diff --git a/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/JibRunHelper.java b/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/JibRunHelper.java
index b2cb9a63ef..fa06d3f1a4 100644
--- a/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/JibRunHelper.java
+++ b/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/JibRunHelper.java
@@ -89,7 +89,7 @@ static void buildAndRunAdditionalTag(
     assertCreationTimeEpoch(additionalImageReference);
   }
 
-  static void buildToDockerDaemon(
+  static BuildResult buildToDockerDaemon(
       TestProject testProject, String imageReference, String gradleBuildFile)
       throws IOException, InterruptedException, DigestException {
     BuildResult buildResult =
@@ -106,6 +106,8 @@ static void buildToDockerDaemon(
 
     String history = new Command("docker", "history", imageReference).run();
     Assert.assertThat(history, CoreMatchers.containsString("jib-gradle-plugin"));
+
+    return buildResult;
   }
 
   static String buildToDockerDaemonAndRun(
diff --git a/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/SingleProjectIntegrationTest.java b/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/SingleProjectIntegrationTest.java
index 2dcefd38ed..7af925c53f 100644
--- a/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/SingleProjectIntegrationTest.java
+++ b/jib-gradle-plugin/src/integration-test/java/com/google/cloud/tools/jib/gradle/SingleProjectIntegrationTest.java
@@ -129,6 +129,22 @@ private static void assertDockerInspect(String imageReference)
                 + "            }"));
   }
 
+  private static void assertExtraDirectoryDeprecationWarning(String pomXml)
+      throws DigestException, IOException, InterruptedException {
+    String targetImage = "localhost:6000/simpleimage:gradle" + System.nanoTime();
+    BuildResult buildResult =
+        JibRunHelper.buildToDockerDaemon(simpleTestProject, targetImage, pomXml);
+    Assert.assertEquals(
+        "Hello, world. \nrw-r--r--\nrw-r--r--\nfoo\ncat\n",
+        new Command("docker", "run", "--rm", targetImage).run());
+    Assert.assertThat(
+        buildResult.getOutput(),
+        CoreMatchers.containsString(
+            "'jib.extraDirectory', 'jib.extraDirectory.path', and 'jib.extraDirectory.permissions' "
+                + "are deprecated; use 'jib.extraDirectories.paths' and "
+                + "'jib.extraDirectories.permissions'"));
+  }
+
   private static String buildAndRunComplex(
       String imageReference, String username, String password, LocalRegistry targetRegistry)
       throws IOException, InterruptedException {
@@ -232,6 +248,24 @@ public void testDockerDaemon_simpleWithIncompatibleJava11()
     }
   }
 
+  @Test
+  public void testDockerDaemon_simple_deprecatedExtraDirectory()
+      throws DigestException, IOException, InterruptedException {
+    assertExtraDirectoryDeprecationWarning("build-extra-dir-deprecated.gradle");
+  }
+
+  @Test
+  public void testDockerDaemon_simple_deprecatedExtraDirectory2()
+      throws DigestException, IOException, InterruptedException {
+    assertExtraDirectoryDeprecationWarning("build-extra-dir-deprecated2.gradle");
+  }
+
+  @Test
+  public void testDockerDaemon_simple_deprecatedExtraDirectory3()
+      throws DigestException, IOException, InterruptedException {
+    assertExtraDirectoryDeprecationWarning("build-extra-dir-deprecated3.gradle");
+  }
+
   @Test
   public void testDockerDaemon_simple_multipleExtraDirectories()
       throws DigestException, IOException, InterruptedException {
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated.gradle
new file mode 100644
index 0000000000..f330a8f97a
--- /dev/null
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated.gradle
@@ -0,0 +1,20 @@
+plugins {
+  id 'java'
+  id 'com.google.cloud.tools.jib'
+}
+
+sourceCompatibility = 1.8
+targetCompatibility = 1.8
+
+repositories {
+  mavenCentral()
+}
+
+dependencies {
+  compile files('libs/dependency-1.0.0.jar')
+}
+
+jib.to.image = System.getProperty("_TARGET_IMAGE")
+jib.extraDirectory {
+  path = file('src/main/custom-extra-dir')
+}
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated2.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated2.gradle
new file mode 100644
index 0000000000..4eeb3e5c56
--- /dev/null
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated2.gradle
@@ -0,0 +1,18 @@
+plugins {
+  id 'java'
+  id 'com.google.cloud.tools.jib'
+}
+
+sourceCompatibility = 1.8
+targetCompatibility = 1.8
+
+repositories {
+  mavenCentral()
+}
+
+dependencies {
+  compile files('libs/dependency-1.0.0.jar')
+}
+
+jib.to.image = System.getProperty("_TARGET_IMAGE")
+jib.extraDirectory = file('src/main/custom-extra-dir')
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated3.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated3.gradle
new file mode 100644
index 0000000000..3d0a53203f
--- /dev/null
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dir-deprecated3.gradle
@@ -0,0 +1,18 @@
+plugins {
+  id 'java'
+  id 'com.google.cloud.tools.jib'
+}
+
+sourceCompatibility = 1.8
+targetCompatibility = 1.8
+
+repositories {
+  mavenCentral()
+}
+
+dependencies {
+  compile files('libs/dependency-1.0.0.jar')
+}
+
+jib.to.image = System.getProperty("_TARGET_IMAGE")
+jib.extraDirectory.path = file('src/main/custom-extra-dir')
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs.gradle
index d185ff2603..d3a4ff06c8 100644
--- a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs.gradle
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs.gradle
@@ -15,4 +15,4 @@ dependencies {
 }
 
 jib.to.image = System.getProperty("_TARGET_IMAGE")
-jib.extraDirectory = ['src/main/custom-extra-dir', 'src/main/custom-extra-dir2']
+jib.extraDirectories.paths = ['src/main/custom-extra-dir', 'src/main/custom-extra-dir2']
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs2.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs2.gradle
index 07ebab8972..362d5b54da 100644
--- a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs2.gradle
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build-extra-dirs2.gradle
@@ -15,7 +15,7 @@ dependencies {
 }
 
 jib.to.image = System.getProperty("_TARGET_IMAGE")
-jib.extraDirectory {
-  path = files('src/main/custom-extra-dir', 'src/main/custom-extra-dir2')
+jib.extraDirectories {
+  paths = files('src/main/custom-extra-dir', 'src/main/custom-extra-dir2')
   permissions = ['/baz':'705']
 }
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build.gradle
index b350cfeb4d..84b461ad2a 100644
--- a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build.gradle
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/build.gradle
@@ -28,5 +28,5 @@ jib {
     workingDirectory = '/home'
     extraClasspath = ['/d1','/d2']
   }
-  extraDirectory = file('src/main/custom-extra-dir')
+  extraDirectories.paths = file('src/main/custom-extra-dir')
 }
diff --git a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/complex-build.gradle b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/complex-build.gradle
index 9a9b9d1fbe..de303ff081 100644
--- a/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/complex-build.gradle
+++ b/jib-gradle-plugin/src/integration-test/resources/gradle/projects/simple/complex-build.gradle
@@ -39,8 +39,8 @@ jib {
     labels = [key1:'value1', key2:'value2']
     volumes = ['/var/log', '/var/log2']
   }
-  extraDirectory {
-    path = file('src/main/custom-extra-dir')
+  extraDirectories {
+    paths = file('src/main/custom-extra-dir')
     permissions = ['/foo':'755', '/bar/cat':'777']
   }
   allowInsecureRegistries = true
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildDockerTask.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildDockerTask.java
index afc2fdb98b..9a10c72762 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildDockerTask.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildDockerTask.java
@@ -101,6 +101,7 @@ public void buildDocker()
 
     // Asserts required @Input parameters are not null.
     Preconditions.checkNotNull(jibExtension);
+    TaskCommon.checkDeprecatedUsage(jibExtension, getLogger());
     TaskCommon.disableHttpLogging();
 
     try {
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildImageTask.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildImageTask.java
index 15fe7da536..d887cfce38 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildImageTask.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildImageTask.java
@@ -78,6 +78,7 @@ public void buildImage()
           MainClassInferenceException {
     // Asserts required @Input parameters are not null.
     Preconditions.checkNotNull(jibExtension);
+    TaskCommon.checkDeprecatedUsage(jibExtension, getLogger());
     TaskCommon.disableHttpLogging();
 
     try {
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildTarTask.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildTarTask.java
index 57de55d8f5..5a5a55715d 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildTarTask.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/BuildTarTask.java
@@ -81,7 +81,7 @@ public void setTargetImage(String targetImage) {
   @InputFiles
   public FileCollection getInputFiles() {
     List<Path> extraDirectories =
-        Preconditions.checkNotNull(jibExtension).getExtraDirectory().getPaths();
+        Preconditions.checkNotNull(jibExtension).getExtraDirectories().getPaths();
     return extraDirectories
         .stream()
         .map(Path::toFile)
@@ -105,6 +105,7 @@ public void buildTar()
           MainClassInferenceException {
     // Asserts required @Input parameters are not null.
     Preconditions.checkNotNull(jibExtension);
+    TaskCommon.checkDeprecatedUsage(jibExtension, getLogger());
     TaskCommon.disableHttpLogging();
 
     try {
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/ExtraDirectoryParameters.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/ExtraDirectoriesParameters.java
similarity index 71%
rename from jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/ExtraDirectoryParameters.java
rename to jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/ExtraDirectoriesParameters.java
index 2d419becc5..219b52eb94 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/ExtraDirectoryParameters.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/ExtraDirectoriesParameters.java
@@ -30,17 +30,19 @@
 import org.gradle.api.tasks.Input;
 import org.gradle.api.tasks.Internal;
 
-/** Object in {@link JibExtension} that configures the extra directory. */
-public class ExtraDirectoryParameters {
+/** Object in {@link JibExtension} that configures the extra directories. */
+public class ExtraDirectoriesParameters {
 
   private final Project project;
+  @Deprecated private final JibExtension jibExtension;
 
   private List<Path> paths;
   private Map<String, String> permissions = Collections.emptyMap();
 
   @Inject
-  public ExtraDirectoryParameters(Project project) {
+  public ExtraDirectoriesParameters(Project project, JibExtension jibExtension) {
     this.project = project;
+    this.jibExtension = jibExtension;
     paths =
         Collections.singletonList(
             project.getProjectDir().toPath().resolve("src").resolve("main").resolve("jib"));
@@ -57,7 +59,9 @@ public List<String> getPathStrings() {
   public List<Path> getPaths() {
     // Gradle warns about @Input annotations on File objects, so we have to expose a getter for a
     // String to make them go away.
-    String property = System.getProperty(PropertyNames.EXTRA_DIRECTORY_PATH);
+    String deprecatedProperty = System.getProperty(PropertyNames.EXTRA_DIRECTORY_PATH);
+    String newProperty = System.getProperty(PropertyNames.EXTRA_DIRECTORIES_PATHS);
+    String property = newProperty != null ? newProperty : deprecatedProperty;
     if (property != null) {
       List<String> pathStrings = ConfigurationPropertyValidator.parseListProperty(property);
       return pathStrings.stream().map(Paths::get).collect(Collectors.toList());
@@ -67,16 +71,22 @@ public List<Path> getPaths() {
 
   /**
    * Sets paths. {@code paths} can be any suitable object describing file paths convertible by
-   * {@link Project#files} (such as {@code List<File>}).
+   * {@link Project#files} (such as {@link File}, {@code List<File>}, or {@code List<String>}).
    *
    * @param paths paths to set.
    */
-  // non-plural to retain backward-compatibility for the "jib.extraDirectory.path" config parameter
-  public void setPath(Object paths) {
+  public void setPaths(Object paths) {
+    jibExtension.extraDirectoriesConfigured = true;
     this.paths =
         project.files(paths).getFiles().stream().map(File::toPath).collect(Collectors.toList());
   }
 
+  @Deprecated
+  public void setPath(File path) {
+    jibExtension.extraDirectoryConfigured = true;
+    this.paths = Collections.singletonList(path.toPath());
+  }
+
   /**
    * Gets the permissions for files in the extra layer on the container. Maps from absolute path on
    * the container to a 3-digit octal string representation of the file permission bits (e.g. {@code
@@ -86,9 +96,11 @@ public void setPath(Object paths) {
    */
   @Input
   public Map<String, String> getPermissions() {
-    if (System.getProperty(PropertyNames.EXTRA_DIRECTORY_PERMISSIONS) != null) {
-      return ConfigurationPropertyValidator.parseMapProperty(
-          System.getProperty(PropertyNames.EXTRA_DIRECTORY_PERMISSIONS));
+    String deprecatedProperty = System.getProperty(PropertyNames.EXTRA_DIRECTORY_PERMISSIONS);
+    String newProperty = System.getProperty(PropertyNames.EXTRA_DIRECTORIES_PERMISSIONS);
+    String property = newProperty != null ? newProperty : deprecatedProperty;
+    if (property != null) {
+      return ConfigurationPropertyValidator.parseMapProperty(property);
     }
     return permissions;
   }
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTask.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTask.java
index d59523fe4b..e32ad05486 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTask.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTask.java
@@ -150,7 +150,7 @@ public void listFiles() {
     printProjectFiles(project);
 
     // Print extra layer
-    List<Path> extraDirectories = jibExtension.getExtraDirectory().getPaths();
+    List<Path> extraDirectories = jibExtension.getExtraDirectories().getPaths();
     extraDirectories.stream().filter(Files::exists).forEach(System.out::println);
 
     // Find project dependencies
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTaskV2.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTaskV2.java
index 1d8e4a4a6a..6c5b2938a4 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTaskV2.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/FilesTaskV2.java
@@ -69,7 +69,7 @@ public void listFiles() throws IOException {
     addProjectFiles(project);
 
     // Add extra layer
-    List<Path> extraDirectories = jibExtension.getExtraDirectory().getPaths();
+    List<Path> extraDirectories = jibExtension.getExtraDirectories().getPaths();
     extraDirectories.stream().filter(Files::exists).forEach(skaffoldFilesOutput::addInput);
 
     // Find project dependencies
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/GradleRawConfiguration.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/GradleRawConfiguration.java
index de7ae2fd03..eed3b424a3 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/GradleRawConfiguration.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/GradleRawConfiguration.java
@@ -152,11 +152,11 @@ public Optional<String> getProperty(String propertyName) {
 
   @Override
   public List<Path> getExtraDirectories() {
-    return jibExtension.getExtraDirectory().getPaths();
+    return jibExtension.getExtraDirectories().getPaths();
   }
 
   @Override
   public Map<AbsoluteUnixPath, FilePermissions> getExtraDirectoryPermissions() {
-    return TaskCommon.convertPermissionsMap(jibExtension.getExtraDirectory().getPermissions());
+    return TaskCommon.convertPermissionsMap(jibExtension.getExtraDirectories().getPermissions());
   }
 }
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/JibExtension.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/JibExtension.java
index 70d35d5255..d7760e0004 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/JibExtension.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/JibExtension.java
@@ -17,6 +17,7 @@
 package com.google.cloud.tools.jib.gradle;
 
 import com.google.cloud.tools.jib.plugins.common.PropertyNames;
+import java.io.File;
 import org.gradle.api.Action;
 import org.gradle.api.Project;
 import org.gradle.api.model.ObjectFactory;
@@ -48,8 +49,8 @@
  *     format = OCI
  *     appRoot = '/app'
  *   }
- *   extraDirectory {
- *     path = file('path/to/extra/dir')
+ *   extraDirectories {
+ *     paths = ['/path/to/extra/dir', 'can/be/relative/to/project/root']
  *     permissions = [
  *       '/path/on/container/file1': 744,
  *       '/path/on/container/file2': 123
@@ -67,17 +68,19 @@ public class JibExtension {
   private final BaseImageParameters from;
   private final TargetImageParameters to;
   private final ContainerParameters container;
-  private final ExtraDirectoryParameters extraDirectory;
-
+  private final ExtraDirectoriesParameters extraDirectories;
   private final Property<Boolean> allowInsecureRegistries;
 
+  @Deprecated boolean extraDirectoryConfigured;
+  @Deprecated boolean extraDirectoriesConfigured;
+
   public JibExtension(Project project) {
     ObjectFactory objectFactory = project.getObjects();
 
     from = objectFactory.newInstance(BaseImageParameters.class);
     to = objectFactory.newInstance(TargetImageParameters.class);
     container = objectFactory.newInstance(ContainerParameters.class);
-    extraDirectory = objectFactory.newInstance(ExtraDirectoryParameters.class, project);
+    extraDirectories = objectFactory.newInstance(ExtraDirectoriesParameters.class, project, this);
 
     allowInsecureRegistries = objectFactory.property(Boolean.class);
 
@@ -97,19 +100,22 @@ public void container(Action<? super ContainerParameters> action) {
     action.execute(container);
   }
 
-  public void extraDirectory(Action<? super ExtraDirectoryParameters> action) {
-    action.execute(extraDirectory);
+  @Deprecated
+  public void extraDirectory(Action<? super ExtraDirectoriesParameters> action) {
+    extraDirectoryConfigured = true;
+    action.execute(extraDirectories);
+  }
+
+  public void extraDirectories(Action<? super ExtraDirectoriesParameters> action) {
+    extraDirectoriesConfigured = true;
+    action.execute(extraDirectories);
   }
 
-  /**
-   * Sets extra directory paths. {@code extraDirectories} can be any suitable object describing file
-   * paths convertible by {@link Project#files} (such as {@code List<File>}).
-   *
-   * @param extraDirectories paths to set.
-   */
-  // non-plural to retain backward-compatibility for the "jib.extraDirectory" config parameter
-  public void setExtraDirectory(Object extraDirectories) {
-    this.extraDirectory.setPath(extraDirectories);
+  @Deprecated
+  // for the deprecated "jib.extraDirectory" config parameter
+  public void setExtraDirectory(File extraDirectory) {
+    extraDirectoryConfigured = true;
+    this.extraDirectories.setPath(extraDirectory);
   }
 
   public void setAllowInsecureRegistries(boolean allowInsecureRegistries) {
@@ -134,10 +140,17 @@ public ContainerParameters getContainer() {
     return container;
   }
 
+  @Deprecated
+  @Nested
+  @Optional
+  public ExtraDirectoriesParameters getExtraDirectory() {
+    return extraDirectories;
+  }
+
   @Nested
   @Optional
-  public ExtraDirectoryParameters getExtraDirectory() {
-    return extraDirectory;
+  public ExtraDirectoriesParameters getExtraDirectories() {
+    return extraDirectories;
   }
 
   @Input
diff --git a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/TaskCommon.java b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/TaskCommon.java
index 3464a0d197..8b7ef5654d 100644
--- a/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/TaskCommon.java
+++ b/jib-gradle-plugin/src/main/java/com/google/cloud/tools/jib/gradle/TaskCommon.java
@@ -19,12 +19,13 @@
 import com.google.api.client.http.HttpTransport;
 import com.google.cloud.tools.jib.configuration.FilePermissions;
 import com.google.cloud.tools.jib.filesystem.AbsoluteUnixPath;
-import com.google.common.annotations.VisibleForTesting;
+import com.google.cloud.tools.jib.plugins.common.PropertyNames;
 import java.util.HashMap;
 import java.util.Map;
 import java.util.logging.Level;
 import javax.annotation.Nullable;
 import org.gradle.api.Project;
+import org.gradle.api.logging.Logger;
 import org.gradle.api.plugins.WarPluginConvention;
 import org.gradle.api.tasks.bundling.War;
 import org.gradle.internal.logging.events.LogEvent;
@@ -67,6 +68,25 @@ static void disableHttpLogging() {
     java.util.logging.Logger.getLogger(HttpTransport.class.getName()).setLevel(Level.OFF);
   }
 
+  @Deprecated
+  static void checkDeprecatedUsage(JibExtension jibExtension, Logger logger) {
+    if (jibExtension.extraDirectoryConfigured
+        || System.getProperty(PropertyNames.EXTRA_DIRECTORY_PATH) != null
+        || System.getProperty(PropertyNames.EXTRA_DIRECTORY_PERMISSIONS) != null) {
+      logger.warn(
+          "'jib.extraDirectory', 'jib.extraDirectory.path', and 'jib.extraDirectory.permissions' "
+              + "are deprecated; use 'jib.extraDirectories.paths' and "
+              + "'jib.extraDirectories.permissions'");
+
+      if (jibExtension.extraDirectoriesConfigured
+          || System.getProperty(PropertyNames.EXTRA_DIRECTORIES_PATHS) != null
+          || System.getProperty(PropertyNames.EXTRA_DIRECTORIES_PERMISSIONS) != null) {
+        throw new IllegalArgumentException(
+            "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'");
+      }
+    }
+  }
+
   /**
    * Validates and converts a {@code String->String} file-path-to-file-permissions map to an
    * equivalent {@code AbsoluteUnixPath->FilePermission} map.
@@ -74,7 +94,6 @@ static void disableHttpLogging() {
    * @param stringMap the map to convert (example entry: {@code "/path/on/container" -> "755"})
    * @return the converted map
    */
-  @VisibleForTesting
   static Map<AbsoluteUnixPath, FilePermissions> convertPermissionsMap(
       Map<String, String> stringMap) {
     Map<AbsoluteUnixPath, FilePermissions> permissionsMap = new HashMap<>();
diff --git a/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/JibExtensionTest.java b/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/JibExtensionTest.java
index c4ca5edbb9..40aab0338a 100644
--- a/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/JibExtensionTest.java
+++ b/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/JibExtensionTest.java
@@ -56,6 +56,8 @@ private static void clearProperties() {
     System.clearProperty("jib.container.user");
     System.clearProperty("jib.extraDirectory.path");
     System.clearProperty("jib.extraDirectory.permissions");
+    System.clearProperty("jib.extraDirectories.paths");
+    System.clearProperty("jib.extraDirectories.permissions");
   }
 
   @Before
@@ -151,24 +153,90 @@ public void testContainer() {
   }
 
   @Test
-  public void testExtraDirectory() {
+  public void testExtraDirectories_default() {
     Assert.assertEquals(
         Arrays.asList(Paths.get(fakeProject.getProjectDir().getPath(), "src", "main", "jib")),
-        testJibExtension.getExtraDirectory().getPaths());
+        testJibExtension.getExtraDirectories().getPaths());
     Assert.assertEquals(
-        Collections.emptyMap(), testJibExtension.getExtraDirectory().getPermissions());
+        Collections.emptyMap(), testJibExtension.getExtraDirectories().getPermissions());
+  }
 
+  @Test
+  public void testExtraDirectories_deprecatedConfig() {
     testJibExtension.extraDirectory(
         extraDirectory -> {
           extraDirectory.setPath(Paths.get("test", "path").toFile());
           extraDirectory.setPermissions(ImmutableMap.of("file1", "123", "file2", "456"));
         });
+    Assert.assertTrue(testJibExtension.extraDirectoryConfigured);
+    Assert.assertFalse(testJibExtension.extraDirectoriesConfigured);
+
+    Assert.assertEquals(
+        Arrays.asList(Paths.get("test", "path")),
+        testJibExtension.getExtraDirectories().getPaths());
+    Assert.assertEquals(
+        ImmutableMap.of("file1", "123", "file2", "456"),
+        testJibExtension.getExtraDirectories().getPermissions());
+  }
+
+  @Test
+  public void testExtraDirectories() {
+    testJibExtension.extraDirectories(
+        extraDirectories -> {
+          extraDirectories.setPaths("test/path");
+          extraDirectories.setPermissions(ImmutableMap.of("file1", "123", "file2", "456"));
+        });
+    Assert.assertFalse(testJibExtension.extraDirectoryConfigured);
+    Assert.assertTrue(testJibExtension.extraDirectoriesConfigured);
+
     Assert.assertEquals(
         Arrays.asList(Paths.get(fakeProject.getProjectDir().getPath(), "test", "path")),
-        testJibExtension.getExtraDirectory().getPaths());
+        testJibExtension.getExtraDirectories().getPaths());
     Assert.assertEquals(
         ImmutableMap.of("file1", "123", "file2", "456"),
-        testJibExtension.getExtraDirectory().getPermissions());
+        testJibExtension.getExtraDirectories().getPermissions());
+  }
+
+  @Test
+  public void testExtraDirectories_fileForPaths() {
+    testJibExtension.extraDirectories(
+        extraDirectories -> {
+          extraDirectories.setPaths(Paths.get("test", "path").toFile());
+        });
+    Assert.assertEquals(
+        Arrays.asList(Paths.get(fakeProject.getProjectDir().getPath(), "test", "path")),
+        testJibExtension.getExtraDirectories().getPaths());
+  }
+
+  @Test
+  public void testExtraDirectories_stringListForPaths() {
+    testJibExtension.extraDirectories(
+        extraDirectories -> {
+          extraDirectories.setPaths(Arrays.asList("test/path", "another/path"));
+          extraDirectories.setPermissions(ImmutableMap.of("file1", "123", "file2", "456"));
+        });
+
+    String projectRoot = fakeProject.getProjectDir().getPath();
+    Assert.assertEquals(
+        Arrays.asList(
+            Paths.get(projectRoot, "test", "path"), Paths.get(projectRoot, "another", "path")),
+        testJibExtension.getExtraDirectories().getPaths());
+  }
+
+  @Test
+  public void testExtraDirectories_fileListForPaths() {
+    testJibExtension.extraDirectories(
+        extraDirectories -> {
+          extraDirectories.setPaths(
+              Arrays.asList(
+                  Paths.get("test", "path").toFile(), Paths.get("another", "path").toFile()));
+        });
+
+    String projectRoot = fakeProject.getProjectDir().getPath();
+    Assert.assertEquals(
+        Arrays.asList(
+            Paths.get(projectRoot, "test", "path"), Paths.get(projectRoot, "another", "path")),
+        testJibExtension.getExtraDirectories().getPaths());
   }
 
   @Test
@@ -220,5 +288,25 @@ public void testProperties() {
     Assert.assertTrue(testJibExtension.getContainer().getUseCurrentTimestamp());
     System.setProperty("jib.container.user", "myUser");
     Assert.assertEquals("myUser", testJibExtension.getContainer().getUser());
+    System.setProperty("jib.extraDirectories.paths", "/foo,/bar/baz");
+    Assert.assertEquals(
+        Arrays.asList(Paths.get("/foo"), Paths.get("/bar/baz")),
+        testJibExtension.getExtraDirectories().getPaths());
+    System.setProperty("jib.extraDirectories.permissions", "/foo/bar=707,/baz=456");
+    Assert.assertEquals(
+        ImmutableMap.of("/foo/bar", "707", "/baz", "456"),
+        testJibExtension.getExtraDirectories().getPermissions());
+  }
+
+  @Test
+  public void testDeprecatedProperties() {
+    System.setProperty("jib.extraDirectory.path", "/foo,/bar/baz");
+    Assert.assertEquals(
+        Arrays.asList(Paths.get("/foo"), Paths.get("/bar/baz")),
+        testJibExtension.getExtraDirectories().getPaths());
+    System.setProperty("jib.extraDirectory.permissions", "/foo/bar=707,/baz=456");
+    Assert.assertEquals(
+        ImmutableMap.of("/foo/bar", "707", "/baz", "456"),
+        testJibExtension.getExtraDirectories().getPermissions());
   }
 }
diff --git a/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/TaskCommonTest.java b/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/TaskCommonTest.java
new file mode 100644
index 0000000000..882c213a75
--- /dev/null
+++ b/jib-gradle-plugin/src/test/java/com/google/cloud/tools/jib/gradle/TaskCommonTest.java
@@ -0,0 +1,126 @@
+/*
+ * Copyright 2019 Google LLC.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License"); you may not
+ * use this file except in compliance with the License. You may obtain a copy of
+ * the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS, WITHOUT
+ * WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
+ * License for the specific language governing permissions and limitations under
+ * the License.
+ */
+
+package com.google.cloud.tools.jib.gradle;
+
+import org.gradle.api.logging.Logger;
+import org.junit.After;
+import org.junit.Assert;
+import org.junit.Before;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+import org.mockito.Mock;
+import org.mockito.Mockito;
+import org.mockito.junit.MockitoJUnitRunner;
+
+/** Tests for {@link TaskCommon}. */
+@RunWith(MockitoJUnitRunner.class)
+public class TaskCommonTest {
+
+  @Mock private JibExtension jibExtension;
+  @Mock private Logger logger;
+
+  @Before
+  public void setUp() {
+    Assert.assertNull(System.getProperty("jib.extraDirectory.path"));
+    Assert.assertNull(System.getProperty("jib.extraDirectory.permissions"));
+    Assert.assertNull(System.getProperty("jib.extraDirectories.paths"));
+    Assert.assertNull(System.getProperty("jib.extraDirectories.permissions"));
+  }
+
+  @After
+  public void tearDown() {
+    System.clearProperty("jib.extraDirectory.path");
+    System.clearProperty("jib.extraDirectory.permissions");
+    System.clearProperty("jib.extraDirectories.paths");
+    System.clearProperty("jib.extraDirectories.permissions");
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_default() {
+    TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+    Mockito.verify(logger, Mockito.never()).warn(Mockito.anyString());
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_extraDirectoriesConfigured() {
+    jibExtension.extraDirectoriesConfigured = true;
+    TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+    Mockito.verify(logger, Mockito.never()).warn(Mockito.anyString());
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_extraDirectoryPathPropertySet() {
+    System.setProperty("jib.extraDirectory.path", "something");
+    TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+    Mockito.verify(logger, Mockito.times(1))
+        .warn(
+            "'jib.extraDirectory', 'jib.extraDirectory.path', and 'jib.extraDirectory.permissions' "
+                + "are deprecated; use 'jib.extraDirectories.paths' and "
+                + "'jib.extraDirectories.permissions'");
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_extraDirectoryPermissionsPropertySet() {
+    System.setProperty("jib.extraDirectory.permissions", "something");
+    TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+    Mockito.verify(logger, Mockito.times(1))
+        .warn(
+            "'jib.extraDirectory', 'jib.extraDirectory.path', and 'jib.extraDirectory.permissions' "
+                + "are deprecated; use 'jib.extraDirectories.paths' and "
+                + "'jib.extraDirectories.permissions'");
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_extraDirectoryAndExtraDirectoriesPropertiesSet() {
+    System.setProperty("jib.extraDirectory.path", "something");
+    System.setProperty("jib.extraDirectories.permissions", "something");
+
+    try {
+      TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+      Assert.fail();
+    } catch (IllegalArgumentException ex) {
+      Assert.assertEquals(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'",
+          ex.getMessage());
+    }
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_extraDirectoryConfigured() {
+    jibExtension.extraDirectoryConfigured = true;
+    TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+    Mockito.verify(logger, Mockito.times(1))
+        .warn(
+            "'jib.extraDirectory', 'jib.extraDirectory.path', and 'jib.extraDirectory.permissions' "
+                + "are deprecated; use 'jib.extraDirectories.paths' and "
+                + "'jib.extraDirectories.permissions'");
+  }
+
+  @Test
+  public void testCheckDeprecatedUsage_extraDirectoryAndExtraDirectoriesConfigured() {
+    jibExtension.extraDirectoryConfigured = true;
+    jibExtension.extraDirectoriesConfigured = true;
+    try {
+      TaskCommon.checkDeprecatedUsage(jibExtension, logger);
+      Assert.fail();
+    } catch (IllegalArgumentException ex) {
+      Assert.assertEquals(
+          "You cannot configure both 'jib.extraDirectory.path' and 'jib.extraDirectories.paths'",
+          ex.getMessage());
+    }
+  }
+}
diff --git a/jib-gradle-plugin/src/test/resources/gradle/projects/multi-service/complex-service/build.gradle b/jib-gradle-plugin/src/test/resources/gradle/projects/multi-service/complex-service/build.gradle
index 92ca5a3e66..eacc676f1c 100644
--- a/jib-gradle-plugin/src/test/resources/gradle/projects/multi-service/complex-service/build.gradle
+++ b/jib-gradle-plugin/src/test/resources/gradle/projects/multi-service/complex-service/build.gradle
@@ -17,8 +17,8 @@ jib {
   to {
     image = System.getProperty("_TARGET_IMAGE")
   }
-  extraDirectory {
-    path = file('src/main/other-jib')
+  extraDirectories {
+    paths = file('src/main/other-jib')
   }
 }
 
@@ -34,4 +34,4 @@ dependencies {
   compile project(':lib')
   compile 'org.apache.commons:commons-io:1.3.2'
   compile 'com.google.guava:guava:HEAD-jre-SNAPSHOT'
-}
\ No newline at end of file
+}
diff --git a/jib-gradle-plugin/src/test/resources/gradle/projects/simple/build.gradle b/jib-gradle-plugin/src/test/resources/gradle/projects/simple/build.gradle
index 52d0f7cab5..6dab9e5207 100644
--- a/jib-gradle-plugin/src/test/resources/gradle/projects/simple/build.gradle
+++ b/jib-gradle-plugin/src/test/resources/gradle/projects/simple/build.gradle
@@ -18,7 +18,7 @@ jib {
   to {
     image = System.getProperty("_TARGET_IMAGE")
   }
-  extraDirectory {
-    path = file('src/main/custom-extra-dir')
+  extraDirectories {
+    paths = file('src/main/custom-extra-dir')
   }
 }
diff --git a/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-complex-properties.xml b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-complex-properties.xml
index 9e392e7e84..b8c1dc77e3 100644
--- a/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-complex-properties.xml
+++ b/jib-maven-plugin/src/test/resources/maven/projects/simple/pom-complex-properties.xml
@@ -27,8 +27,8 @@
     <jib.container.labels>key1=value1,key2=value2</jib.container.labels>
     <jib.container.volumes>/var/log,/var/log2</jib.container.volumes>
     <jib.container.format>Docker</jib.container.format>
-    <jib.extraDirectory.path>${project.basedir}/src/main/jib-custom</jib.extraDirectory.path>
-    <jib.extraDirectory.permissions>/foo=755,/bar/cat=777</jib.extraDirectory.permissions>
+    <jib.extraDirectories.paths>${project.basedir}/src/main/jib-custom</jib.extraDirectories.paths>
+    <jib.extraDirectories.permissions>/foo=755,/bar/cat=777</jib.extraDirectories.permissions>
     <jib.allowInsecureRegistries>true</jib.allowInsecureRegistries>
   </properties>