diff --git a/shell_integration/windows/NCContextMenu/NCClientInterface.cpp b/shell_integration/windows/NCContextMenu/NCClientInterface.cpp
index 380f4e22291b2..4c5d665139aae 100644
--- a/shell_integration/windows/NCContextMenu/NCClientInterface.cpp
+++ b/shell_integration/windows/NCContextMenu/NCClientInterface.cpp
@@ -48,7 +48,10 @@ NCClientInterface::ContextMenuInfo NCClientInterface::FetchInfo(const std::wstri
     ContextMenuInfo info;
     std::wstring response;
     int sleptCount = 0;
-    while (sleptCount < 20) {
+    constexpr auto noReplyTimeout = 20;
+    constexpr auto replyTimeout = 200;
+    bool receivedReplyFromDesktopClient = false;
+    while ((!receivedReplyFromDesktopClient && sleptCount < noReplyTimeout) || (receivedReplyFromDesktopClient && sleptCount < replyTimeout)) {
         if (socket.ReadLine(&response)) {
             if (StringUtil::begins_with(response, wstring(L"REGISTER_PATH:"))) {
                 wstring responsePath = response.substr(14); // length of REGISTER_PATH
@@ -65,6 +68,9 @@ NCClientInterface::ContextMenuInfo NCClientInterface::FetchInfo(const std::wstri
                 if (!StringUtil::extractChunks(response, commandName, flags, title))
                     continue;
                 info.menuItems.push_back({ commandName, flags, title });
+            } else if (StringUtil::begins_with(response, wstring(L"GET_MENU_ITEMS:BEGIN"))) {
+                receivedReplyFromDesktopClient = true;
+                continue;
             } else if (StringUtil::begins_with(response, wstring(L"GET_MENU_ITEMS:END"))) {
                 break; // Stop once we completely received the last sent request
             }
diff --git a/src/gui/socketapi/socketapi.cpp b/src/gui/socketapi/socketapi.cpp
index 47a589b3de8e3..837884bd8a4b6 100644
--- a/src/gui/socketapi/socketapi.cpp
+++ b/src/gui/socketapi/socketapi.cpp
@@ -1330,7 +1330,7 @@ SocketApi::FileData SocketApi::FileData::parentFolder() const
 
 void SocketApi::command_GET_MENU_ITEMS(const QString &argument, OCC::SocketListener *listener)
 {
-    listener->sendMessage(QString("GET_MENU_ITEMS:BEGIN"));
+    listener->sendMessage(QString("GET_MENU_ITEMS:BEGIN"), true);
     const QStringList files = split(argument);
 
     // Find the common sync folder.