Created attachment 1608 [details]
suggested patch

ChrootDirectory=none is the same as not specifying ChrootDirectory at all. In both cases, sshd should report when the user's directory can't be cd into. It does that only when chroot_directory is NULL. There is a missing check for "none" in session.c:

                /* Suppress missing homedir warning for chroot case */
#ifdef HAVE_LOGIN_CAP
                r = login_getcapbool(lc, "requirehome", 0);
#endif
                if (r || options.chroot_directory == NULL)
                        fprintf(stderr, "Could not chdir to home "
                            "directory %s: %s\n", pw->pw_dir,
                            strerror(errno));

all other checks with chroot_directory has that "none" part. The patch to fix this is very simple and attached. Tested against 5.2p1.