diff --git a/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/JibPluginConfiguration.java b/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/JibPluginConfiguration.java
index b3ad9a5b6c..4164919e42 100644
--- a/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/JibPluginConfiguration.java
+++ b/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/JibPluginConfiguration.java
@@ -99,7 +99,7 @@ public ToAuthConfiguration() {
     }
   }
 
-  /** Used to configure {@code extraDirectory.permissions} parameter. */
+  /** Used to configure {@code extraDirectories.permissions} parameter. */
   public static class PermissionConfiguration {
 
     @Nullable @Parameter private String file;
@@ -183,35 +183,44 @@ public static class ContainerParameters {
     @Nullable @Parameter private String workingDirectory;
   }
 
+  /** Configuration for the {@code extraDirectories} parameter. */
+  public static class ExtraDirectoriesParameters {
+
+    @Parameter private List<File> paths = Collections.emptyList();
+
+    @Parameter private List<PermissionConfiguration> permissions = Collections.emptyList();
+
+    public List<File> getPaths() {
+      return paths;
+    }
+  }
+
   /** Configuration for the {@code extraDirectory} parameter. */
+  @Deprecated
   public static class ExtraDirectoryParameters {
 
     // retained for backward-compatibility for <extraDirectory><path>...<path></extraDirectory>
     @Deprecated @Nullable @Parameter private File path;
 
-    @Parameter private List<File> paths = Collections.emptyList();
-
-    @Parameter private List<PermissionConfiguration> permissions = Collections.emptyList();
+    @Deprecated @Parameter
+    private List<PermissionConfiguration> permissions = Collections.emptyList();
 
-    /**
-     * Allows users to configure {@code path} using just {@code <extraDirectory>} instead of {@code
-     * <extraDirectory><path>}.
-     *
-     * @param path the value to set {@code path} to
-     */
+    // Allows users to configure a single path using just <extraDirectory> instead of
+    // <extraDirectory><path>.
     @Deprecated
     public void set(File path) {
-      this.paths = Collections.singletonList(path);
+      this.path = path;
     }
 
+    @Deprecated
     public List<File> getPaths() {
-      return path != null ? Collections.singletonList(path) : paths;
+      return path == null ? Collections.emptyList() : Collections.singletonList(path);
     }
   }
 
   @Nullable
   @Parameter(defaultValue = "${session}", readonly = true)
-  MavenSession session;
+  private MavenSession session;
 
   @Nullable
   @Parameter(defaultValue = "${project}", readonly = true)
@@ -224,7 +233,11 @@ public List<File> getPaths() {
   @Parameter private ContainerParameters container = new ContainerParameters();
 
   // this parameter is cloned in FilesMojo
-  @Parameter private ExtraDirectoryParameters extraDirectory = new ExtraDirectoryParameters();
+  @Deprecated @Parameter
+  private ExtraDirectoryParameters extraDirectory = new ExtraDirectoryParameters();
+
+  // this parameter is cloned in FilesMojo
+  @Parameter private ExtraDirectoriesParameters extraDirectories = new ExtraDirectoriesParameters();
 
   @Parameter(
       defaultValue = "false",
@@ -512,12 +525,38 @@ String getFormat() {
    */
   List<Path> getExtraDirectories() {
     // TODO: Should inform user about nonexistent directory if using custom directory.
-    String property = getProperty(PropertyNames.EXTRA_DIRECTORY_PATH);
+    String deprecatedProperty = getProperty(PropertyNames.EXTRA_DIRECTORY_PATH);
+    String newProperty = getProperty(PropertyNames.EXTRA_DIRECTORIES_PATHS);
+
+    List<File> deprecatedPaths = extraDirectory.getPaths();
+    List<File> newPaths = extraDirectories.getPaths();
+
+    if (deprecatedProperty != null) {
+      getLog()
+          .warn(
+              "The property 'jib.extraDirectory.path' is deprecated; "
+                  + "use 'jib.extraDirectories.paths' instead");
+    }
+    if (!deprecatedPaths.isEmpty()) {
+      getLog().warn("<extraDirectory> is deprecated; use <extraDirectories> with <paths><path>");
+    }
+    if (deprecatedProperty != null && newProperty != null) {
+      throw new IllegalArgumentException(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'");
+    }
+    if (!deprecatedPaths.isEmpty() && !newPaths.isEmpty()) {
+      throw new IllegalArgumentException(
+          "You cannot configure both <extraDirectory> and <extraDirectories>");
+    }
+
+    String property = newProperty != null ? newProperty : deprecatedProperty;
     if (property != null) {
       List<String> paths = ConfigurationPropertyValidator.parseListProperty(property);
       return paths.stream().map(Paths::get).collect(Collectors.toList());
     }
-    return extraDirectory.getPaths().stream().map(File::toPath).collect(Collectors.toList());
+
+    List<File> paths = !newPaths.isEmpty() ? newPaths : deprecatedPaths;
+    return paths.stream().map(File::toPath).collect(Collectors.toList());
   }
 
   /**
@@ -526,7 +565,29 @@ List<Path> getExtraDirectories() {
    * @return the configured extra layer file permissions
    */
   List<PermissionConfiguration> getExtraDirectoryPermissions() {
-    String property = getProperty(PropertyNames.EXTRA_DIRECTORY_PERMISSIONS);
+    String deprecatedProperty = getProperty(PropertyNames.EXTRA_DIRECTORY_PERMISSIONS);
+    String newProperty = getProperty(PropertyNames.EXTRA_DIRECTORIES_PERMISSIONS);
+
+    List<PermissionConfiguration> deprecatedPermissions = extraDirectory.permissions;
+    List<PermissionConfiguration> newPermissions = extraDirectories.permissions;
+
+    if (deprecatedProperty != null) {
+      getLog()
+          .warn(
+              "The property 'jib.extraDirectory.permissions' is deprecated; "
+                  + "use 'jib.extraDirectories.permissions' instead");
+    }
+    if (deprecatedProperty != null && newProperty != null) {
+      throw new IllegalArgumentException(
+          "You cannot configure both 'jib.extraDirectory.permissions' and "
+              + "'jib.extraDirectories.permissions'");
+    }
+    if (!deprecatedPermissions.isEmpty() && !newPermissions.isEmpty()) {
+      throw new IllegalArgumentException(
+          "You cannot configure both <extraDirectory> and <extraDirectories>");
+    }
+
+    String property = newProperty != null ? newProperty : deprecatedProperty;
     if (property != null) {
       return ConfigurationPropertyValidator.parseMapProperty(property)
           .entrySet()
@@ -534,7 +595,10 @@ List<PermissionConfiguration> getExtraDirectoryPermissions() {
           .map(entry -> new PermissionConfiguration(entry.getKey(), entry.getValue()))
           .collect(Collectors.toList());
     }
-    return extraDirectory.permissions;
+
+    return !extraDirectories.getPaths().isEmpty()
+        ? extraDirectories.permissions
+        : extraDirectory.permissions;
   }
 
   boolean getAllowInsecureRegistries() {
@@ -554,6 +618,11 @@ void setProject(MavenProject project) {
     this.project = project;
   }
 
+  @VisibleForTesting
+  void setSession(MavenSession session) {
+    this.session = session;
+  }
+
   @Nullable
   String getProperty(String propertyName) {
     return MavenProjectProperties.getProperty(propertyName, project, session);
diff --git a/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojo.java b/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojo.java
index 3e5a2f6b0e..4c77e6698e 100644
--- a/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojo.java
+++ b/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojo.java
@@ -16,8 +16,11 @@
 
 package com.google.cloud.tools.jib.maven.skaffold;
 
+import com.google.cloud.tools.jib.maven.JibPluginConfiguration.ExtraDirectoriesParameters;
 import com.google.cloud.tools.jib.maven.JibPluginConfiguration.ExtraDirectoryParameters;
 import com.google.cloud.tools.jib.maven.MavenProjectProperties;
+import com.google.cloud.tools.jib.plugins.common.ConfigurationPropertyValidator;
+import com.google.cloud.tools.jib.plugins.common.PropertyNames;
 import com.google.common.annotations.VisibleForTesting;
 import com.google.common.base.Preconditions;
 import com.google.common.collect.ImmutableSet;
@@ -44,6 +47,7 @@
 import org.apache.maven.project.DependencyResolutionResult;
 import org.apache.maven.project.MavenProject;
 import org.apache.maven.project.ProjectDependenciesResolver;
+import org.eclipse.aether.graph.Dependency;
 import org.eclipse.aether.graph.DependencyFilter;
 
 /**
@@ -78,7 +82,11 @@ public class FilesMojo extends AbstractMojo {
   @Nullable @Component private ProjectDependenciesResolver projectDependenciesResolver;
 
   // This parameter is cloned from JibPluginConfiguration
-  @Parameter private ExtraDirectoryParameters extraDirectory = new ExtraDirectoryParameters();
+  @Deprecated @Parameter
+  private ExtraDirectoryParameters extraDirectory = new ExtraDirectoryParameters();
+
+  // This parameter is cloned from JibPluginConfiguration
+  @Parameter private ExtraDirectoriesParameters extraDirectories = new ExtraDirectoriesParameters();
 
   @Override
   public void execute() throws MojoExecutionException, MojoFailureException {
@@ -143,7 +151,7 @@ public void execute() throws MojoExecutionException, MojoFailureException {
       resolutionResult
           .getDependencies()
           .stream()
-          .map(org.eclipse.aether.graph.Dependency::getArtifact)
+          .map(Dependency::getArtifact)
           .filter(org.eclipse.aether.artifact.Artifact::isSnapshot)
           .map(org.eclipse.aether.artifact.Artifact::getFile)
           .forEach(System.out::println);
@@ -153,8 +161,32 @@ public void execute() throws MojoExecutionException, MojoFailureException {
     }
   }
 
-  private List<Path> resolveExtraDirectories() {
-    List<File> paths = extraDirectory.getPaths();
+  private List<Path> resolveExtraDirectories() throws MojoExecutionException {
+    // TODO: Should inform user about nonexistent directory if using custom directory.
+    String deprecatedProperty =
+        MavenProjectProperties.getProperty(PropertyNames.EXTRA_DIRECTORY_PATH, project, session);
+    String newProperty =
+        MavenProjectProperties.getProperty(PropertyNames.EXTRA_DIRECTORIES_PATHS, project, session);
+
+    List<File> deprecatedPaths = extraDirectory.getPaths();
+    List<File> newPaths = extraDirectories.getPaths();
+
+    if (deprecatedProperty != null && newProperty != null) {
+      throw new MojoExecutionException(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'");
+    }
+    if (!deprecatedPaths.isEmpty() && !newPaths.isEmpty()) {
+      throw new MojoExecutionException(
+          "You cannot configure both <extraDirectory> and <extraDirectories>");
+    }
+
+    String property = newProperty != null ? newProperty : deprecatedProperty;
+    if (property != null) {
+      List<String> paths = ConfigurationPropertyValidator.parseListProperty(property);
+      return paths.stream().map(Paths::get).map(Path::toAbsolutePath).collect(Collectors.toList());
+    }
+
+    List<File> paths = !newPaths.isEmpty() ? newPaths : deprecatedPaths;
     if (paths.isEmpty()) {
       Path projectBase =
           Preconditions.checkNotNull(project).getBasedir().getAbsoluteFile().toPath();
diff --git a/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2.java b/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2.java
index a73e74ca5a..656cf96551 100644
--- a/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2.java
+++ b/jib-maven-plugin/src/main/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2.java
@@ -17,6 +17,7 @@
 package com.google.cloud.tools.jib.maven.skaffold;
 
 import com.google.cloud.tools.jib.maven.MavenProjectProperties;
+import com.google.cloud.tools.jib.plugins.common.ConfigurationPropertyValidator;
 import com.google.cloud.tools.jib.plugins.common.PropertyNames;
 import com.google.cloud.tools.jib.plugins.common.SkaffoldFilesOutput;
 import com.google.common.annotations.VisibleForTesting;
@@ -167,12 +168,22 @@ public void execute() throws MojoExecutionException, MojoFailureException {
     }
   }
 
-  private List<Path> resolveExtraDirectories(MavenProject project) {
+  private List<Path> resolveExtraDirectories(MavenProject project) throws MojoExecutionException {
     // Try getting extra directory from project/session properties
-    String extraDirectoryProperty =
+    String deprecatedProperty =
         MavenProjectProperties.getProperty(PropertyNames.EXTRA_DIRECTORY_PATH, project, session);
-    if (extraDirectoryProperty != null) {
-      return Collections.singletonList(Paths.get(extraDirectoryProperty));
+    String newProperty =
+        MavenProjectProperties.getProperty(PropertyNames.EXTRA_DIRECTORIES_PATHS, project, session);
+
+    if (deprecatedProperty != null && newProperty != null) {
+      throw new MojoExecutionException(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'");
+    }
+
+    String property = newProperty != null ? newProperty : deprecatedProperty;
+    if (property != null) {
+      List<String> paths = ConfigurationPropertyValidator.parseListProperty(property);
+      return paths.stream().map(Paths::get).collect(Collectors.toList());
     }
 
     // Try getting extra directory from project pom
@@ -180,21 +191,31 @@ private List<Path> resolveExtraDirectories(MavenProject project) {
     if (jibMavenPlugin != null) {
       Xpp3Dom pluginConfiguration = (Xpp3Dom) jibMavenPlugin.getConfiguration();
       if (pluginConfiguration != null) {
+
         Xpp3Dom extraDirectoryConfiguration = pluginConfiguration.getChild("extraDirectory");
-        if (extraDirectoryConfiguration != null) {
-          Xpp3Dom pathChild = extraDirectoryConfiguration.getChild("path");
-          if (pathChild != null) {
-            // <extraDirectory><path>...</path></extraDirectory>
-            return Collections.singletonList(Paths.get(pathChild.getValue()));
-          }
-          Xpp3Dom pathsChild = extraDirectoryConfiguration.getChild("paths");
-          if (pathsChild != null) {
-            // <extraDirectory><paths><path>...<path><path>...<path></paths></extraDirectory>
-            return Arrays.stream(pathsChild.getChildren())
+        Xpp3Dom extraDirectoriesConfiguration = pluginConfiguration.getChild("extraDirectories");
+        if (extraDirectoryConfiguration != null && extraDirectoriesConfiguration != null) {
+          throw new MojoExecutionException(
+              "You cannot configure both <extraDirectory> and <extraDirectories>");
+        }
+
+        if (extraDirectoriesConfiguration != null) {
+          Xpp3Dom child = extraDirectoriesConfiguration.getChild("paths");
+          if (child != null) {
+            // <extraDirectories><paths><path>...</path><path>...</path></paths></extraDirectories>
+            return Arrays.stream(child.getChildren())
                 .map(Xpp3Dom::getValue)
                 .map(Paths::get)
                 .collect(Collectors.toList());
           }
+        }
+
+        if (extraDirectoryConfiguration != null) {
+          Xpp3Dom child = extraDirectoryConfiguration.getChild("path");
+          if (child != null) {
+            // <extraDirectory><path>...</path></extraDirectory>
+            return Collections.singletonList(Paths.get(child.getValue()));
+          }
           // <extraDirectory>...</extraDirectory>
           String value = extraDirectoryConfiguration.getValue();
           if (value != null) {
diff --git a/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/BuildImageMojoIntegrationTest.java b/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/BuildImageMojoIntegrationTest.java
index 69ec8cb8a3..e5218f5504 100644
--- a/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/BuildImageMojoIntegrationTest.java
+++ b/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/BuildImageMojoIntegrationTest.java
@@ -98,13 +98,9 @@ private static boolean isJava11RuntimeOrHigher() {
     return Integer.valueOf(split.iterator().next()) >= 11;
   }
 
-  /**
-   * Builds and runs jib:build on a project at {@code projectRoot} pushing to {@code
-   * imageReference}.
-   */
-  private static String buildAndRun(
-      Path projectRoot, String imageReference, String pomXml, boolean runTwice)
-      throws VerificationException, IOException, InterruptedException, DigestException {
+  private static Verifier build(
+      Path projectRoot, String imageReference, String pomXml, boolean buildTwice)
+      throws VerificationException, IOException {
     Verifier verifier = new Verifier(projectRoot.toString());
     verifier.setSystemProperty("jib.useOnlyProjectCache", "true");
     verifier.setSystemProperty("_TARGET_IMAGE", imageReference);
@@ -117,7 +113,7 @@ private static String buildAndRun(
     verifier.executeGoal("jib:build");
     float timeOne = getBuildTimeFromVerifierLog(verifier);
 
-    if (runTwice) {
+    if (buildTwice) {
       verifier.resetStreams();
       verifier.executeGoal("jib:build");
       float timeTwo = getBuildTimeFromVerifierLog(verifier);
@@ -126,7 +122,17 @@ private static String buildAndRun(
       Assert.assertTrue(String.format(failMessage, timeOne, timeTwo), timeOne > timeTwo);
     }
 
-    verifier.verifyErrorFreeLog();
+    return verifier;
+  }
+
+  /**
+   * Builds with {@code jib:build} on a project at {@code projectRoot} pushing to {@code
+   * imageReference} and run the image after pulling it.
+   */
+  private static String buildAndRun(
+      Path projectRoot, String imageReference, String pomXml, boolean buildTwice)
+      throws VerificationException, IOException, InterruptedException, DigestException {
+    build(projectRoot, imageReference, pomXml, buildTwice).verifyErrorFreeLog();
 
     String output = pullAndRunBuiltImage(imageReference);
 
@@ -417,6 +423,29 @@ public void testExecute_multipleExtraDirectories()
     assertLayerSizer(9, targetImage); // one more than usual
   }
 
+  @Test
+  public void testExecute_bothDeprecatedAndNewExtraDirectoryConfigUsed() throws IOException {
+    try {
+      build(
+          simpleTestProject.getProjectRoot(), "foo", "pom-deprecated-and-new-extra-dir.xml", false);
+      Assert.fail();
+    } catch (VerificationException ex) {
+      Assert.assertThat(
+          ex.getMessage(),
+          CoreMatchers.containsString(
+              "You cannot configure both <extraDirectory> and <extraDirectories>"));
+    }
+  }
+
+  @Test
+  public void testExecute_deprecatedExtraDirectoryConfigUsed()
+      throws IOException, VerificationException {
+    String targetImage = getGcrImageReference("simpleimage:maven");
+    build(simpleTestProject.getProjectRoot(), targetImage, "pom-deprecated-extra-dir.xml", false)
+        .verifyTextInLog(
+            "<extraDirectory> is deprecated; use <extraDirectories> with <paths><path>");
+  }
+
   @Test
   public void testExecute_defaultTarget() throws IOException {
     // Test error when 'to' is missing
diff --git a/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/JibPluginConfigurationTest.java b/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/JibPluginConfigurationTest.java
index 4a96dff604..457f4e9790 100644
--- a/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/JibPluginConfigurationTest.java
+++ b/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/JibPluginConfigurationTest.java
@@ -25,6 +25,7 @@
 import java.util.List;
 import java.util.Properties;
 import org.apache.maven.execution.MavenSession;
+import org.apache.maven.plugin.logging.Log;
 import org.apache.maven.project.MavenProject;
 import org.junit.Assert;
 import org.junit.Before;
@@ -41,6 +42,7 @@ public class JibPluginConfigurationTest {
   private final MavenProject project = new MavenProject();
   private final Properties sessionProperties = new Properties();
   @Mock private MavenSession session;
+  @Mock private Log log;
   private JibPluginConfiguration testPluginConfiguration;
 
   @Before
@@ -50,9 +52,14 @@ public void setup() {
         new JibPluginConfiguration() {
           @Override
           public void execute() {}
+
+          @Override
+          public Log getLog() {
+            return log;
+          }
         };
     testPluginConfiguration.setProject(project);
-    testPluginConfiguration.session = session;
+    testPluginConfiguration.setSession(session);
   }
 
   @Test
@@ -111,10 +118,10 @@ public void testSystemProperties() {
     sessionProperties.put("jib.container.workingDirectory", "working directory");
     Assert.assertEquals("working directory", testPluginConfiguration.getWorkingDirectory());
 
-    sessionProperties.put("jib.extraDirectory.path", "custom-jib");
+    sessionProperties.put("jib.extraDirectories.paths", "custom-jib");
     Assert.assertEquals(
         Arrays.asList(Paths.get("custom-jib")), testPluginConfiguration.getExtraDirectories());
-    sessionProperties.put("jib.extraDirectory.permissions", "/test/file1=123,/another/file=456");
+    sessionProperties.put("jib.extraDirectories.permissions", "/test/file1=123,/another/file=456");
     List<PermissionConfiguration> permissions =
         testPluginConfiguration.getExtraDirectoryPermissions();
     Assert.assertEquals("/test/file1", permissions.get(0).getFile().get());
@@ -173,12 +180,12 @@ public void testPomProperties() {
     project.getProperties().setProperty("jib.container.workingDirectory", "working directory");
     Assert.assertEquals("working directory", testPluginConfiguration.getWorkingDirectory());
 
-    project.getProperties().setProperty("jib.extraDirectory.path", "custom-jib");
+    project.getProperties().setProperty("jib.extraDirectories.paths", "custom-jib");
     Assert.assertEquals(
         Arrays.asList(Paths.get("custom-jib")), testPluginConfiguration.getExtraDirectories());
     project
         .getProperties()
-        .setProperty("jib.extraDirectory.permissions", "/test/file1=123,/another/file=456");
+        .setProperty("jib.extraDirectories.permissions", "/test/file1=123,/another/file=456");
     List<PermissionConfiguration> permissions =
         testPluginConfiguration.getExtraDirectoryPermissions();
     Assert.assertEquals("/test/file1", permissions.get(0).getFile().get());
@@ -200,4 +207,110 @@ public void testEmptyOrNullTags() {
       Assert.assertEquals("jib.to.tags has empty tag", ex.getMessage());
     }
   }
+
+  @Test
+  public void testDeprecatedSystemProperties() {
+    sessionProperties.put("jib.extraDirectory.path", "custom-jib");
+    Assert.assertEquals(
+        Arrays.asList(Paths.get("custom-jib")), testPluginConfiguration.getExtraDirectories());
+    sessionProperties.put("jib.extraDirectory.permissions", "/test/file13=650,/another/file24=777");
+    List<PermissionConfiguration> permissions =
+        testPluginConfiguration.getExtraDirectoryPermissions();
+    Assert.assertEquals("/test/file13", permissions.get(0).getFile().get());
+    Assert.assertEquals("650", permissions.get(0).getMode().get());
+    Assert.assertEquals("/another/file24", permissions.get(1).getFile().get());
+    Assert.assertEquals("777", permissions.get(1).getMode().get());
+
+    Mockito.verify(log, Mockito.times(1))
+        .warn(
+            "The property 'jib.extraDirectory.path' is deprecated; "
+                + "use 'jib.extraDirectories.paths' instead");
+  }
+
+  @Test
+  public void testDeprecatedProperties() {
+    Properties projectProperties = project.getProperties();
+
+    projectProperties.setProperty("jib.extraDirectory.path", "this-is-extra");
+    Assert.assertEquals(
+        Arrays.asList(Paths.get("this-is-extra")), testPluginConfiguration.getExtraDirectories());
+
+    projectProperties.setProperty(
+        "jib.extraDirectory.permissions", "/test/file1=654,/dir/file2=321");
+    List<PermissionConfiguration> permissions =
+        testPluginConfiguration.getExtraDirectoryPermissions();
+    Assert.assertEquals("/test/file1", permissions.get(0).getFile().get());
+    Assert.assertEquals("654", permissions.get(0).getMode().get());
+    Assert.assertEquals("/dir/file2", permissions.get(1).getFile().get());
+    Assert.assertEquals("321", permissions.get(1).getMode().get());
+
+    Mockito.verify(log, Mockito.times(1))
+        .warn(
+            "The property 'jib.extraDirectory.path' is deprecated; "
+                + "use 'jib.extraDirectories.paths' instead");
+  }
+
+  @Test
+  public void testGetExtraDirectories_bothSystemPropertiesUsed() {
+    sessionProperties.put("jib.extraDirectory.path", "deprecated-property");
+    sessionProperties.put("jib.extraDirectories.paths", "new-property");
+
+    try {
+      testPluginConfiguration.getExtraDirectories();
+      Assert.fail();
+    } catch (IllegalArgumentException ex) {
+      Assert.assertEquals(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'",
+          ex.getMessage());
+    }
+  }
+
+  @Test
+  public void testGetExtraDirectories_bothPropertiesUsed() {
+    Properties projectProperties = project.getProperties();
+    projectProperties.setProperty("jib.extraDirectory.path", "deprecated-property");
+    projectProperties.setProperty("jib.extraDirectories.paths", "new-property");
+
+    try {
+      testPluginConfiguration.getExtraDirectories();
+      Assert.fail();
+    } catch (IllegalArgumentException ex) {
+      Assert.assertEquals(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'",
+          ex.getMessage());
+    }
+  }
+
+  @Test
+  public void testGetExtraDirectoryPermissions_bothSystemPropertiesUsed() {
+    sessionProperties.put("jib.extraDirectory.permissions", "deprecated-property");
+    sessionProperties.put("jib.extraDirectories.permissions", "new-property");
+
+    try {
+      testPluginConfiguration.getExtraDirectoryPermissions();
+      Assert.fail();
+    } catch (IllegalArgumentException ex) {
+      Assert.assertEquals(
+          "You cannot configure both 'jib.extraDirectory.permissions' and "
+              + "'jib.extraDirectories.permissions'",
+          ex.getMessage());
+    }
+  }
+
+  @Test
+  public void testGetExtraDirectoryPermissions_bothPropertiesUsed() {
+    Properties projectProperties = project.getProperties();
+    projectProperties.setProperty("jib.extraDirectory.permissions", "deprecated-property");
+    projectProperties.setProperty("jib.extraDirectories.permissions", "new-property");
+
+    try {
+      testPluginConfiguration.getExtraDirectoryPermissions();
+      Assert.fail();
+    } catch (IllegalArgumentException ex) {
+      Assert.assertEquals(
+          "You cannot configure both 'jib.extraDirectory.permissions' and "
+              + "'jib.extraDirectories.permissions'",
+          ex.getMessage());
+    }
+  }
 }
diff --git a/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2Test.java b/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2Test.java
index 4571bf6506..1941e3b31b 100644
--- a/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2Test.java
+++ b/jib-maven-plugin/src/test/java/com/google/cloud/tools/jib/maven/skaffold/FilesMojoV2Test.java
@@ -49,6 +49,7 @@ private static void verifyFiles(
       Path projectRoot,
       String pomXml,
       String module,
+      List<String> extraCliOptions,
       List<String> buildFiles,
       List<String> inputFiles)
       throws VerificationException, IOException {
@@ -62,6 +63,7 @@ private static void verifyFiles(
       verifier.addCliOption(module);
       verifier.addCliOption("-am");
     }
+    extraCliOptions.forEach(verifier::addCliOption);
     verifier.executeGoal("jib:" + FilesMojoV2.GOAL_NAME);
 
     verifier.verifyErrorFreeLog();
@@ -84,6 +86,7 @@ public void testFilesMojo_singleModule() throws VerificationException, IOExcepti
         projectRoot,
         "pom.xml",
         null,
+        Collections.emptyList(),
         Collections.singletonList(projectRoot.resolve("pom.xml").toString()),
         Arrays.asList(
             projectRoot.resolve("src/main/java").toString(),
@@ -100,6 +103,7 @@ public void testFilesMojo_singleModuleWithMultipleExtraDirectories()
         projectRoot,
         "pom-extra-dirs.xml",
         null,
+        Collections.emptyList(),
         Collections.singletonList(projectRoot.resolve("pom-extra-dirs.xml").toString()),
         Arrays.asList(
             projectRoot.resolve("src/main/java").toString(),
@@ -117,6 +121,7 @@ public void testFilesMojo_multiModuleSimpleService() throws VerificationExceptio
         projectRoot,
         "pom.xml",
         "simple-service",
+        Collections.emptyList(),
         Arrays.asList(
             projectRoot.resolve("pom.xml").toString(),
             simpleServiceRoot.resolve("pom.xml").toString()),
@@ -136,6 +141,7 @@ public void testFilesMojo_multiModuleComplexService() throws VerificationExcepti
         projectRoot,
         "pom.xml",
         "complex-service",
+        Collections.emptyList(),
         Arrays.asList(
             projectRoot.resolve("pom.xml").toString(),
             libRoot.resolve("pom.xml").toString(),
@@ -153,4 +159,21 @@ public void testFilesMojo_multiModuleComplexService() throws VerificationExcepti
                     ".m2/repository/com/google/guava/guava/HEAD-jre-SNAPSHOT/guava-HEAD-jre-SNAPSHOT.jar")
                 .toString()));
   }
+
+  @Test
+  public void testFilesMojo_extraDirectoriesProperty() throws VerificationException, IOException {
+    Path projectRoot = simpleTestProject.getProjectRoot();
+
+    verifyFiles(
+        projectRoot,
+        "pom.xml",
+        null,
+        Arrays.asList("-Djib.extraDirectories.paths=/some/extra/dir,/another/extra/dir"),
+        Collections.singletonList(projectRoot.resolve("pom.xml").toString()),
+        Arrays.asList(
+            projectRoot.resolve("src/main/java").toString(),
+            projectRoot.resolve("src/main/resources").toString(),
+            Paths.get("/some/extra/dir").toString(),
+            Paths.get("/another/extra/dir").toString()));
+  }
 }
diff --git a/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-deprecated-and-new-extra-dir.xml b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-deprecated-and-new-extra-dir.xml
new file mode 100644
index 0000000000..19f2919955
--- /dev/null
+++ b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-deprecated-and-new-extra-dir.xml
@@ -0,0 +1,52 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<project xmlns="http://maven.apache.org/POM/4.0.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
+    xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 http://maven.apache.org/xsd/maven-4.0.0.xsd">
+  <modelVersion>4.0.0</modelVersion>
+
+  <groupId>com.test</groupId>
+  <artifactId>my-artifact-id</artifactId>
+  <version>1</version>
+
+  <properties>
+    <project.build.sourceEncoding>UTF-8</project.build.sourceEncoding>
+    <project.reporting.outputEncoding>UTF-8</project.reporting.outputEncoding>
+    <jib-maven-plugin.version>@@PluginVersion@@</jib-maven-plugin.version>
+    <jib.to.image>${_TARGET_IMAGE}</jib.to.image>
+    <jib.container.args>An argument.</jib.container.args>
+    <jib.container.ports>1000/tcp,2000-2003/udp</jib.container.ports>
+    <jib.container.labels>key1=value1,key2=value2</jib.container.labels>
+  </properties>
+
+  <dependencies>
+    <dependency>
+      <groupId>com.test</groupId>
+      <artifactId>dependency</artifactId>
+      <version>1.0.0</version>
+      <scope>system</scope>
+      <systemPath>${project.basedir}/libs/dependency-1.0.0.jar</systemPath>
+    </dependency>
+  </dependencies>
+
+  <build>
+    <plugins>
+      <plugin>
+        <groupId>org.apache.maven.plugins</groupId>
+        <artifactId>maven-compiler-plugin</artifactId>
+        <configuration>
+          <source>1.8</source>
+          <target>1.8</target>
+        </configuration>
+      </plugin>
+
+      <plugin>
+        <groupId>com.google.cloud.tools</groupId>
+        <artifactId>jib-maven-plugin</artifactId>
+        <version>${jib-maven-plugin.version}</version>
+        <configuration>
+          <extraDirectory>deprecated-config</extraDirectory>
+          <extraDirectories><paths><path>good-config</path></paths></extraDirectories>
+        </configuration>
+      </plugin>
+    </plugins>
+  </build>
+</project>
diff --git a/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-deprecated-extra-dir.xml b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-deprecated-extra-dir.xml
new file mode 100644
index 0000000000..ec9beeaa69
--- /dev/null
+++ b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-deprecated-extra-dir.xml
@@ -0,0 +1,51 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<project xmlns="http://maven.apache.org/POM/4.0.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
+    xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 http://maven.apache.org/xsd/maven-4.0.0.xsd">
+  <modelVersion>4.0.0</modelVersion>
+
+  <groupId>com.test</groupId>
+  <artifactId>my-artifact-id</artifactId>
+  <version>1</version>
+
+  <properties>
+    <project.build.sourceEncoding>UTF-8</project.build.sourceEncoding>
+    <project.reporting.outputEncoding>UTF-8</project.reporting.outputEncoding>
+    <jib-maven-plugin.version>@@PluginVersion@@</jib-maven-plugin.version>
+    <jib.to.image>${_TARGET_IMAGE}</jib.to.image>
+    <jib.container.args>An argument.</jib.container.args>
+    <jib.container.ports>1000/tcp,2000-2003/udp</jib.container.ports>
+    <jib.container.labels>key1=value1,key2=value2</jib.container.labels>
+  </properties>
+
+  <dependencies>
+    <dependency>
+      <groupId>com.test</groupId>
+      <artifactId>dependency</artifactId>
+      <version>1.0.0</version>
+      <scope>system</scope>
+      <systemPath>${project.basedir}/libs/dependency-1.0.0.jar</systemPath>
+    </dependency>
+  </dependencies>
+
+  <build>
+    <plugins>
+      <plugin>
+        <groupId>org.apache.maven.plugins</groupId>
+        <artifactId>maven-compiler-plugin</artifactId>
+        <configuration>
+          <source>1.8</source>
+          <target>1.8</target>
+        </configuration>
+      </plugin>
+
+      <plugin>
+        <groupId>com.google.cloud.tools</groupId>
+        <artifactId>jib-maven-plugin</artifactId>
+        <version>${jib-maven-plugin.version}</version>
+        <configuration>
+          <extraDirectory>deprecated-config</extraDirectory>
+        </configuration>
+      </plugin>
+    </plugins>
+  </build>
+</project>
diff --git a/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-extra-dirs.xml b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-extra-dirs.xml
index 3e3f399c62..1c594f7d8f 100644
--- a/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-extra-dirs.xml
+++ b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-extra-dirs.xml
@@ -43,12 +43,12 @@
         <artifactId>jib-maven-plugin</artifactId>
         <version>${jib-maven-plugin.version}</version>
         <configuration>
-          <extraDirectory>
+          <extraDirectories>
             <paths>
               <path>${project.basedir}/src/main/jib-custom</path>
               <path>${project.basedir}/src/main/jib-custom-2</path>
             </paths>
-          </extraDirectory>
+          </extraDirectories>
         </configuration>
       </plugin>
     </plugins>
diff --git a/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/ConfigurationPropertyValidator.java b/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/ConfigurationPropertyValidator.java
index c2dd0922d4..c4ee6a7c5a 100644
--- a/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/ConfigurationPropertyValidator.java
+++ b/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/ConfigurationPropertyValidator.java
@@ -23,10 +23,8 @@
 import com.google.cloud.tools.jib.image.ImageReference;
 import com.google.cloud.tools.jib.image.InvalidImageReferenceException;
 import com.google.common.base.Strings;
-import com.google.common.collect.ImmutableList;
-import com.google.common.collect.ImmutableMap;
 import java.util.ArrayList;
-import java.util.HashMap;
+import java.util.LinkedHashMap;
 import java.util.List;
 import java.util.Map;
 import java.util.Optional;
@@ -38,7 +36,7 @@
 public class ConfigurationPropertyValidator {
 
   /** Matches key-value pairs in the form of "key=value" */
-  private static final Pattern ENVIRONMENT_PATTERN = Pattern.compile("(?<name>[^=]+)=(?<value>.*)");
+  private static final Pattern KEY_VALUE_PATTERN = Pattern.compile("(?<name>[^=]+)=(?<value>.*)");
 
   /**
    * Gets a {@link Credential} from a username and password. First tries system properties, then
@@ -149,18 +147,18 @@ public static ImageReference getGeneratedTargetDockerTag(
    * @return the map of parsed values
    */
   public static Map<String, String> parseMapProperty(String property) {
-    Map<String, String> result = new HashMap<>();
+    Map<String, String> result = new LinkedHashMap<>(); // LinkedHashMap to keep insertion order
 
     // Split on non-escaped commas
     List<String> entries = parseListProperty(property);
     for (String entry : entries) {
-      Matcher matcher = ENVIRONMENT_PATTERN.matcher(entry);
+      Matcher matcher = KEY_VALUE_PATTERN.matcher(entry);
       if (!matcher.matches()) {
         throw new IllegalArgumentException("'" + entry + "' is not a valid key-value pair");
       }
       result.put(matcher.group("name"), matcher.group("value"));
     }
-    return ImmutableMap.copyOf(result);
+    return result;
   }
 
   /**
@@ -183,7 +181,7 @@ public static List<String> parseListProperty(String property) {
       }
     }
     items.add(property.substring(startIndex));
-    return ImmutableList.copyOf(items);
+    return items;
   }
 
   private ConfigurationPropertyValidator() {}
diff --git a/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/PropertyNames.java b/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/PropertyNames.java
index 5347625eb6..0e9c46326b 100644
--- a/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/PropertyNames.java
+++ b/jib-plugins-common/src/main/java/com/google/cloud/tools/jib/plugins/common/PropertyNames.java
@@ -46,8 +46,13 @@ public class PropertyNames {
   public static final String BASE_IMAGE_CACHE = "jib.baseImageCache";
   public static final String APPLICATION_CACHE = "jib.applicationCache";
   public static final String ALLOW_INSECURE_REGISTRIES = "jib.allowInsecureRegistries";
-  public static final String EXTRA_DIRECTORY_PATH = "jib.extraDirectory.path";
+  @Deprecated public static final String EXTRA_DIRECTORY_PATH = "jib.extraDirectory.path";
+  public static final String EXTRA_DIRECTORIES_PATHS = "jib.extraDirectories.paths";
+
+  @Deprecated
   public static final String EXTRA_DIRECTORY_PERMISSIONS = "jib.extraDirectory.permissions";
+
+  public static final String EXTRA_DIRECTORIES_PERMISSIONS = "jib.extraDirectories.permissions";
   public static final String DOCKER_CLIENT_EXECUTABLE = "jib.dockerClient.executable";
   public static final String DOCKER_CLIENT_ENVIRONMENT = "jib.dockerClient.environment";
   public static final String SKIP = "jib.skip";