diff --git a/doc/openocd.texi b/doc/openocd.texi
index 4bec637f3..e418e0500 100644
--- a/doc/openocd.texi
+++ b/doc/openocd.texi
@@ -6486,8 +6486,10 @@ Useful in connection with script files
 (@command{script} command and @command{target_name} configuration).
 @end deffn
 
-@deffn Command shutdown
-Close the OpenOCD daemon, disconnecting all clients (GDB, telnet, other).
+@deffn Command shutdown [@option{error}]
+Close the OpenOCD daemon, disconnecting all clients (GDB, telnet,
+other). If option @option{error} is used, OpenOCD will return a
+non-zero exit code to the parent process.
 @end deffn
 
 @anchor{debuglevel}
diff --git a/src/flash/startup.tcl b/src/flash/startup.tcl
index 7a96a3e3b..fbb8d8ee4 100644
--- a/src/flash/startup.tcl
+++ b/src/flash/startup.tcl
@@ -8,8 +8,8 @@
 
 proc program_error {description exit} {
 	if {$exit == 1} {
-	        echo $description
-		shutdown
+		echo $description
+		shutdown error
 	}
 
 	error $description
diff --git a/src/helper/command.c b/src/helper/command.c
index 9d19cff4f..a0aa9e857 100644
--- a/src/helper/command.c
+++ b/src/helper/command.c
@@ -121,7 +121,7 @@ static int command_retval_set(Jim_Interp *interp, int retval)
 	if (return_retval != NULL)
 		*return_retval = retval;
 
-	return (retval == ERROR_OK) ? JIM_OK : JIM_ERR;
+	return (retval == ERROR_OK) ? JIM_OK : retval;
 }
 
 extern struct command_context *global_cmd_ctx;
@@ -659,24 +659,7 @@ int command_run_line(struct command_context *context, char *line)
 		}
 		Jim_DeleteAssocData(interp, "context");
 	}
-	if (retcode == JIM_ERR) {
-		if (retval == ERROR_COMMAND_CLOSE_CONNECTION) {
-			/* Shutdown request is not an error */
-			return ERROR_OK;
-		} else {
-			/* We do not print the connection closed error message */
-			Jim_MakeErrorMessage(interp);
-			LOG_USER("%s", Jim_GetString(Jim_GetResult(interp), NULL));
-		}
-		if (retval == ERROR_OK) {
-			/* It wasn't a low level OpenOCD command that failed */
-			return ERROR_FAIL;
-		}
-		return retval;
-	} else if (retcode == JIM_EXIT) {
-		/* ignore.
-		 * exit(Jim_GetExitCode(interp)); */
-	} else {
+	if (retcode == JIM_OK) {
 		const char *result;
 		int reslen;
 
@@ -696,7 +679,22 @@ int command_run_line(struct command_context *context, char *line)
 			LOG_USER_N("\n");
 		}
 		retval = ERROR_OK;
+	} else if (retcode == JIM_EXIT) {
+		/* ignore.
+		 * exit(Jim_GetExitCode(interp)); */
+	} else if (retcode == ERROR_COMMAND_CLOSE_CONNECTION) {
+		return retcode;
+	} else {
+		Jim_MakeErrorMessage(interp);
+		LOG_USER("%s", Jim_GetString(Jim_GetResult(interp), NULL));
+
+		if (retval == ERROR_OK) {
+			/* It wasn't a low level OpenOCD command that failed */
+			return ERROR_FAIL;
+		}
+		return retval;
 	}
+
 	return retval;
 }
 
diff --git a/src/helper/startup.tcl b/src/helper/startup.tcl
index 926d26b63..4ca2cabc2 100644
--- a/src/helper/startup.tcl
+++ b/src/helper/startup.tcl
@@ -16,10 +16,12 @@ proc exit {} {
 proc ocd_bouncer {name args} {
 	set cmd [format "ocd_%s" $name]
 	set type [eval ocd_command type $cmd $args]
+	set errcode error
 	if {$type == "native"} {
 		return [eval $cmd $args]
 	} else {if {$type == "simple"} {
-		if {[catch {eval $cmd $args}] == 0} {
+		set errcode [catch {eval $cmd $args}]
+		if {$errcode == 0} {
 			return ""
 		} else {
 			# 'classic' commands output error message as part of progress output
@@ -32,7 +34,7 @@ proc ocd_bouncer {name args} {
 	} else {
 		set errmsg [format "invalid subcommand \"%s\"" $args]
 	}}}
-	return -code error $errmsg
+	return -code $errcode $errmsg
 }
 
 # Try flipping / and \ to find file if the filename does not
diff --git a/src/openocd.c b/src/openocd.c
index b0dd21ab2..4d4dc2c83 100644
--- a/src/openocd.c
+++ b/src/openocd.c
@@ -283,7 +283,9 @@ static int openocd_thread(int argc, char *argv[], struct command_context *cmd_ct
 		return ERROR_FAIL;
 
 	ret = parse_config_file(cmd_ctx);
-	if (ret != ERROR_OK)
+	if (ret == ERROR_COMMAND_CLOSE_CONNECTION)
+		return ERROR_OK;
+	else if (ret != ERROR_OK)
 		return ERROR_FAIL;
 
 	ret = server_init(cmd_ctx);
@@ -296,9 +298,15 @@ static int openocd_thread(int argc, char *argv[], struct command_context *cmd_ct
 			return ERROR_FAIL;
 	}
 
-	server_loop(cmd_ctx);
+	ret = server_loop(cmd_ctx);
 
-	return server_quit();
+	int last_signal = server_quit();
+	if (last_signal != ERROR_OK)
+		return last_signal;
+
+	if (ret != ERROR_OK)
+		return ERROR_FAIL;
+	return ERROR_OK;
 }
 
 /* normally this is the main() function entry, but if OpenOCD is linked
diff --git a/src/server/server.c b/src/server/server.c
index 73d8b5b65..7e90d89fd 100644
--- a/src/server/server.c
+++ b/src/server/server.c
@@ -44,7 +44,8 @@
 
 static struct service *services;
 
-/* shutdown_openocd == 1: exit the main event loop, and quit the debugger */
+/* shutdown_openocd == 1: exit the main event loop, and quit the
+ * debugger; 2: quit with non-zero return code */
 static int shutdown_openocd;
 
 /* store received signal to exit application by killing ourselves */
@@ -499,7 +500,7 @@ int server_loop(struct command_context *command_context)
 #endif
 	}
 
-	return ERROR_OK;
+	return shutdown_openocd != 2 ? ERROR_OK : ERROR_FAIL;
 }
 
 #ifdef _WIN32
@@ -608,6 +609,13 @@ COMMAND_HANDLER(handle_shutdown_command)
 
 	shutdown_openocd = 1;
 
+	if (CMD_ARGC == 1) {
+		if (!strcmp(CMD_ARGV[0], "error")) {
+			shutdown_openocd = 2;
+			return ERROR_FAIL;
+		}
+	}
+
 	return ERROR_COMMAND_CLOSE_CONNECTION;
 }