diff --git a/include/sway/output.h b/include/sway/output.h
index 70f746dc..8180ce3d 100644
--- a/include/sway/output.h
+++ b/include/sway/output.h
@@ -32,6 +32,10 @@ struct sway_output {
 	struct wl_list link;
 
 	pid_t bg_pid;
+
+	struct {
+		struct wl_signal destroy;
+	} events;
 };
 
 void output_damage_whole(struct sway_output *output);
diff --git a/sway/commands/output/background.c b/sway/commands/output/background.c
index 82bccf68..55cbdff0 100644
--- a/sway/commands/output/background.c
+++ b/sway/commands/output/background.c
@@ -62,46 +62,56 @@ struct cmd_results *output_cmd_background(int argc, char **argv) {
 		wordexp_t p;
 		char *src = join_args(argv, j);
 		if (wordexp(src, &p, 0) != 0 || p.we_wordv[0] == NULL) {
-			return cmd_results_new(CMD_INVALID, "output",
-				"Invalid syntax (%s).", src);
+			struct cmd_results *cmd_res = cmd_results_new(CMD_INVALID, "output",
+				"Invalid syntax (%s)", src);
+			free(src);
+			wordfree(&p);
+			return cmd_res;
 		}
 		free(src);
-		src = p.we_wordv[0];
+		src = strdup(p.we_wordv[0]);
+		wordfree(&p);
+		if (!src) {
+			wlr_log(L_ERROR, "Failed to duplicate string");
+			return cmd_results_new(CMD_FAILURE, "output",
+				"Unable to allocate resource");
+		}
+
 		if (config->reading && *src != '/') {
+			// src file is inside configuration dir
+
 			char *conf = strdup(config->current_config);
-			if (conf) {
-				char *conf_path = dirname(conf);
-				src = malloc(strlen(conf_path) + strlen(src) + 2);
-				if (!src) {
-					free(conf);
-					wordfree(&p);
-					wlr_log(L_ERROR,
-						"Unable to allocate resource: Not enough memory");
-					return cmd_results_new(CMD_FAILURE, "output",
+			if(!conf) {
+				wlr_log(L_ERROR, "Failed to duplicate string");
+				return cmd_results_new(CMD_FAILURE, "output",
 						"Unable to allocate resources");
-				}
-				sprintf(src, "%s/%s", conf_path, p.we_wordv[0]);
-				free(conf);
-			} else {
-				wlr_log(L_ERROR, "Unable to allocate background source");
 			}
+
+			char *conf_path = dirname(conf);
+			char *rel_path = src;
+			src = malloc(strlen(conf_path) + strlen(src) + 2);
+			if (!src) {
+				free(rel_path);
+				free(conf);
+				wlr_log(L_ERROR, "Unable to allocate memory");
+				return cmd_results_new(CMD_FAILURE, "output",
+						"Unable to allocate resources");
+			}
+
+			sprintf(src, "%s/%s", conf_path, rel_path);
+			free(rel_path);
+			free(conf);
 		}
 
 		if (access(src, F_OK) == -1) {
 			struct cmd_results *cmd_res = cmd_results_new(CMD_FAILURE, "output",
 				"Unable to access background file '%s': %s", src, strerror(errno));
 			free(src);
-			wordfree(&p);
 			return cmd_res;
 		}
 
-		output->background = strdup(src);
+		output->background = src;
 		output->background_option = strdup(mode);
-		if (src != p.we_wordv[0]) {
-			free(src);
-		}
-		wordfree(&p);
-
 		argc -= j + 1; argv += j + 1;
 	}
 
diff --git a/sway/desktop/layer_shell.c b/sway/desktop/layer_shell.c
index 3accdefb..b57d1ee6 100644
--- a/sway/desktop/layer_shell.c
+++ b/sway/desktop/layer_shell.c
@@ -219,6 +219,8 @@ static void handle_output_destroy(struct wl_listener *listener, void *data) {
 	struct sway_layer_surface *sway_layer =
 		wl_container_of(listener, sway_layer, output_destroy);
 	wl_list_remove(&sway_layer->output_destroy.link);
+	wl_list_remove(&sway_layer->link);
+	wl_list_init(&sway_layer->link);
 	sway_layer->layer_surface->output = NULL;
 	wlr_layer_surface_close(sway_layer->layer_surface);
 }
@@ -350,10 +352,6 @@ void handle_layer_shell_surface(struct wl_listener *listener, void *data) {
 	wl_signal_add(&layer_surface->surface->events.commit,
 		&sway_layer->surface_commit);
 
-	sway_layer->output_destroy.notify = handle_output_destroy;
-	wl_signal_add(&layer_surface->output->events.destroy,
-		&sway_layer->output_destroy);
-
 	sway_layer->destroy.notify = handle_destroy;
 	wl_signal_add(&layer_surface->events.destroy, &sway_layer->destroy);
 	sway_layer->map.notify = handle_map;
@@ -366,6 +364,9 @@ void handle_layer_shell_surface(struct wl_listener *listener, void *data) {
 	layer_surface->data = sway_layer;
 
 	struct sway_output *output = layer_surface->output->data;
+	sway_layer->output_destroy.notify = handle_output_destroy;
+	wl_signal_add(&output->events.destroy, &sway_layer->output_destroy);
+
 	wl_list_insert(&output->layers[layer_surface->layer], &sway_layer->link);
 
 	// Temporarily set the layer's current state to client_pending
diff --git a/sway/desktop/output.c b/sway/desktop/output.c
index d4115be8..f0f1603a 100644
--- a/sway/desktop/output.c
+++ b/sway/desktop/output.c
@@ -1199,6 +1199,8 @@ static void damage_handle_destroy(struct wl_listener *listener, void *data) {
 
 static void handle_destroy(struct wl_listener *listener, void *data) {
 	struct sway_output *output = wl_container_of(listener, output, destroy);
+	wl_signal_emit(&output->events.destroy, output);
+
 	if (output->swayc) {
 		container_destroy(output->swayc);
 	}
@@ -1277,6 +1279,7 @@ void output_enable(struct sway_output *output) {
 	for (size_t i = 0; i < len; ++i) {
 		wl_list_init(&output->layers[i]);
 	}
+	wl_signal_init(&output->events.destroy);
 
 	input_manager_configure_xcursor(input_manager);