diff --git a/cfg.c b/cfg.c
index 1fcbd0d6..2410fbf9 100644
--- a/cfg.c
+++ b/cfg.c
@@ -157,6 +157,9 @@ cfg_default_done(__unused struct cmd_q *cmdq)
 	cfg_finished = 1;
 
 #ifdef TMATE
+	/* We do it this late, this way, CLI options take precedence over cfg file */
+	tmate_load_cli_options();
+
 	tmate_session_start();
 	if (tmate_foreground && cfg_ncauses) {
 		print_cfg_errors();
diff --git a/client.c b/client.c
index ad349972..456fe793 100644
--- a/client.c
+++ b/client.c
@@ -217,37 +217,37 @@ extern const struct cmd_entry cmd_new_session_entry;
 
 /* For foreground mode */
 static int __argc;
-static char **__argv;
+static const char **__argv;
 #endif
 
-static void _run_initial_client_cmd(int argc, char **argv)
+int run_headless_command(int argc, const char **argv, int flags, void (*err_callback)(const char *))
 {
 	struct cmd_q *cmd_q;
 	struct cmd_list *cmdlist;
 	char *cause;
-	const char *default_argv[] = {"new-session"};
-
-	if (argc == 0) {
-		argc = 1;
-		argv = (char **)default_argv;
-	}
-
 	cmd_q = cmdq_new(NULL); /* No client */
 
 	if ((cmdlist = cmd_list_parse(argc, (char **)argv, NULL, 0, &cause)) == NULL) {
-		tmate_fatal("%s", cause);
+		if (err_callback)
+			err_callback(cause);
+		return -1;
 	}
 
 	cmdq_run(cmd_q, cmdlist, NULL);
 	cmd_list_free(cmdlist);
 	cmdq_free(cmd_q);
 
+	if (flags & DEFER_ERRORS_CFG)
+		return 0;
+
 	/* error messages land in cfg_causes */
 	extern char		**cfg_causes;
 	extern u_int		  cfg_ncauses;
-	int has_error = !!cfg_ncauses;
+
+	int ret = cfg_ncauses ? -1 : 0;
 	for (u_int i = 0; i < cfg_ncauses; i++) {
-		tmate_info("%s", cfg_causes[i]);
+		if (err_callback)
+			err_callback(cfg_causes[i]);
 		free(cfg_causes[i]);
 	}
 
@@ -255,13 +255,27 @@ static void _run_initial_client_cmd(int argc, char **argv)
 	cfg_causes = NULL;
 	cfg_ncauses = 0;
 
-	if (has_error)
-		exit(1);
+	return ret;
+}
+
+static void initial_client_cmd_err_callback(const char *cause)
+{
+	tmate_info("%s", cause);
 }
 
 void run_initial_client_cmd(void)
 {
-	_run_initial_client_cmd(__argc, __argv);
+	int argc = __argc;
+	const char **argv = __argv;
+
+	const char *default_argv[] = {"new-session"};
+	if (argc == 0) {
+		argc = 1;
+		argv = default_argv;
+	}
+
+	if (run_headless_command(argc, argv, 0, initial_client_cmd_err_callback) < 0)
+		exit(1);
 }
 
 /* Client main loop. */
@@ -282,7 +296,7 @@ client_main(struct event_base *base, int argc, char **argv, int flags,
 #ifdef TMATE
 	int cant_nest = 0;
 	__argc = argc;
-	__argv = argv;
+	__argv = (const char **)argv;
 #endif
 
 	/* Ignore SIGCHLD now or daemon() in the server will leave a zombie. */
diff --git a/server.c b/server.c
index f8f08d12..05706769 100644
--- a/server.c
+++ b/server.c
@@ -203,7 +203,6 @@ server_start(struct event_base *base, int lockfd, char *lockfile)
 
 #ifdef TMATE
 	tmate_set_editor_mode();
-	tmate_init_boot_options();
 #endif
 	start_cfg();
 
diff --git a/tmux.c b/tmux.c
index 90b46403..2c790eca 100644
--- a/tmux.c
+++ b/tmux.c
@@ -207,26 +207,20 @@ static char *session_name;
 static char *session_name_ro;
 static char *authorized_keys;
 
-void tmate_init_boot_options(void)
+void tmate_load_cli_options(void)
 {
-	if (account_key)
-		tmate_exec_cmd_args(4, (const char *[]){"set-option", "-g", "tmate-account-key", account_key});
-	if (session_name)
-		tmate_exec_cmd_args(4, (const char *[]){"set-option", "-g", "tmate-session-name", session_name});
-	if (session_name_ro)
-		tmate_exec_cmd_args(4, (const char *[]){"set-option", "-g", "tmate-session-name-ro", session_name_ro});
-	if (authorized_keys)
-		tmate_exec_cmd_args(4, (const char *[]){"set-option", "-g", "tmate-authorized-keys", authorized_keys});
-
-	free(account_key);
-	free(session_name);
-	free(session_name_ro);
-	free(authorized_keys_file);
-
-	account_key = NULL;
-	session_name = NULL;
-	session_name_ro = NULL;
-	authorized_keys = NULL;
+#define SET_OPT(name, val) ({\
+	if (val) { \
+		run_headless_command(3, (const char *[]){"set-option", name, val}, DEFER_ERRORS_CFG, NULL); \
+		free(val); \
+		val = NULL; \
+	} \
+})
+	SET_OPT("tmate-account-key",     account_key);
+	SET_OPT("tmate-account-name",    session_name);
+	SET_OPT("tmate-account-name-ro", session_name_ro);
+	SET_OPT("tmate-authorized-keys", authorized_keys);
+#undef SET_OPT
 }
 #endif
 
diff --git a/tmux.h b/tmux.h
index 83a573c1..9f3ca7bd 100644
--- a/tmux.h
+++ b/tmux.h
@@ -1551,7 +1551,7 @@ extern struct timeval	 start_time;
 extern const char	*socket_path;
 #ifdef TMATE
 extern int tmate_foreground;
-void tmate_init_boot_options(void);
+void tmate_load_cli_options(void);
 #endif
 const char	*getshell(void);
 int		 checkshell(const char *);
@@ -1879,6 +1879,8 @@ void signal_waiting_clients(const char *name);
 void	cmd_wait_for_flush(void);
 
 /* client.c */
+#define DEFER_ERRORS_CFG 1
+int run_headless_command(int argc, const char **argv, int flags, void (*err_callback)(const char *));
 void run_initial_client_cmd(void);
 int	client_main(struct event_base *, int, char **, int, const char *);