>
+                  <shadedPattern>META-INF.native.org_apache_arrow_driver_jdbc_shaded_netty_</shadedPattern>
                 </relocation>
               </relocations>
               <transformers>
@@ -159,8 +159,11 @@ under the License.
                     <exclude>**/*.SF</exclude>
                     <exclude>**/*.RSA</exclude>
                     <exclude>**/*.DSA</exclude>
-                    <exclude>META-INF/native/libio_grpc_netty*</exclude>
-                    <exclude>META-INF/native/io_grpc_netty_shaded*</exclude>
+                    <!-- Requires some resource transformer -->
+                    <exclude>META-INF/native-image/</exclude>
+                    <exclude>META-INF/proguard/</exclude>
+                    <!-- Requires MSHADE-406 -->
+                    <exclude>META-INF/versions/</exclude>
                     <exclude>**/*.proto</exclude>
                     <exclude>**/module-info.class</exclude>
                   </excludes>
diff --git a/java/flight/flight-sql-jdbc-driver/src/test/java/org/apache/arrow/driver/jdbc/ITDriverJarValidation.java b/java/flight/flight-sql-jdbc-driver/src/test/java/org/apache/arrow/driver/jdbc/ITDriverJarValidation.java
index b45845485a041..a0e108d6a067b 100644
--- a/java/flight/flight-sql-jdbc-driver/src/test/java/org/apache/arrow/driver/jdbc/ITDriverJarValidation.java
+++ b/java/flight/flight-sql-jdbc-driver/src/test/java/org/apache/arrow/driver/jdbc/ITDriverJarValidation.java
@@ -18,20 +18,26 @@
 
 import static org.junit.jupiter.api.Assertions.assertEquals;
 import static org.junit.jupiter.api.Assertions.assertNotNull;
-import static org.junit.jupiter.api.Assertions.fail;
 
 import com.google.common.collect.ImmutableSet;
 import java.io.File;
 import java.io.IOException;
+import java.lang.reflect.InvocationTargetException;
+import java.lang.reflect.Method;
 import java.net.JarURLConnection;
+import java.net.URISyntaxException;
 import java.net.URL;
-import java.util.Enumeration;
+import java.net.URLClassLoader;
 import java.util.Set;
 import java.util.concurrent.TimeUnit;
+import java.util.function.Predicate;
 import java.util.jar.JarEntry;
 import java.util.jar.JarFile;
+import java.util.stream.Stream;
+import org.junit.jupiter.api.Assertions;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.Timeout;
+import org.junit.jupiter.api.function.Executable;
 
 /**
  * Check the content of the JDBC driver jar
@@ -48,52 +54,92 @@ public class ITDriverJarValidation {
 
   /** List of allowed prefixes a jar entry may match. */
   public static final Set<String> ALLOWED_PREFIXES =
-      ImmutableSet.of("org/apache/arrow/driver/jdbc/", "META-INF/");
+      ImmutableSet.of(
+          "org/apache/arrow/driver/jdbc/", // Driver code
+          "META-INF/maven/", // Maven metadata (useful for security scanner
+          "META-INF/services/", // ServiceLoader implementations
+          "META-INF/license/",
+          "META-INF/licenses/",
+          // Prefixes for native libraries
+          "META-INF/native/liborg_apache_arrow_driver_jdbc_shaded_",
+          "META-INF/native/org_apache_arrow_driver_jdbc_shaded_");
 
   /** List of allowed files a jar entry may match. */
   public static final Set<String> ALLOWED_FILES =
-      ImmutableSet.of("arrow-git.properties", "properties/flight.properties");
+      ImmutableSet.of(
+          "arrow-git.properties",
+          "properties/flight.properties",
+          "META-INF/io.netty.versions.properties",
+          "META-INF/MANIFEST.MF",
+          "META-INF/DEPENDENCIES",
+          "META-INF/FastDoubleParser-LICENSE",
+          "META-INF/FastDoubleParser-NOTICE",
+          "META-INF/LICENSE",
+          "META-INF/LICENSE.txt",
+          "META-INF/NOTICE",
+          "META-INF/NOTICE.txt",
+          "META-INF/thirdparty-LICENSE",
+          "META-INF/bigint-LICENSE");
 
   // This method is designed to work with Maven failsafe plugin and expects the
   // JDBC driver jar to be present in the test classpath (instead of the individual classes)
-  private static JarFile getJdbcJarFile() throws IOException {
+  private static File getJdbcJarFile() throws IOException {
     // Check if an override has been set
     if (JDBC_DRIVER_PATH_OVERRIDE != null) {
-      return new JarFile(new File(JDBC_DRIVER_PATH_OVERRIDE));
+      return new File(JDBC_DRIVER_PATH_OVERRIDE);
     }
 
-    // Check classpath to find the driver jar
+    // Check classpath to find the driver jar (without loading the class)
     URL driverClassURL =
         ITDriverJarValidation.class
             .getClassLoader()
             .getResource("org/apache/arrow/driver/jdbc/ArrowFlightJdbcDriver.class");
 
-    assertNotNull(driverClassURL, "Driver jar was not detected in the classpath");
+    assertNotNull(driverClassURL, "Driver class was not detected in the classpath");
     assertEquals(
-        "jar", driverClassURL.getProtocol(), "Driver jar was not detected in the classpath");
+        "jar", driverClassURL.getProtocol(), "Driver class was not found inside a jar file");
 
+    // Return the enclosing jar file
     JarURLConnection connection = (JarURLConnection) driverClassURL.openConnection();
-    return connection.getJarFile();
+    try {
+      return new File(connection.getJarFileURL().toURI());
+    } catch (URISyntaxException e) {
+      throw new IOException(e);
+    }
   }
 
+  /** Validate the content of the jar to enforce all 3rd party dependencies have been shaded. */
   @Test
   @Timeout(value = 2, unit = TimeUnit.MINUTES)
   public void validateShadedJar() throws IOException {
-    // Validate the content of the jar to enforce all 3rd party dependencies have
-    // been shaded
-    try (JarFile jar = getJdbcJarFile()) {
-      for (Enumeration<JarEntry> entries = jar.entries(); entries.hasMoreElements(); ) {
-        final JarEntry entry = entries.nextElement();
-        if (entry.isDirectory()) {
-          // Directories are ignored
-          continue;
-        }
-
-        try {
-          checkEntryAllowed(entry.getName());
-        } catch (AssertionError e) {
-          fail(e.getMessage());
-        }
+
+    try (JarFile jar = new JarFile(getJdbcJarFile())) {
+      Stream<Executable> executables =
+          jar.stream()
+              .filter(Predicate.not(JarEntry::isDirectory))
+              .map(
+                  entry -> {
+                    return () -> checkEntryAllowed(entry.getName());
+                  });
+
+      Assertions.assertAll(executables);
+    }
+  }
+
+  /** Check that relocated netty code can also load matching native library. */
+  @Test
+  @Timeout(value = 2, unit = TimeUnit.MINUTES)
+  public void checkNettyOpenSslNativeLoader() throws Throwable {
+    try (URLClassLoader driverClassLoader =
+        new URLClassLoader(new URL[] {getJdbcJarFile().toURI().toURL()}, null)) {
+      Class<?> openSslClass =
+          driverClassLoader.loadClass(
+              "org.apache.arrow.driver.jdbc.shaded.io.netty.handler.ssl.OpenSsl");
+      Method method = openSslClass.getDeclaredMethod("ensureAvailability");
+      try {
+        method.invoke(null);
+      } catch (InvocationTargetException e) {
+        throw e.getCause();
       }
     }
   }