diff --git a/include/plugin.hpp b/include/plugin.hpp
index 29b9aa45..cbe04424 100644
--- a/include/plugin.hpp
+++ b/include/plugin.hpp
@@ -47,7 +47,8 @@ extern std::vector<Plugin*> plugins;
 
 extern std::string loginStatus;
 extern std::vector<Update> updates;
-extern bool updatesFinished;
+extern std::string updateStatus;
+extern bool restartRequested;
 
 
 } // namespace plugin
diff --git a/src/app/MenuBar.cpp b/src/app/MenuBar.cpp
index 009209f8..beda3518 100644
--- a/src/app/MenuBar.cpp
+++ b/src/app/MenuBar.cpp
@@ -497,7 +497,20 @@ struct LogInItem : ui::MenuItem {
 
 struct SyncItem : ui::MenuItem {
 	void step() override {
-		disabled = !plugin::hasUpdates() || plugin::isSyncing();
+		disabled = true;
+		if (plugin::updateStatus != "") {
+			text = plugin::updateStatus;
+		}
+		else if (plugin::isSyncing()) {
+			text = "Updating...";
+		}
+		else if (!plugin::hasUpdates()) {
+			text = "No updates";
+		}
+		else {
+			text = "Update all";
+			disabled = false;
+		}
 		MenuItem::step();
 	}
 
@@ -661,8 +674,8 @@ struct LibraryButton : MenuButton {
 		notification->visible = plugin::hasUpdates();
 
 		// Popup when updates finish downloading
-		if (plugin::updatesFinished) {
-			plugin::updatesFinished = false;
+		if (plugin::restartRequested) {
+			plugin::restartRequested = false;
 			if (osdialog_message(OSDIALOG_INFO, OSDIALOG_OK_CANCEL, "All plugins have been downloaded. Close and re-launch Rack to load new updates.")) {
 				APP->window->close();
 			}
diff --git a/src/plugin.cpp b/src/plugin.cpp
index 293737e2..a1c679ab 100644
--- a/src/plugin.cpp
+++ b/src/plugin.cpp
@@ -351,7 +351,9 @@ bool isLoggedIn() {
 void queryUpdates() {
 	if (settings::token.empty())
 		return;
+
 	updates.clear();
+	updateStatus = "Querying for updates...";
 
 	// Get user's plugins list
 	std::string pluginsUrl = app::API_URL + "/plugins";
@@ -361,6 +363,7 @@ void queryUpdates() {
 	json_decref(pluginsReqJ);
 	if (!pluginsResJ) {
 		WARN("Request for user's plugins failed");
+		updateStatus = "Could not query updates";
 		return;
 	}
 	DEFER({
@@ -370,6 +373,7 @@ void queryUpdates() {
 	json_t *errorJ = json_object_get(pluginsResJ, "error");
 	if (errorJ) {
 		WARN("Request for user's plugins returned an error: %s", json_string_value(errorJ));
+		updateStatus = "Could not query updates";
 		return;
 	}
 
@@ -381,6 +385,7 @@ void queryUpdates() {
 	json_decref(manifestsReq);
 	if (!manifestsResJ) {
 		WARN("Request for library manifests failed");
+		updateStatus = "Could not query updates";
 		return;
 	}
 	DEFER({
@@ -436,6 +441,8 @@ void queryUpdates() {
 
 		updates.push_back(update);
 	}
+
+	updateStatus = "";
 }
 
 bool hasUpdates() {
@@ -492,7 +499,7 @@ void syncUpdates() {
 		if (update.progress < 1.f)
 			syncUpdate(&update);
 	}
-	updatesFinished = true;
+	restartRequested = true;
 }
 
 bool isSyncing() {
@@ -641,7 +648,8 @@ std::vector<Plugin*> plugins;
 
 std::string loginStatus;
 std::vector<Update> updates;
-bool updatesFinished = false;
+std::string updateStatus;
+bool restartRequested = false;
 
 
 } // namespace plugin