diff --git a/src/shared/mount-util.c b/src/shared/mount-util.c
index ff95fbc569..594efea989 100644
--- a/src/shared/mount-util.c
+++ b/src/shared/mount-util.c
@@ -251,7 +251,13 @@ int bind_remount_recursive_with_mountinfo(
 
                         r = hashmap_ensure_put(&todo, &path_hash_ops_free, d, ULONG_TO_PTR(flags));
                         if (r == -EEXIST)
-                                continue;
+                                /* If the same path was recorded, but with different mount flags, update it:
+                                 * it means a mount point is overmounted, and libmount returns the "bottom" (or
+                                 * older one) first, but we want to reapply the flags from the "top" (or newer
+                                 * one). See: https://github.com/systemd/systemd/issues/20032
+                                 * Note that this shouldn't really fail, as we were just told that the key
+                                 * exists, and it's an update so we want 'd' to be freed immediately. */
+                                r = hashmap_update(todo, d, ULONG_TO_PTR(flags));
                         if (r < 0)
                                 return r;
                         if (r > 0)