diff --git a/src/machine/machine.c b/src/machine/machine.c
index 587c2267b6..7f5f48bd9b 100644
--- a/src/machine/machine.c
+++ b/src/machine/machine.c
@@ -804,8 +804,10 @@ int machine_start_shell(
         /* First try to get an fd for the PTY peer via the new racefree ioctl(), directly. Otherwise go via
          * joining the namespace, because it goes by path */
         pty_fd = pty_open_peer_racefree(ptmx_fd, O_RDWR|O_NOCTTY|O_CLOEXEC);
-        if (ERRNO_IS_NEG_NOT_SUPPORTED(pty_fd))
+        if (ERRNO_IS_NEG_NOT_SUPPORTED(pty_fd)) {
+                log_debug_errno(pty_fd, "Failed to get PTY peer via racefree ioctl() (ptmx_fd=%d). Trying via joining the namespace (ptmx_name=%s): %m", ptmx_fd, ptmx_name);
                 pty_fd = machine_open_terminal(m, ptmx_name, O_RDWR|O_NOCTTY|O_CLOEXEC);
+        }
         if (pty_fd < 0)
                 return log_debug_errno(pty_fd, "Failed to open terminal: %m");