diff --git a/php/WP_CLI/Runner.php b/php/WP_CLI/Runner.php
index de6f29c024..485c3eaf9a 100644
--- a/php/WP_CLI/Runner.php
+++ b/php/WP_CLI/Runner.php
@@ -368,7 +368,9 @@ private function run_ssh_command( $ssh ) {
 		);
 
 		passthru( $escaped_command, $exit_code );
-		if ( 0 !== $exit_code ) {
+		if ( 255 === $exit_code ) {
+			WP_CLI::error( 'Cannot connect over SSH using provided configuration.', 255 );
+		} else {
 			exit( $exit_code );
 		}
 	}