diff --git a/composer.json b/composer.json
index 7fe0c9ca1..641f46015 100644
--- a/composer.json
+++ b/composer.json
@@ -24,7 +24,10 @@
     },
     "config": {
         "process-timeout": 7200,
-        "sort-packages": true
+        "sort-packages": true,
+        "allow-plugins": {
+            "dealerdirect/phpcodesniffer-composer-installer": true
+        }
     },
     "extra": {
         "branch-alias": {
diff --git a/features/menu-item.feature b/features/menu-item.feature
index 01da75572..6aa1d33ae 100644
--- a/features/menu-item.feature
+++ b/features/menu-item.feature
@@ -34,10 +34,10 @@ Feature: Manage WordPress menu items
     When I run `wp menu item add-term sidebar-menu post_tag {TERM_ID} --porcelain`
     Then save STDOUT as {TERM_ITEM_ID}
 
-    When I run `wp menu item add-custom sidebar-menu Apple http://apple.com --parent-id={POST_ITEM_ID} --porcelain`
+    When I run `wp menu item add-custom sidebar-menu Apple https://apple.com --parent-id={POST_ITEM_ID} --porcelain`
     Then save STDOUT as {CUSTOM_ITEM_ID}
 
-    When I run `wp menu item update {CUSTOM_ITEM_ID} --title=WordPress --link='http://wordpress.org' --target=_blank --position=2`
+    When I run `wp menu item update {CUSTOM_ITEM_ID} --title=WordPress --link='https://wordpress.org' --target=_blank --position=2`
     Then STDOUT should be:
       """
       Success: Menu item updated.
@@ -51,10 +51,10 @@ Feature: Manage WordPress menu items
 
     When I run `wp menu item list sidebar-menu --fields=type,title,description,position,link,menu_item_parent`
     Then STDOUT should be a table containing rows:
-      | type      | title            | description       | position | link                 | menu_item_parent |
-      | post_type | Custom Test Post | Washington Apples | 1        | {POST_LINK}          | 0                |
-      | custom    | WordPress        |                   | 2        | http://wordpress.org | {POST_ITEM_ID}   |
-      | taxonomy  | Test term        |                   | 3        | {TERM_LINK}          | 0                |
+      | type      | title            | description       | position | link                  | menu_item_parent |
+      | post_type | Custom Test Post | Washington Apples | 1        | {POST_LINK}           | 0                |
+      | custom    | WordPress        |                   | 2        | https://wordpress.org | {POST_ITEM_ID}   |
+      | taxonomy  | Test term        |                   | 3        | {TERM_LINK}           | 0                |
 
     When I run `wp menu item list sidebar-menu --format=ids`
     Then STDOUT should not be empty
@@ -122,7 +122,7 @@ Feature: Manage WordPress menu items
       """
     And the return code should be 1
 
-    When I run `wp menu item add-custom sidebar-menu Apple http://apple.com --porcelain`
+    When I run `wp menu item add-custom sidebar-menu Apple https://apple.com --porcelain`
     Then save STDOUT as {CUSTOM_ITEM_ID}
 
     When I try `wp menu item delete {CUSTOM_ITEM_ID} 99999999`
@@ -132,3 +132,66 @@ Feature: Manage WordPress menu items
       Error: Only deleted 1 of 2 menu items.
       """
     And the return code should be 1
+
+  Scenario: Menu order is recalculated on insertion
+    When I run `wp menu create "Sidebar Menu"`
+    Then STDOUT should not be empty
+
+    When I run `wp menu item add-custom sidebar-menu First https://first.com --porcelain`
+    Then save STDOUT as {ITEM_ID_1}
+
+    When I run `wp menu item add-custom sidebar-menu Second https://second.com --porcelain`
+    Then save STDOUT as {ITEM_ID_2}
+
+    When I run `wp menu item add-custom sidebar-menu Third https://third.com --porcelain`
+    Then save STDOUT as {ITEM_ID_3}
+
+    When I run `wp menu item list sidebar-menu --fields=type,title,position,link`
+    Then STDOUT should be a table containing rows:
+      | type   | title  | position | link               |
+      | custom | First  | 1        | https://first.com  |
+      | custom | Second | 2        | https://second.com |
+      | custom | Third  | 3        | https://third.com  |
+
+    When I run `wp menu item add-custom sidebar-menu Fourth https://fourth.com --position=2 --porcelain`
+    Then save STDOUT as {ITEM_ID_4}
+
+    When I run `wp menu item list sidebar-menu --fields=type,title,position,link`
+    Then STDOUT should be a table containing rows:
+      | type   | title  | position | link               |
+      | custom | First  | 1        | https://first.com  |
+      | custom | Fourth | 2        | https://fourth.com |
+      | custom | Second | 3        | https://second.com |
+      | custom | Third  | 4        | https://third.com  |
+
+  Scenario: Menu order is recalculated on deletion
+    When I run `wp menu create "Sidebar Menu"`
+    Then STDOUT should not be empty
+
+    When I run `wp menu item add-custom sidebar-menu First https://first.com --porcelain`
+    Then save STDOUT as {ITEM_ID_1}
+
+    When I run `wp menu item add-custom sidebar-menu Second https://second.com --porcelain`
+    Then save STDOUT as {ITEM_ID_2}
+
+    When I run `wp menu item add-custom sidebar-menu Third https://third.com --porcelain`
+    Then save STDOUT as {ITEM_ID_3}
+
+    When I run `wp menu item list sidebar-menu --fields=type,title,position,link`
+    Then STDOUT should be a table containing rows:
+      | type   | title  | position | link               |
+      | custom | First  | 1        | https://first.com  |
+      | custom | Second | 2        | https://second.com |
+      | custom | Third  | 3        | https://third.com  |
+
+    When I run `wp menu item delete {ITEM_ID_2}`
+    Then STDOUT should be:
+      """
+      Success: Deleted 1 of 1 menu items.
+      """
+
+    When I run `wp menu item list sidebar-menu --fields=type,title,position,link`
+    Then STDOUT should be a table containing rows:
+      | type   | title  | position | link               |
+      | custom | First  | 1        | https://first.com  |
+      | custom | Third  | 2        | https://third.com  |
diff --git a/src/Menu_Item_Command.php b/src/Menu_Item_Command.php
index 4f4cdeba9..75ee1ce33 100644
--- a/src/Menu_Item_Command.php
+++ b/src/Menu_Item_Command.php
@@ -369,19 +369,28 @@ public function delete( $args, $assoc_args ) {
 
 		foreach ( $args as $arg ) {
 
+			$post           = get_post( $arg );
+			$menu_term      = get_the_terms( $arg, 'nav_menu' );
 			$parent_menu_id = (int) get_post_meta( $arg, '_menu_item_menu_item_parent', true );
 			$result         = wp_delete_post( $arg, true );
 			if ( ! $result ) {
 				WP_CLI::warning( "Couldn't delete menu item {$arg}." );
 				$errors++;
-			} elseif ( $parent_menu_id ) {
-				$children = $wpdb->get_results( $wpdb->prepare( "SELECT post_id FROM $wpdb->postmeta WHERE meta_key='_menu_item_menu_item_parent' AND meta_value=%s", (int) $arg ) );
-				if ( $children ) {
-					$children_query = $wpdb->prepare( "UPDATE $wpdb->postmeta SET meta_value = %d WHERE meta_key = '_menu_item_menu_item_parent' AND meta_value=%s", $parent_menu_id, (int) $arg );
-					// phpcs:ignore WordPress.DB.PreparedSQL.NotPrepared -- $children_query is already prepared above.
-					$wpdb->query( $children_query );
-					foreach ( $children as $child ) {
-						clean_post_cache( $child );
+			} else {
+
+				if ( is_array( $menu_term ) && ! empty( $menu_term ) && $post ) {
+					$this->reorder_menu_items( $menu_term[0]->term_id, $post->menu_order, -1, 0 );
+				}
+
+				if ( $parent_menu_id ) {
+					$children = $wpdb->get_results( $wpdb->prepare( "SELECT post_id FROM $wpdb->postmeta WHERE meta_key='_menu_item_menu_item_parent' AND meta_value=%s", (int) $arg ) );
+					if ( $children ) {
+						$children_query = $wpdb->prepare( "UPDATE $wpdb->postmeta SET meta_value = %d WHERE meta_key = '_menu_item_menu_item_parent' AND meta_value=%s", $parent_menu_id, (int) $arg );
+						// phpcs:ignore WordPress.DB.PreparedSQL.NotPrepared -- $children_query is already prepared above.
+						$wpdb->query( $children_query );
+						foreach ( $children as $child ) {
+							clean_post_cache( $child );
+						}
 					}
 				}
 			}
@@ -477,6 +486,10 @@ private function add_or_update_item( $method, $type, $args, $assoc_args ) {
 			}
 		} else {
 
+			if ( ( 'add' === $method ) && $menu_item_args['menu-item-position'] ) {
+				$this->reorder_menu_items( $menu->term_id, $menu_item_args['menu-item-position'], +1, $result );
+			}
+
 			/**
 			 * Set the menu
 			 *
@@ -503,6 +516,21 @@ private function add_or_update_item( $method, $type, $args, $assoc_args ) {
 
 	}
 
+	/**
+	 * Move block of items in one nav_menu up or down by incrementing/decrementing their menu_order field.
+	 * Expects the menu items to have proper menu_orders (i.e. doesn't fix errors from previous incorrect operations).
+	 *
+	 * @param int $menu_id ID of the nav_menu
+	 * @param int $min_position minimal menu_order to touch
+	 * @param int $increment how much to change menu_order: +1 to move down, -1 to move up
+	 * @param int $ignore_item_id menu item that should be ignored by the change (e.g. newly created menu item)
+	 * @return int number of rows affected
+	 */
+	private function reorder_menu_items( $menu_id, $min_position, $increment, $ignore_item_id = 0 ) {
+		global $wpdb;
+		return $wpdb->query( $wpdb->prepare( "UPDATE $wpdb->posts SET `menu_order`=`menu_order`+(%d) WHERE `menu_order`>=%d AND ID IN (SELECT object_id FROM $wpdb->term_relationships WHERE term_taxonomy_id=%d) AND ID<>%d", (int) $increment, (int) $min_position, (int) $menu_id, (int) $ignore_item_id ) );
+	}
+
 	protected function get_formatter( &$assoc_args ) {
 		return new Formatter( $assoc_args, $this->obj_fields );
 	}