diff --git a/features/option.feature b/features/option.feature
index 212f82d4d..d2f52a9bf 100644
--- a/features/option.feature
+++ b/features/option.feature
@@ -180,6 +180,113 @@ Feature: Manage WordPress options
       | option_name  | option_value   | autoload |
       | hello        | island         | on      |
 
+  @require-wp-4.2
+  @less-than-wp-6.6
+  Scenario: Update autoload value for custom option with an unchanged value
+    Given a WP install
+    And I run `wp option add hello world --autoload=yes`
+
+    When I run `wp option update hello world --autoload=no`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      no
+      """
+
+    When I run `wp option update hello world --autoload=yes`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      yes
+      """
+
+    When I run `wp option update hello world --autoload=off`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      no
+      """
+
+    When I run `wp option update hello world --autoload=on`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      yes
+      """
+
+  @require-wp-6.6
+  Scenario: Update autoload value for custom option with an unchanged value
+    Given a WP install
+    And I run `wp option add hello world --autoload=on`
+
+    When I run `wp option update hello world --autoload=off`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      off
+      """
+
+    When I run `wp option update hello world --autoload=on`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      on
+      """
+
+    When I run `wp option update hello world --autoload=no`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      off
+      """
+
+    When I run `wp option update hello world --autoload=yes`
+    Then STDOUT should be:
+      """
+      Success: Updated autoload value for 'hello' option.
+      """
+
+    When I run `wp option get-autoload hello`
+    Then STDOUT should be:
+      """
+      on
+      """
+
   @require-wp-4.2
   @less-than-wp-6.6
   Scenario: Managed autoloaded options
diff --git a/src/Option_Command.php b/src/Option_Command.php
index e4cd076f2..1d4af6d30 100644
--- a/src/Option_Command.php
+++ b/src/Option_Command.php
@@ -454,6 +454,15 @@ public function update( $args, $assoc_args ) {
 
 		if ( $value === $old_value && null === $autoload ) {
 			WP_CLI::success( "Value passed for '{$key}' option is unchanged." );
+		} elseif ( $value === $old_value ) {
+			// Store the value update_option() would: WordPress before 6.6 only autoloads 'yes'.
+			$autoload_on = in_array( $autoload, [ 'on', 'yes' ], true );
+			if ( Utils\wp_version_compare( '6.6', '<' ) ) {
+				$autoload = $autoload_on ? 'yes' : 'no';
+			} else {
+				$autoload = $autoload_on ? 'on' : 'off';
+			}
+			$this->set_autoload( [ $key, $autoload ] );
 			// @phpstan-ignore argument.type
 		} elseif ( update_option( $key, $value, $autoload ) ) {
 				WP_CLI::success( "Updated '{$key}' option." );