diff --git a/configs/samples/cli.conf.sample b/configs/samples/cli.conf.sample
index f6a546ac82..409c23412b 100644
--- a/configs/samples/cli.conf.sample
+++ b/configs/samples/cli.conf.sample
@@ -7,5 +7,21 @@
 ; Any commands listed in this section will get automatically executed
 ; when Asterisk starts as a daemon or foreground process (-c).
 ;
+; Commands with a value of "pre-init" will run just after the logger
+; is initialized but before all other core and module initialization.
+;
+; Commands with a value of "pre-module" will run just after core
+; initialization is done but before module initialization.
+;
+; These two values can be used for things like enabling debugging on
+; specific modules before they're loaded so you can see debug messages
+; generated during their initialization. Of course you can't run
+; commands from modules that haven't loaded yet.
+
+; Commands with a value of "yes" or "fully-booted" will run after all
+; core and module initialization is completed and just before
+; "Asterisk Ready" is printed on the console.
+;
+;core set debug 3 channels.c = pre-init
+;core set debug 3 res_pjsip.so = pre-module
 ;core set verbose 3 = yes
-;core set debug 1 = yes
diff --git a/main/asterisk.c b/main/asterisk.c
index 9b57e097a0..b0f8a14311 100644
--- a/main/asterisk.c
+++ b/main/asterisk.c
@@ -3528,8 +3528,20 @@ static void canary_exit(void)
 	}
 }
 
+enum startup_commands_phase {
+	STARTUP_COMMANDS_PRE_INIT = 0,
+	STARTUP_COMMANDS_PRE_MODULE,
+	STARTUP_COMMANDS_FULLY_BOOTED
+};
+
+static const char *startup_commands_phase_str[] = {
+	"pre-init",
+	"pre-module",
+	"fully-booted,yes,true,y,t,1,on"
+};
+
 /* Execute CLI commands on startup.  Run by main() thread. */
-static void run_startup_commands(void)
+static void run_startup_commands(enum startup_commands_phase phase)
 {
 	int fd;
 	struct ast_config *cfg;
@@ -3549,8 +3561,10 @@ static void run_startup_commands(void)
 	}
 
 	for (v = ast_variable_browse(cfg, "startup_commands"); v; v = v->next) {
-		if (ast_true(v->value))
+		char *value = ast_str_to_lower(ast_strdupa(v->value));
+		if (ast_in_delimited_string(value, startup_commands_phase_str[phase], ',')) {
 			ast_cli_command(fd, v->name);
+		}
 	}
 
 	close(fd);
@@ -4269,6 +4283,8 @@ static void asterisk_daemon(int isroot, const char *runuser, const char *rungrou
 	threadstorage_init();
 
 	check_init(init_logger(), "Logger");
+	run_startup_commands(STARTUP_COMMANDS_PRE_INIT);
+
 	check_init(ast_rtp_engine_init(), "RTP Engine");
 
 	ast_autoservice_init();
@@ -4303,6 +4319,8 @@ static void asterisk_daemon(int isroot, const char *runuser, const char *rungrou
 	check_init(ast_local_init(), "Local Proxy Channel Driver");
 	check_init(ast_refer_init(), "Refer API");
 
+	run_startup_commands(STARTUP_COMMANDS_PRE_MODULE);
+
 	/* We should avoid most config loads before this point as they can't use realtime. */
 	check_init(load_modules(), "Module");
 
@@ -4340,7 +4358,7 @@ static void asterisk_daemon(int isroot, const char *runuser, const char *rungrou
 	ast_cli_register_multiple(cli_asterisk, ARRAY_LEN(cli_asterisk));
 	ast_register_cleanup(main_atexit);
 
-	run_startup_commands();
+	run_startup_commands(STARTUP_COMMANDS_FULLY_BOOTED);
 	ast_sd_notify("READY=1");
 
 	ast_verb(0, COLORIZE_FMT "\n", COLORIZE(COLOR_BRGREEN, 0, "Asterisk Ready."));