diff --git a/src/http_server.cpp b/src/http_server.cpp
index 092f73b..e960702 100644
--- a/src/http_server.cpp
+++ b/src/http_server.cpp
@@ -195,12 +195,11 @@ void HttpServer::SendEvent(const std::string &message) {
   }
 }
 
-void HttpServer::WatchForCatalogUpdate(DatabaseInstance &db,
-                                       CatalogState &last_state) {
+bool WasCatalogUpdated(DatabaseInstance &db, Connection &connection,
+                       CatalogState &last_state) {
   bool has_change = false;
-  duckdb::Connection con{db};
-  auto &context = *con.context;
-  con.BeginTransaction();
+  auto &context = *connection.context;
+  connection.BeginTransaction();
 
   const auto &databases = db.GetDatabaseManager().GetDatabases(context);
   std::set<idx_t> db_oids;
@@ -234,20 +233,61 @@ void HttpServer::WatchForCatalogUpdate(DatabaseInstance &db,
     }
   }
 
-  // If there was any change, notify the UI
-  if (has_change) {
-    SendCatalogChangedEvent();
+  connection.Rollback();
+  return has_change;
+}
+
+std::string GetMDToken(Connection &connection) {
+  auto query_res = connection.Query("CALL GET_MD_TOKEN()");
+  if (query_res->HasError()) {
+    query_res->ThrowError();
+    return ""; // unreachable
   }
+
+  auto chunk = query_res->Fetch();
+  return chunk->GetValue(0, 0).GetValue<std::string>();
+}
+
+bool IsMDConnected(Connection &con) {
+  if (!con.context->db->ExtensionIsLoaded("motherduck")) {
+    return false;
+  }
+  auto query_res = con.Query("CALL MD_IS_CONNECTED()");
+  if (query_res->HasError()) {
+    std::cerr << "Error in IsMDConnected: " << query_res->GetError()
+              << std::endl;
+    return false;
+  }
+
+  auto chunk = query_res->Fetch();
+  return chunk->GetValue(0, 0).GetValue<bool>();
 }
 
 void HttpServer::Watch() {
   CatalogState last_state;
+  bool is_md_connected = false;
   while (watcher_should_run) {
     auto db = ddb_instance.lock();
     if (!db) {
       break; // DB went away, nothing to watch
     }
-    WatchForCatalogUpdate(*db, last_state);
+
+    try {
+      duckdb::Connection con{*db};
+      if (WasCatalogUpdated(*db, con, last_state)) {
+        SendCatalogChangedEvent();
+      }
+
+      if (!is_md_connected && IsMDConnected(con)) {
+        is_md_connected = true;
+        SendConnectedEvent(GetMDToken(con));
+      }
+    } catch (std::exception &ex) {
+      // Do not crash with uncaught exception, but quit.
+      std::cerr << "Error in watcher: " << ex.what() << std::endl;
+      std::cerr << "Will now terminate." << std::endl;
+      return;
+    }
     {
       std::unique_lock<std::mutex> lock(watcher_mutex);
       watcher_cv.wait_for(lock,
@@ -313,27 +353,23 @@ void HttpServer::HandleGetLocalToken(const httplib::Request &req,
     return;
   }
 
-  Connection connection(*db);
-  auto query_res = connection.Query("CALL get_md_token()");
-  if (query_res->HasError()) {
+  Connection connection{*db};
+  try {
+    auto token = GetMDToken(connection);
+    res.status = 200;
+    res.set_content(token, "text/plain");
+  } catch (std::exception &ex) {
     if (StringUtil::Contains(
-            query_res->GetError(),
-            "GET_MD_TOKEN will be available after you connect")) {
+            ex.what(), "GET_MD_TOKEN will be available after you connect")) {
       // UI expects an empty response if MD isn't connected
+      res.status = 200;
       res.set_content("", "text/plain");
-      return;
+    } else {
+      res.status = 500;
+      res.set_content("Could not get token: " + std::string(ex.what()),
+                      "text/plain");
     }
-
-    res.status = 500;
-    res.set_content("Could not get token: " + query_res->GetError(),
-                    "text/plain");
-    return;
   }
-
-  auto chunk = query_res->Fetch();
-  auto token = chunk->GetValue(0, 0).GetValue<std::string>();
-  res.status = 200;
-  res.set_content(token, "text/plain");
 }
 
 void HttpServer::HandleGet(const httplib::Request &req,
diff --git a/src/include/http_server.hpp b/src/include/http_server.hpp
index 52d0f60..9706a7f 100644
--- a/src/include/http_server.hpp
+++ b/src/include/http_server.hpp
@@ -80,9 +80,6 @@ private:
   void SetResponseEmptyResult(httplib::Response &res);
   void SetResponseErrorResult(httplib::Response &res, const std::string &error);
 
-  // Watchers
-  void WatchForCatalogUpdate(DatabaseInstance &, CatalogState &last_state);
-
   uint16_t local_port;
   std::string remote_url;
   weak_ptr<DatabaseInstance> ddb_instance;