diff --git a/plugins/woocommerce/includes/abstracts/abstract-wc-product.php b/plugins/woocommerce/includes/abstracts/abstract-wc-product.php
index 3dd5352b356..71ffba8a229 100644
--- a/plugins/woocommerce/includes/abstracts/abstract-wc-product.php
+++ b/plugins/woocommerce/includes/abstracts/abstract-wc-product.php
@@ -1202,7 +1202,7 @@ class WC_Product extends WC_Abstract_Legacy_Product {
 	/**
 	 * Set downloads.
 	 *
-	 * @throws WC_Data_Exception
+	 * @throws WC_Data_Exception If an error relating to one of the downloads is encountered.
 	 *
 	 * @param array $downloads_array Array of WC_Product_Download objects or arrays.
 	 *
diff --git a/plugins/woocommerce/tests/php/includes/class-wc-product-downloads-test.php b/plugins/woocommerce/tests/php/includes/class-wc-product-downloads-test.php
index 0cb0ad4dc15..8192a44a069 100644
--- a/plugins/woocommerce/tests/php/includes/class-wc-product-downloads-test.php
+++ b/plugins/woocommerce/tests/php/includes/class-wc-product-downloads-test.php
@@ -9,7 +9,7 @@ class WC_Product_Download_Test extends WC_Unit_Test_Case {
 	 * Test for file without extension.
 	 */
 	public function test_is_allowed_filetype_with_no_extension() {
-		$upload_dir = trailingslashit( wp_upload_dir()['basedir'] );
+		$upload_dir                  = trailingslashit( wp_upload_dir()['basedir'] );
 		$file_path_with_no_extension = $upload_dir . 'upload_file';
 		if ( ! file_exists( $file_path_with_no_extension ) ) {
 			// Copy an existing file without extension.
@@ -24,7 +24,7 @@ class WC_Product_Download_Test extends WC_Unit_Test_Case {
 	 * Simulates test condition for windows when filename ends with a period.
 	 */
 	public function test_is_allowed_filetype_on_windows_with_period_at_end() {
-		$upload_dir = trailingslashit( wp_upload_dir()['basedir'] );
+		$upload_dir                   = trailingslashit( wp_upload_dir()['basedir'] );
 		$file_path_with_period_at_end = $upload_dir . 'upload_file.';
 		if ( ! file_exists( $file_path_with_period_at_end ) ) {
 			// Copy an existing file without extension.
@@ -45,8 +45,20 @@ class WC_Product_Download_Test extends WC_Unit_Test_Case {
 		$download_directories = wc_get_container()->get( Download_Directories::class );
 		$download_directories->set_mode( Download_Directories::MODE_ENABLED );
 
-		$non_admin_user = wp_insert_user( array( 'user_login' => uniqid(), 'role' => 'editor', 'user_pass' => 'x' ) );
-		$admin_user     = wp_insert_user( array( 'user_login' => uniqid(), 'role' => 'administrator', 'user_pass' => 'x' ) );
+		$non_admin_user = wp_insert_user(
+			array(
+				'user_login' => uniqid(),
+				'role'       => 'editor',
+				'user_pass'  => 'x',
+			)
+		);
+		$admin_user     = wp_insert_user(
+			array(
+				'user_login' => uniqid(),
+				'role'       => 'administrator',
+				'user_pass'  => 'x',
+			)
+		);
 		$ebook_url      = 'https://external.site/books/ultimate-guide-to-stuff.pdf';
 		$podcast_url    = 'https://external.site/podcasts/ultimate-guide-to-stuff.mp3';
 
@@ -63,4 +75,57 @@ class WC_Product_Download_Test extends WC_Unit_Test_Case {
 		$this->expectExceptionMessage( 'cannot be used: it is not located in an approved directory' );
 		$download->check_is_valid();
 	}
+
+	/**
+	 * Test handling of filepaths described via shortcodes in relation to the Approved Download Directory
+	 * feature. This is to simulate scenarios such as encountered when using the S3 Downloads extension.
+	 */
+	public function test_shortcode_resolution_for_approved_directory_rules() {
+		/** @var Download_Directories $download_directories */
+		$download_directories = wc_get_container()->get( Download_Directories::class );
+		$download_directories->set_mode( Download_Directories::MODE_ENABLED );
+		$dynamic_filepath = 'https://fast.reliable.external.fileserver.com/bucket-123/textbook.pdf';
+
+		// We select an admin user because we wish to automatically add Approved Directory rules.
+		$admin_user = wp_insert_user(
+			array(
+				'user_login' => uniqid(),
+				'role'       => 'administrator',
+				'user_pass'  => 'x',
+			)
+		);
+		wp_set_current_user( $admin_user );
+
+		add_shortcode(
+			'dynamic-download',
+			function () {
+				return 'https://fast.reliable.external.fileserver.com/bucket-123/textbook.pdf';
+			}
+		);
+
+		$this->assertFalse(
+			$download_directories->is_valid_path( $dynamic_filepath ),
+			'Confirm the filepath returned by the test URL is not yet valid.'
+		);
+
+		$download = new WC_Product_Download();
+		$download->set_file( '[dynamic-download]' );
+
+		$this->assertNull(
+			$download->check_is_valid(),
+			'The downloadable file successfully validates (if it did not, an exception would be thrown).'
+		);
+
+		$this->assertTrue(
+			$download_directories->is_valid_path( $dynamic_filepath ),
+			'Confirm the filepath returned by the test URL is now considered valid.'
+		);
+
+		remove_shortcode( 'dynamic-download' );
+
+		// Now the shortcode is removed (perhaps the parent plugin has been removed/disabled) it will not resolve
+		// and so the filepath will not validate.
+		$this->expectException( 'Error' );
+		$download_directories->check_is_valid();
+	}
 }