diff --git a/includes/api/class-wc-rest-system-status-tools-controller.php b/includes/api/class-wc-rest-system-status-tools-controller.php
index 44b6379b4d1..fcb54c7257a 100644
--- a/includes/api/class-wc-rest-system-status-tools-controller.php
+++ b/includes/api/class-wc-rest-system-status-tools-controller.php
@@ -183,7 +183,7 @@ class WC_REST_System_Status_Tools_Controller extends WC_REST_Controller {
 		);
 
 		// Jetpack does the image resizing heavy lifting so you don't have to.
-		if ( ( class_exists( 'Jetpack' ) && Jetpack::is_module_active( 'photon' ) ) || ! apply_filters( 'woocommerce_background_image_regeneration', ! is_multisite() ) ) {
+		if ( ( class_exists( 'Jetpack' ) && Jetpack::is_module_active( 'photon' ) ) || ! apply_filters( 'woocommerce_background_image_regeneration', true ) ) {
 			unset( $tools['regenerate_thumbnails'] );
 		}
 
diff --git a/includes/class-wc-regenerate-images.php b/includes/class-wc-regenerate-images.php
index d1eb388f571..407e42833f0 100644
--- a/includes/class-wc-regenerate-images.php
+++ b/includes/class-wc-regenerate-images.php
@@ -47,16 +47,19 @@ class WC_Regenerate_Images {
 			return;
 		}
 
-		// Regenerate thumbnails in the background after settings change. Not ran on multisite to avoid multiple simultanious jobs, and not required when Jetpack Photon is in use.
-		if ( apply_filters( 'woocommerce_background_image_regeneration', ! is_multisite() ) ) {
+		if ( apply_filters( 'woocommerce_background_image_regeneration', true ) ) {
 			include_once WC_ABSPATH . 'includes/class-wc-regenerate-images-request.php';
 
 			self::$background_process = new WC_Regenerate_Images_Request();
 
 			add_action( 'admin_init', array( __CLASS__, 'regenerating_notice' ) );
 			add_action( 'woocommerce_hide_regenerating_thumbnails_notice', array( __CLASS__, 'dismiss_regenerating_notice' ) );
-			add_action( 'customize_save_after', array( __CLASS__, 'maybe_regenerate_images' ) );
-			add_action( 'after_switch_theme', array( __CLASS__, 'maybe_regenerate_images' ) );
+
+			// Regenerate thumbnails in the background after settings changes. Not ran on multisite to avoid multiple simultanious jobs.
+			if ( ! is_multisite() ) {
+				add_action( 'customize_save_after', array( __CLASS__, 'maybe_regenerate_images' ) );
+				add_action( 'after_switch_theme', array( __CLASS__, 'maybe_regenerate_images' ) );
+			}
 		}
 	}
 
diff --git a/includes/customizer/class-wc-shop-customizer.php b/includes/customizer/class-wc-shop-customizer.php
index 31c5351ced2..222067bad10 100644
--- a/includes/customizer/class-wc-shop-customizer.php
+++ b/includes/customizer/class-wc-shop-customizer.php
@@ -443,12 +443,23 @@ class WC_Shop_Customizer {
 	 * @param WP_Customize_Manager $wp_customize Theme Customizer object.
 	 */
 	private function add_product_images_section( $wp_customize ) {
+		if ( class_exists( 'Jetpack' ) && Jetpack::is_module_active( 'photon' ) ) {
+			$regen_description = ''; // Nothing to report; Jetpack will handle magically.
+		} elseif ( apply_filters( 'woocommerce_background_image_regeneration', true ) && ! is_multisite() ) {
+			$regen_description = __( 'After publishing your changes, new image sizes will be generated automatically.', 'woocommerce' );
+		} elseif ( apply_filters( 'woocommerce_background_image_regeneration', true ) && is_multisite() ) {
+			$regen_description = sprintf( __( 'After publishing your changes, new image sizes may not be shown until you regenerate thumbnails. You can do this from the <a href="%1$s" target="_blank">tools section in WooCommerce</a> or by using a plugin such as <a href="%2$s" target="_blank">Regenerate Thumbnails</a>.', 'woocommerce' ), admin_url( 'admin.php?page=wc-status&tab=tools' ), 'https://en-gb.wordpress.org/plugins/regenerate-thumbnails/' );
+		} else {
+			$regen_description = sprintf( __( 'After publishing your changes, new image sizes may not be shown until you <a href="%2$s" target="_blank">Regenerate Thumbnails</a>.', 'woocommerce' ), 'https://en-gb.wordpress.org/plugins/regenerate-thumbnails/' );
+		}
+
 		$wp_customize->add_section(
 			'woocommerce_product_images',
 			array(
-				'title'    => __( 'Product Images', 'woocommerce' ),
-				'priority' => 20,
-				'panel'    => 'woocommerce',
+				'title'       => __( 'Product Images', 'woocommerce' ),
+				'description' => $regen_description,
+				'priority'    => 20,
+				'panel'       => 'woocommerce',
 			)
 		);