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diff -up openssh-8.6p1/log.c.log-in-chroot openssh-8.6p1/log.c
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--- openssh-8.6p1/log.c.log-in-chroot	2021-04-16 05:55:25.000000000 +0200
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+++ openssh-8.6p1/log.c	2021-05-06 11:32:25.179006811 +0200
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@@ -194,6 +194,11 @@ void
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 log_init(const char *av0, LogLevel level, SyslogFacility facility,
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     int on_stderr)
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 {
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+	log_init_handler(av0, level, facility, on_stderr, 1);
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+}
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+
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+void
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+log_init_handler(const char *av0, LogLevel level, SyslogFacility facility, int on_stderr, int reset_handler) {
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 #if defined(HAVE_OPENLOG_R) && defined(SYSLOG_DATA_INIT)
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 	struct syslog_data sdata = SYSLOG_DATA_INIT;
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 #endif
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@@ -206,8 +211,10 @@ log_init(const char *av0, LogLevel level
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 		exit(1);
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 	}
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-	log_handler = NULL;
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-	log_handler_ctx = NULL;
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+	if (reset_handler) {
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+		log_handler = NULL;
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+		log_handler_ctx = NULL;
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+	}
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 	log_on_stderr = on_stderr;
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 	if (on_stderr)
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diff -up openssh-8.6p1/log.h.log-in-chroot openssh-8.6p1/log.h
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--- openssh-8.6p1/log.h.log-in-chroot	2021-05-06 11:32:25.179006811 +0200
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+++ openssh-8.6p1/log.h	2021-05-06 11:34:22.349925757 +0200
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@@ -52,6 +52,7 @@ typedef enum {
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 typedef void (log_handler_fn)(LogLevel, int, const char *, void *);
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 void     log_init(const char *, LogLevel, SyslogFacility, int);
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+void     log_init_handler(const char *, LogLevel, SyslogFacility, int, int);
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 LogLevel log_level_get(void);
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 int      log_change_level(LogLevel);
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 int      log_is_on_stderr(void);
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diff -up openssh-8.6p1/monitor.c.log-in-chroot openssh-8.6p1/monitor.c
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--- openssh-8.6p1/monitor.c.log-in-chroot	2021-05-06 11:32:25.153006607 +0200
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+++ openssh-8.6p1/monitor.c	2021-05-06 11:33:37.671575348 +0200
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@@ -297,6 +297,8 @@ monitor_child_preauth(struct ssh *ssh, s
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 		close(pmonitor->m_log_sendfd);
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 	pmonitor->m_log_sendfd = pmonitor->m_recvfd = -1;
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+	pmonitor->m_state = "preauth";
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+
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 	authctxt = (Authctxt *)ssh->authctxt;
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 	memset(authctxt, 0, sizeof(*authctxt));
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 	ssh->authctxt = authctxt;
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@@ -408,6 +410,8 @@ monitor_child_postauth(struct ssh *ssh,
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 	close(pmonitor->m_recvfd);
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 	pmonitor->m_recvfd = -1;
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+	pmonitor->m_state = "postauth";
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+
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 	monitor_set_child_handler(pmonitor->m_pid);
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 	ssh_signal(SIGHUP, &monitor_child_handler);
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 	ssh_signal(SIGTERM, &monitor_child_handler);
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@@ -480,7 +484,7 @@ monitor_read_log(struct monitor *pmonito
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 	/* Log it */
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 	if (log_level_name(level) == NULL)
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 		fatal_f("invalid log level %u (corrupted message?)", level);
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-	sshlogdirect(level, forced, "%s [preauth]", msg);
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+	sshlogdirect(level, forced, "%s [%s]", msg, pmonitor->m_state);
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 	sshbuf_free(logmsg);
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 	free(msg);
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@@ -1868,13 +1872,28 @@ monitor_init(void)
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 	mon = xcalloc(1, sizeof(*mon));
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 	monitor_openfds(mon, 1);
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+	mon->m_state = "";
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+
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 	return mon;
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 }
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 void
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-monitor_reinit(struct monitor *mon)
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+monitor_reinit(struct monitor *mon, const char *chroot_dir)
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 {
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-	monitor_openfds(mon, 0);
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+	struct stat dev_log_stat;
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+	char *dev_log_path;
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+	int do_logfds = 0;
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+
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+	if (chroot_dir != NULL) {
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+		xasprintf(&dev_log_path, "%s/dev/log", chroot_dir);
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+
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+		if (stat(dev_log_path, &dev_log_stat) != 0) {
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+			debug_f("/dev/log doesn't exist in %s chroot - will try to log via monitor using [postauth] suffix", chroot_dir);
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+			do_logfds = 1;
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+		}
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+		free(dev_log_path);
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+	}
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+	monitor_openfds(mon, do_logfds);
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 }
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 #ifdef GSSAPI
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diff -up openssh-8.6p1/monitor.h.log-in-chroot openssh-8.6p1/monitor.h
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--- openssh-8.6p1/monitor.h.log-in-chroot	2021-05-06 11:32:25.153006607 +0200
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+++ openssh-8.6p1/monitor.h	2021-05-06 11:32:25.180006819 +0200
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@@ -80,10 +80,11 @@ struct monitor {
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 	int			 m_log_sendfd;
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 	struct kex		**m_pkex;
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 	pid_t			 m_pid;
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+	char		*m_state;
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 };
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9070b3
 struct monitor *monitor_init(void);
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-void monitor_reinit(struct monitor *);
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+void monitor_reinit(struct monitor *, const char *);
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9070b3
 struct Authctxt;
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 void monitor_child_preauth(struct ssh *, struct monitor *);
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diff -up openssh-8.6p1/session.c.log-in-chroot openssh-8.6p1/session.c
9070b3
--- openssh-8.6p1/session.c.log-in-chroot	2021-05-06 11:32:25.166006709 +0200
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+++ openssh-8.6p1/session.c	2021-05-06 11:32:25.181006827 +0200
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@@ -160,6 +160,7 @@ login_cap_t *lc;
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 static int is_child = 0;
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 static int in_chroot = 0;
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+static int have_dev_log = 1;
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 /* File containing userauth info, if ExposeAuthInfo set */
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 static char *auth_info_file = NULL;
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@@ -661,6 +662,7 @@ do_exec(struct ssh *ssh, Session *s, con
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 	int ret;
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 	const char *forced = NULL, *tty = NULL;
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 	char session_type[1024];
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+	struct stat dev_log_stat;
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9070b3
 	if (options.adm_forced_command) {
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 		original_command = command;
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@@ -720,6 +722,10 @@ do_exec(struct ssh *ssh, Session *s, con
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 			tty += 5;
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 	}
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+	if (lstat("/dev/log", &dev_log_stat) != 0) {
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+		have_dev_log = 0;
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+	}
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+
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 	verbose("Starting session: %s%s%s for %s from %.200s port %d id %d",
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 	    session_type,
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 	    tty == NULL ? "" : " on ",
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@@ -1524,14 +1530,6 @@ child_close_fds(struct ssh *ssh)
9070b3
 
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 	/* Stop directing logs to a high-numbered fd before we close it */
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 	log_redirect_stderr_to(NULL);
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-
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-	/*
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-	 * Close any extra open file descriptors so that we don't have them
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-	 * hanging around in clients.  Note that we want to do this after
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-	 * initgroups, because at least on Solaris 2.3 it leaves file
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-	 * descriptors open.
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-	 */
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-	closefrom(STDERR_FILENO + 1);
9070b3
 }
9070b3
 
9070b3
 /*
9070b3
@@ -1665,8 +1663,6 @@ do_child(struct ssh *ssh, Session *s, co
9070b3
 			exit(1);
9070b3
 	}
9070b3
 
9070b3
-	closefrom(STDERR_FILENO + 1);
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-
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 	do_rc_files(ssh, s, shell);
9070b3
 
9070b3
 	/* restore SIGPIPE for child */
9070b3
@@ -1691,9 +1687,17 @@ do_child(struct ssh *ssh, Session *s, co
9070b3
 		argv[i] = NULL;
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 		optind = optreset = 1;
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 		__progname = argv[0];
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-		exit(sftp_server_main(i, argv, s->pw));
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+		exit(sftp_server_main(i, argv, s->pw, have_dev_log));
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 	}
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9070b3
+	/*
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+	 * Close any extra open file descriptors so that we don't have them
9070b3
+	 * hanging around in clients.  Note that we want to do this after
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+	 * initgroups, because at least on Solaris 2.3 it leaves file
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+	 * descriptors open.
9070b3
+	 */
9070b3
+	closefrom(STDERR_FILENO + 1);
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+
9070b3
 	fflush(NULL);
9070b3
 
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 	/* Get the last component of the shell name. */
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diff -up openssh-8.6p1/sftp.h.log-in-chroot openssh-8.6p1/sftp.h
9070b3
--- openssh-8.6p1/sftp.h.log-in-chroot	2021-04-16 05:55:25.000000000 +0200
9070b3
+++ openssh-8.6p1/sftp.h	2021-05-06 11:32:25.181006827 +0200
9070b3
@@ -97,5 +97,5 @@
9070b3
 
9070b3
 struct passwd;
9070b3
 
9070b3
-int	sftp_server_main(int, char **, struct passwd *);
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+int	sftp_server_main(int, char **, struct passwd *, int);
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 void	sftp_server_cleanup_exit(int) __attribute__((noreturn));
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diff -up openssh-8.6p1/sftp-server.c.log-in-chroot openssh-8.6p1/sftp-server.c
9070b3
--- openssh-8.6p1/sftp-server.c.log-in-chroot	2021-04-16 05:55:25.000000000 +0200
9070b3
+++ openssh-8.6p1/sftp-server.c	2021-05-06 11:32:25.181006827 +0200
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@@ -1644,7 +1644,7 @@ sftp_server_usage(void)
9070b3
 }
9070b3
 
9070b3
 int
9070b3
-sftp_server_main(int argc, char **argv, struct passwd *user_pw)
9070b3
+sftp_server_main(int argc, char **argv, struct passwd *user_pw, int reset_handler)
9070b3
 {
9070b3
 	fd_set *rset, *wset;
9070b3
 	int i, r, in, out, max, ch, skipargs = 0, log_stderr = 0;
9070b3
@@ -1657,7 +1657,7 @@ sftp_server_main(int argc, char **argv,
9070b3
 	extern char *__progname;
9070b3
 
9070b3
 	__progname = ssh_get_progname(argv[0]);
9070b3
-	log_init(__progname, log_level, log_facility, log_stderr);
9070b3
+	log_init_handler(__progname, log_level, log_facility, log_stderr, reset_handler);
9070b3
 
9070b3
 	pw = pwcopy(user_pw);
9070b3
 
9070b3
@@ -1730,7 +1730,7 @@ sftp_server_main(int argc, char **argv,
9070b3
 		}
9070b3
 	}
9070b3
 
9070b3
-	log_init(__progname, log_level, log_facility, log_stderr);
9070b3
+	log_init_handler(__progname, log_level, log_facility, log_stderr, reset_handler);
9070b3
 
9070b3
 	/*
9070b3
 	 * On platforms where we can, avoid making /proc/self/{mem,maps}
9070b3
diff -up openssh-8.6p1/sftp-server-main.c.log-in-chroot openssh-8.6p1/sftp-server-main.c
9070b3
--- openssh-8.6p1/sftp-server-main.c.log-in-chroot	2021-04-16 05:55:25.000000000 +0200
9070b3
+++ openssh-8.6p1/sftp-server-main.c	2021-05-06 11:32:25.181006827 +0200
9070b3
@@ -50,5 +50,5 @@ main(int argc, char **argv)
9070b3
 		return 1;
9070b3
 	}
9070b3
 
9070b3
-	return (sftp_server_main(argc, argv, user_pw));
9070b3
+	return (sftp_server_main(argc, argv, user_pw, 0));
9070b3
 }
9070b3
diff -up openssh-8.6p1/sshd.c.log-in-chroot openssh-8.6p1/sshd.c
9070b3
--- openssh-8.6p1/sshd.c.log-in-chroot	2021-05-06 11:32:25.177006795 +0200
9070b3
+++ openssh-8.6p1/sshd.c	2021-05-06 11:32:25.182006834 +0200
9070b3
@@ -559,7 +559,7 @@ privsep_postauth(struct ssh *ssh, Authct
9070b3
 	}
9070b3
 
9070b3
 	/* New socket pair */
9070b3
-	monitor_reinit(pmonitor);
9070b3
+	monitor_reinit(pmonitor, options.chroot_directory);
9070b3
 
9070b3
 	pmonitor->m_pid = fork();
9070b3
 	if (pmonitor->m_pid == -1)
9070b3
@@ -578,6 +578,11 @@ privsep_postauth(struct ssh *ssh, Authct
9070b3
 
9070b3
 	close(pmonitor->m_sendfd);
9070b3
 	pmonitor->m_sendfd = -1;
9070b3
+	close(pmonitor->m_log_recvfd);
9070b3
+	pmonitor->m_log_recvfd = -1;
9070b3
+
9070b3
+	if (pmonitor->m_log_sendfd != -1)
9070b3
+		set_log_handler(mm_log_handler, pmonitor);
9070b3
 
9070b3
 	/* Demote the private keys to public keys. */
9070b3
 	demote_sensitive_data();