diff --git a/features/plugin-update.feature b/features/plugin-update.feature
index 1cf5e248..7f7e1e5e 100644
--- a/features/plugin-update.feature
+++ b/features/plugin-update.feature
@@ -268,6 +268,94 @@ Feature: Update WordPress plugins
       Success: Updated 1 of 1 plugins (1 skipped).
       """
 
+  # Tests for --auto-update-indicated feature
+  # Note: These tests verify the flag handling and error cases.
+  # The actual update behavior when autoupdate is true from the server
+  # cannot be easily tested as it requires mocking WordPress.org API responses.
+  # The update functionality itself is handled by the existing update_many method.
+
+  @require-wp-5.2
+  Scenario: Show auto_update_indicated field in plugin list
+    Given a WP install
+
+    When I run `wp plugin install wordpress-importer --version=0.5 --force`
+    Then STDOUT should not be empty
+
+    When I run `wp plugin list --fields=name,version,update,auto_update_indicated`
+    Then STDOUT should be a table containing rows:
+      | name               | version | update    | auto_update_indicated |
+      | wordpress-importer | 0.5     | available | no                    |
+
+  @require-wp-5.2
+  Scenario: Using --auto-update-indicated flag when no plugins have auto-update indicated
+    Given a WP install
+
+    When I run `wp plugin install wordpress-importer --version=0.5 --force`
+    Then STDOUT should not be empty
+
+    When I run `wp plugin update --auto-update-indicated`
+    Then STDOUT should be:
+      """
+      Success: No plugins with server-indicated automatic updates available.
+      """
+
+  @require-wp-5.2
+  Scenario: Error when using --version with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp plugin update --auto-update-indicated --version=1.0.0`
+    Then STDERR should be:
+      """
+      Error: Cannot use --version with --auto-update-indicated. The version is determined by the server.
+      """
+    And the return code should be 1
+
+  @require-wp-5.2
+  Scenario: Error when using --minor with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp plugin update --auto-update-indicated --minor`
+    Then STDERR should be:
+      """
+      Error: Cannot use --minor or --patch with --auto-update-indicated. The version is determined by the server.
+      """
+    And the return code should be 1
+
+  @require-wp-5.2
+  Scenario: Error when using --patch with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp plugin update --auto-update-indicated --patch`
+    Then STDERR should be:
+      """
+      Error: Cannot use --minor or --patch with --auto-update-indicated. The version is determined by the server.
+      """
+    And the return code should be 1
+
+  @require-wp-5.2
+  Scenario: Error when specifying plugin names with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp plugin update akismet --auto-update-indicated`
+    Then STDERR should be:
+      """
+      Error: Cannot specify plugin names with --auto-update-indicated. This flag updates all plugins with server-indicated automatic updates.
+      """
+    And the return code should be 1
+
+  @require-wp-5.2
+  Scenario: Preview updates with --auto-update-indicated and --dry-run
+    Given a WP install
+
+    When I run `wp plugin install wordpress-importer --version=0.5 --force`
+    Then STDOUT should not be empty
+
+    When I run `wp plugin update --auto-update-indicated --dry-run`
+    Then STDOUT should be:
+      """
+      Success: No plugins with server-indicated automatic updates available.
+      """
+
   @require-wp-5.2
   Scenario: Updating all plugins should show the name of each plugin as it is updated
     Given a WP install
diff --git a/features/theme-update.feature b/features/theme-update.feature
index adc546b0..a71fdb1a 100644
--- a/features/theme-update.feature
+++ b/features/theme-update.feature
@@ -155,6 +155,87 @@ Feature: Update WordPress themes
       1.1.1
       """
 
+  # Tests for --auto-update-indicated feature
+  # Note: These tests verify the flag handling and error cases.
+  # The actual update behavior when autoupdate is true from the server
+  # cannot be easily tested as it requires mocking WordPress.org API responses.
+  # The update functionality itself is handled by the existing update_many method.
+
+  Scenario: Show auto_update_indicated field in theme list
+    Given a WP install
+
+    When I run `wp theme install twentytwelve --version=3.0 --force`
+    Then STDOUT should not be empty
+
+    When I run `wp theme list --fields=name,version,update,auto_update_indicated`
+    Then STDOUT should be a table containing rows:
+      | name         | version | update    | auto_update_indicated |
+      | twentytwelve | 3.0     | available | no                    |
+
+  Scenario: Using --auto-update-indicated flag when no themes have auto-update indicated
+    Given a WP install
+
+    When I run `wp theme install twentytwelve --version=3.0 --force`
+    Then STDOUT should not be empty
+
+    When I run `wp theme update --auto-update-indicated`
+    Then STDOUT should be:
+      """
+      Success: No themes with server-indicated automatic updates available.
+      """
+
+  Scenario: Error when using --version with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp theme update --auto-update-indicated --version=1.0.0`
+    Then STDERR should be:
+      """
+      Error: Cannot use --version with --auto-update-indicated. The version is determined by the server.
+      """
+    And the return code should be 1
+
+  Scenario: Error when using --minor with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp theme update --auto-update-indicated --minor`
+    Then STDERR should be:
+      """
+      Error: Cannot use --minor or --patch with --auto-update-indicated. The version is determined by the server.
+      """
+    And the return code should be 1
+
+  Scenario: Error when using --patch with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp theme update --auto-update-indicated --patch`
+    Then STDERR should be:
+      """
+      Error: Cannot use --minor or --patch with --auto-update-indicated. The version is determined by the server.
+      """
+    And the return code should be 1
+
+  Scenario: Error when specifying theme names with --auto-update-indicated
+    Given a WP install
+
+    When I try `wp theme update twentytwelve --auto-update-indicated`
+    Then STDERR should be:
+      """
+      Error: Cannot specify theme names with --auto-update-indicated. This flag updates all themes with server-indicated automatic updates.
+      """
+    And the return code should be 1
+
+  Scenario: Preview updates with --auto-update-indicated and --dry-run
+    Given a WP install
+
+    When I run `wp theme install twentytwelve --version=3.0 --force`
+    Then STDOUT should not be empty
+
+    When I run `wp theme update --auto-update-indicated --dry-run`
+    Then STDOUT should be:
+      """
+      Success: No themes with server-indicated automatic updates available.
+      """
+
   @require-wp-4.5
   Scenario: Updating all themes should show the name of each theme as it is updated
     Given a WP install
diff --git a/src/Plugin_Command.php b/src/Plugin_Command.php
index ae04e702..7930bfdd 100644
--- a/src/Plugin_Command.php
+++ b/src/Plugin_Command.php
@@ -726,6 +726,9 @@ protected function install_from_repo( $slug, $assoc_args ) {
 	 * [--insecure]
 	 * : Retry downloads without certificate validation if TLS handshake fails. Note: This makes the request vulnerable to a MITM attack.
 	 *
+	 * [--auto-update-indicated]
+	 * : Only update plugins where the server response indicates an automatic update. Updates to the version indicated by the server, not necessarily the latest version. Cannot be used with `--version`, `--minor`, or `--patch`.
+	 *
 	 * ## EXAMPLES
 	 *
 	 *     $ wp plugin update bbpress --version=dev
@@ -777,6 +780,11 @@ protected function install_from_repo( $slug, $assoc_args ) {
 	public function update( $args, $assoc_args ) {
 		$all = Utils\get_flag_value( $assoc_args, 'all', false );
 
+		// Handle --auto-update-indicated flag if present.
+		if ( $this->handle_auto_update_indicated( $args, $assoc_args ) ) {
+			return;
+		}
+
 		$args = $this->check_optional_args_and_all( $args, $all );
 		if ( ! $args ) {
 			return;
@@ -825,8 +833,9 @@ protected function get_item_list() {
 				$duplicate_names[ $name ] = array();
 			}
 
-			$requires     = isset( $update_info ) && isset( $update_info['requires'] ) ? $update_info['requires'] : null;
-			$requires_php = isset( $update_info ) && isset( $update_info['requires_php'] ) ? $update_info['requires_php'] : null;
+			$requires              = isset( $update_info ) && isset( $update_info['requires'] ) ? $update_info['requires'] : null;
+			$requires_php          = isset( $update_info ) && isset( $update_info['requires_php'] ) ? $update_info['requires_php'] : null;
+			$auto_update_indicated = isset( $update_info ) && isset( $update_info['autoupdate'] ) ? (bool) $update_info['autoupdate'] : false;
 
 			// If an update has requires_php set, check to see if the local version of PHP meets that requirement
 			// The plugins update API already filters out plugins that don't meet WordPress requirements, but does not
@@ -868,6 +877,7 @@ protected function get_item_list() {
 				'description'               => wordwrap( $details['Description'] ),
 				'file'                      => $file,
 				'auto_update'               => in_array( $file, $auto_updates, true ),
+				'auto_update_indicated'     => $auto_update_indicated,
 				'author'                    => $details['Author'],
 				'tested_up_to'              => '',
 				'requires'                  => $requires,
@@ -1794,6 +1804,7 @@ public function delete( $args, $assoc_args ) {
 	 * * requires_php
 	 * * wporg_status
 	 * * wporg_last_updated
+	 * * auto_update_indicated
 	 *
 	 * ## EXAMPLES
 	 *
diff --git a/src/Theme_Command.php b/src/Theme_Command.php
index e18b17e8..f276ec41 100644
--- a/src/Theme_Command.php
+++ b/src/Theme_Command.php
@@ -691,6 +691,9 @@ public function get( $args, $assoc_args ) {
 	 * [--insecure]
 	 * : Retry downloads without certificate validation if TLS handshake fails. Note: This makes the request vulnerable to a MITM attack.
 	 *
+	 * [--auto-update-indicated]
+	 * : Only update themes where the server response indicates an automatic update. Updates to the version indicated by the server, not necessarily the latest version. Cannot be used with `--version`, `--minor`, or `--patch`.
+	 *
 	 * ## EXAMPLES
 	 *
 	 *     # Update multiple themes
@@ -741,6 +744,11 @@ public function get( $args, $assoc_args ) {
 	public function update( $args, $assoc_args ) {
 		$all = Utils\get_flag_value( $assoc_args, 'all', false );
 
+		// Handle --auto-update-indicated flag if present.
+		if ( $this->handle_auto_update_indicated( $args, $assoc_args ) ) {
+			return;
+		}
+
 		$args = $this->check_optional_args_and_all( $args, $all );
 		if ( ! $args ) {
 			return;
@@ -945,6 +953,7 @@ public function delete( $args, $assoc_args ) {
 	 * * update_id
 	 * * title
 	 * * description
+	 * * auto_update_indicated
 	 *
 	 * ## EXAMPLES
 	 *
diff --git a/src/WP_CLI/CommandWithUpgrade.php b/src/WP_CLI/CommandWithUpgrade.php
index fe1126ca..d1623c97 100755
--- a/src/WP_CLI/CommandWithUpgrade.php
+++ b/src/WP_CLI/CommandWithUpgrade.php
@@ -562,6 +562,62 @@ protected function get_upgrader( $assoc_args ) {
 		return Utils\get_upgrader( $upgrader_class, $insecure, new ExtensionUpgraderSkin() );
 	}
 
+	/**
+	 * Handles the --auto-update-indicated flag logic for both plugins and themes.
+	 *
+	 * This method validates flag combinations, filters items by auto_update_indicated,
+	 * and processes updates if any items are found.
+	 *
+	 * @param array $args        Positional arguments (item names).
+	 * @param array $assoc_args  Associative arguments (flags).
+	 * @return bool              Returns true if auto-update-indicated was handled, false otherwise.
+	 */
+	protected function handle_auto_update_indicated( $args, $assoc_args ) {
+		$auto_update_indicated = Utils\get_flag_value( $assoc_args, 'auto-update-indicated', false );
+
+		if ( ! $auto_update_indicated ) {
+			return false;
+		}
+
+		// Don't allow --version to be set with --auto-update-indicated, as the version comes from the server.
+		if ( isset( $assoc_args['version'] ) ) {
+			WP_CLI::error( 'Cannot use --version with --auto-update-indicated. The version is determined by the server.' );
+		}
+
+		// Don't allow --minor or --patch to be set with --auto-update-indicated, as the version comes from the server.
+		if ( isset( $assoc_args['minor'] ) || isset( $assoc_args['patch'] ) ) {
+			WP_CLI::error( 'Cannot use --minor or --patch with --auto-update-indicated. The version is determined by the server.' );
+		}
+
+		// Don't allow item names to be specified with --auto-update-indicated.
+		if ( ! empty( $args ) ) {
+			WP_CLI::error( "Cannot specify {$this->item_type} names with --auto-update-indicated. This flag updates all {$this->item_type}s with server-indicated automatic updates." );
+		}
+
+		// Get all items with their update info.
+		$items = $this->get_item_list();
+
+		// Filter to only include items where auto_update_indicated is true.
+		$auto_update_items = array_filter(
+			$items,
+			function ( $item ) {
+				return ! empty( $item['auto_update_indicated'] );
+			}
+		);
+
+		// Get the item names to update.
+		$args = array_values( wp_list_pluck( $auto_update_items, 'name' ) );
+
+		if ( empty( $args ) ) {
+			WP_CLI::success( "No {$this->item_type}s with server-indicated automatic updates available." );
+			return true;
+		}
+
+		// Process the updates.
+		$this->update_many( $args, $assoc_args );
+		return true;
+	}
+
 	protected function update_many( $args, $assoc_args ) {
 		call_user_func( $this->upgrade_refresh );
 
@@ -812,6 +868,12 @@ function ( $value ) {
 					} elseif ( false === $value ) {
 						$value = 'off';
 					}
+				} elseif ( 'auto_update_indicated' === $field ) {
+					if ( true === $value ) {
+						$value = 'yes';
+					} elseif ( false === $value ) {
+						$value = 'no';
+					}
 				}
 			}
 
diff --git a/src/WP_CLI/ParseThemeNameInput.php b/src/WP_CLI/ParseThemeNameInput.php
index 2c177f2f..b0bc1ae6 100644
--- a/src/WP_CLI/ParseThemeNameInput.php
+++ b/src/WP_CLI/ParseThemeNameInput.php
@@ -90,8 +90,9 @@ private function get_all_themes() {
 		}
 
 		foreach ( wp_get_themes( [ 'errors' => null ] ) as $key => $theme ) {
-			$stylesheet  = $theme->get_stylesheet();
-			$update_info = ( isset( $all_update_info->response[ $stylesheet ] ) && null !== $all_update_info->response[ $theme->get_stylesheet() ] ) ? (array) $all_update_info->response[ $theme->get_stylesheet() ] : null;
+			$stylesheet            = $theme->get_stylesheet();
+			$update_info           = ( isset( $all_update_info->response[ $stylesheet ] ) && null !== $all_update_info->response[ $theme->get_stylesheet() ] ) ? (array) $all_update_info->response[ $theme->get_stylesheet() ] : null;
+			$auto_update_indicated = isset( $update_info ) && isset( $update_info['autoupdate'] ) ? (bool) $update_info['autoupdate'] : false;
 
 			// Unlike plugin update responses, the wordpress.org API does not seem to check and filter themes that don't meet
 			// WordPress version requirements into a separate no_updates array
@@ -149,6 +150,7 @@ private function get_all_themes() {
 				'description'               => wordwrap( $theme->get( 'Description' ) ),
 				'author'                    => $theme->get( 'Author' ),
 				'auto_update'               => in_array( $stylesheet, $auto_updates, true ),
+				'auto_update_indicated'     => $auto_update_indicated,
 				'requires'                  => $requires,
 				'requires_php'              => $requires_php,
 				'update_unavailable_reason' => isset( $update_unavailable_reason ) ? $update_unavailable_reason : '',