diff --git a/shell_integration/windows/NCContextMenu/NCClientInterface.cpp b/shell_integration/windows/NCContextMenu/NCClientInterface.cpp
index 864e9950676fe..df54575d93a8f 100644
--- a/shell_integration/windows/NCContextMenu/NCClientInterface.cpp
+++ b/shell_integration/windows/NCContextMenu/NCClientInterface.cpp
@@ -46,8 +46,8 @@ NCClientInterface::ContextMenuInfo NCClientInterface::FetchInfo(const std::wstri
         logger << "error with Connect" << std::endl;
         return {};
     }
-    socket.SendMsg(L"GET_STRINGS:CONTEXT_MENU_TITLE\n");
-    socket.SendMsg((L"GET_MENU_ITEMS:" + files + L"\n").data());
+    socket.SendMsg(L"GET_STRINGS:CONTEXT_MENU_TITLE\n", logger);
+    socket.SendMsg((L"GET_MENU_ITEMS:" + files + L"\n").data(), logger);
 
     ContextMenuInfo info;
     std::wstring response;
@@ -97,7 +97,7 @@ NCClientInterface::ContextMenuInfo NCClientInterface::FetchInfo(const std::wstri
     return info;
 }
 
-void NCClientInterface::SendRequest(const wchar_t *verb, const std::wstring &path)
+void NCClientInterface::SendRequest(const wchar_t *verb, const std::wstring &path, std::ofstream &logger)
 {
     auto pipename = CommunicationSocket::DefaultPipePath();
 
@@ -109,5 +109,5 @@ void NCClientInterface::SendRequest(const wchar_t *verb, const std::wstring &pat
         return;
     }
 
-    socket.SendMsg((verb + (L":" + path + L"\n")).data());
+    socket.SendMsg((verb + (L":" + path + L"\n")).data(), logger);
 }
diff --git a/shell_integration/windows/NCContextMenu/NCClientInterface.h b/shell_integration/windows/NCContextMenu/NCClientInterface.h
index 02dc3cdb6b4ff..c0d145c38c03d 100644
--- a/shell_integration/windows/NCContextMenu/NCClientInterface.h
+++ b/shell_integration/windows/NCContextMenu/NCClientInterface.h
@@ -54,7 +54,7 @@ class NCClientInterface
         std::vector<MenuItem> menuItems;
     };
     static ContextMenuInfo FetchInfo(const std::wstring &files, std::ofstream &logger);
-    static void SendRequest(const wchar_t *verb, const std::wstring &path);
+    static void SendRequest(const wchar_t *verb, const std::wstring &path, std::ofstream &logger);
 };
 
 #endif //ABSTRACTSOCKETHANDLER_H
diff --git a/shell_integration/windows/NCContextMenu/NCContextMenu.cpp b/shell_integration/windows/NCContextMenu/NCContextMenu.cpp
index fc774b30bc8a0..72f91cc347649 100644
--- a/shell_integration/windows/NCContextMenu/NCContextMenu.cpp
+++ b/shell_integration/windows/NCContextMenu/NCContextMenu.cpp
@@ -230,7 +230,7 @@ IFACEMETHODIMP NCContextMenu::InvokeCommand(LPCMINVOKECOMMANDINFO pici)
         return E_FAIL;
     }
 
-    NCClientInterface::SendRequest(command.data(), m_selectedFiles);
+    NCClientInterface::SendRequest(command.data(), m_selectedFiles, m_logger);
     return S_OK;
 }
 
diff --git a/shell_integration/windows/NCOverlays/NCOverlay.cpp b/shell_integration/windows/NCOverlays/NCOverlay.cpp
index a70f38b23248d..9d983b3966041 100644
--- a/shell_integration/windows/NCOverlays/NCOverlay.cpp
+++ b/shell_integration/windows/NCOverlays/NCOverlay.cpp
@@ -35,22 +35,24 @@ namespace {
 
 unique_ptr<RemotePathChecker> s_instance;
 
-RemotePathChecker *getGlobalChecker()
+RemotePathChecker *getGlobalChecker(ofstream &logger)
 {
     // On Vista we'll run into issue #2680 if we try to create the thread+pipe connection
     // on any DllGetClassObject of our registered classes.
     // Work around the issue by creating the static RemotePathChecker only once actually needed.
     static once_flag s_onceFlag;
-    call_once(s_onceFlag, [] { s_instance.reset(new RemotePathChecker); });
+    call_once(s_onceFlag, [&logger] { s_instance.reset(new RemotePathChecker{logger}); });
 
     return s_instance.get();
 }
 
 }
-NCOverlay::NCOverlay(int state) 
+NCOverlay::NCOverlay(int state)
     : _referenceCount(1)
     , _state(state)
 {
+    m_logger.open("c:\\testOverlay.log");
+    m_logger << "hello world" << std::endl;
 }
 
 NCOverlay::~NCOverlay(void)
@@ -120,7 +122,7 @@ IFACEMETHODIMP NCOverlay::GetPriority(int *pPriority)
 
 IFACEMETHODIMP NCOverlay::IsMemberOf(PCWSTR pwszPath, DWORD dwAttrib)
 {
-    RemotePathChecker* checker = getGlobalChecker();
+    RemotePathChecker* checker = getGlobalChecker(m_logger);
     std::shared_ptr<const std::vector<std::wstring>> watchedDirectories = checker->WatchedDirectories();
 
     if (watchedDirectories->empty()) {
diff --git a/shell_integration/windows/NCOverlays/NCOverlay.h b/shell_integration/windows/NCOverlays/NCOverlay.h
index 688a6b0950287..45966c9f51d88 100644
--- a/shell_integration/windows/NCOverlays/NCOverlay.h
+++ b/shell_integration/windows/NCOverlays/NCOverlay.h
@@ -18,12 +18,13 @@
 #pragma once
 
 #include <shlobj.h>
+#include <fstream>
 
 class NCOverlay : public IShellIconOverlayIdentifier
 
 {
 public:
-    NCOverlay(int state);
+    explicit NCOverlay(int state);
 
     IFACEMETHODIMP_(ULONG) AddRef();
     IFACEMETHODIMP GetOverlayInfo(PWSTR pwszIconFile, int cchMax, int *pIndex, DWORD *pdwFlags);
@@ -38,6 +39,7 @@ class NCOverlay : public IShellIconOverlayIdentifier
 private:
     long _referenceCount;
     int _state;
+    std::ofstream m_logger;
 };
 
-#endif
\ No newline at end of file
+#endif
diff --git a/shell_integration/windows/NCUtil/CommunicationSocket.cpp b/shell_integration/windows/NCUtil/CommunicationSocket.cpp
index 6f9cdbb983c63..06232675df089 100644
--- a/shell_integration/windows/NCUtil/CommunicationSocket.cpp
+++ b/shell_integration/windows/NCUtil/CommunicationSocket.cpp
@@ -81,8 +81,10 @@ bool CommunicationSocket::Connect(const std::wstring &pipename)
     return true;
 }
 
-bool CommunicationSocket::SendMsg(const wchar_t* message) const
+bool CommunicationSocket::SendMsg(const wchar_t* message, std::ofstream &logger) const
 {
+    logger << "CommunicationSocket::SendMsg: " << (*message) << std::endl;
+
     auto utf8_msg = StringUtil::toUtf8(message);
 
     DWORD numBytesWritten = 0;
diff --git a/shell_integration/windows/NCUtil/CommunicationSocket.h b/shell_integration/windows/NCUtil/CommunicationSocket.h
index bc55c2d933de2..0b631a849670f 100644
--- a/shell_integration/windows/NCUtil/CommunicationSocket.h
+++ b/shell_integration/windows/NCUtil/CommunicationSocket.h
@@ -21,6 +21,7 @@
 
 #include <string>
 #include <vector>
+#include <fstream>
 #include <WinSock2.h>
 
 class __declspec(dllexport) CommunicationSocket
@@ -34,7 +35,7 @@ class __declspec(dllexport) CommunicationSocket
     bool Connect(const std::wstring& pipename);
     bool Close();
 
-    bool SendMsg(const wchar_t*) const;
+    bool SendMsg(const wchar_t*, std::ofstream &logger) const;
     bool ReadLine(std::wstring*);
 
     HANDLE Event() { return _pipe; }
diff --git a/shell_integration/windows/NCUtil/RemotePathChecker.cpp b/shell_integration/windows/NCUtil/RemotePathChecker.cpp
index 5d004d567d286..e61725dd58b76 100644
--- a/shell_integration/windows/NCUtil/RemotePathChecker.cpp
+++ b/shell_integration/windows/NCUtil/RemotePathChecker.cpp
@@ -30,7 +30,7 @@
 using namespace std;
 
 // This code is run in a thread
-void RemotePathChecker::workerThreadLoop()
+void RemotePathChecker::workerThreadLoop(ofstream &logger)
 {
     auto pipename = CommunicationSocket::DefaultPipePath();
     bool connected = false;
@@ -62,7 +62,7 @@ void RemotePathChecker::workerThreadLoop()
                 lock.unlock();
                 if (!asked.count(filePath)) {
                     asked.insert(filePath);
-                    socket.SendMsg(wstring(L"RETRIEVE_FILE_STATUS:" + filePath + L'\n').data());
+                    socket.SendMsg(wstring(L"RETRIEVE_FILE_STATUS:" + filePath + L'\n').data(), logger);
                 }
                 lock.lock();
             }
@@ -162,12 +162,12 @@ void RemotePathChecker::workerThreadLoop()
 
 
 
-RemotePathChecker::RemotePathChecker()
+RemotePathChecker::RemotePathChecker(ofstream &logger)
     : _stop(false)
     , _watchedDirectories(make_shared<const vector<wstring>>())
     , _connected(false)
     , _newQueries(CreateEvent(nullptr, FALSE, FALSE, nullptr))
-    , _thread([this]{ this->workerThreadLoop(); })
+    , _thread([this, &logger]{ this->workerThreadLoop(logger); })
 {
 }
 
diff --git a/shell_integration/windows/NCUtil/RemotePathChecker.h b/shell_integration/windows/NCUtil/RemotePathChecker.h
index 134138f137244..63afba079f928 100644
--- a/shell_integration/windows/NCUtil/RemotePathChecker.h
+++ b/shell_integration/windows/NCUtil/RemotePathChecker.h
@@ -22,6 +22,7 @@
 #include <memory>
 #include <mutex>
 #include <atomic>
+#include <fstream>
 #include <condition_variable>
 
 #pragma once    
@@ -36,7 +37,7 @@ class RemotePathChecker {
         StateWarning,
         StateNone
     };
-    RemotePathChecker();
+    explicit RemotePathChecker(std::ofstream &logger);
     ~RemotePathChecker();
     std::shared_ptr<const std::vector<std::wstring>> WatchedDirectories() const;
     bool IsMonitoredPath(const wchar_t* filePath, int* state);
@@ -64,7 +65,7 @@ class RemotePathChecker {
     HANDLE _newQueries;
 
     std::thread _thread;
-    void workerThreadLoop();
+    void workerThreadLoop(std::ofstream &logger);
 };
 
-#endif
\ No newline at end of file
+#endif
diff --git a/src/gui/application.cpp b/src/gui/application.cpp
index ab80245bb24e6..98832bf04078a 100644
--- a/src/gui/application.cpp
+++ b/src/gui/application.cpp
@@ -659,8 +659,9 @@ void Application::setupLogging()
         logger->setLogDir(_logDir.isEmpty() ? ConfigFile().logDir() : _logDir);
     }
     logger->setLogExpire(_logExpire > 0 ? _logExpire : ConfigFile().logExpire());
-    logger->setLogFlush(_logFlush || ConfigFile().logFlush());
-    logger->setLogDebug(_logDebug || ConfigFile().logDebug());
+    logger->setLogFlush(true || _logFlush || ConfigFile().logFlush());
+    logger->setLogDebug(true || _logDebug || ConfigFile().logDebug());
+
     if (!logger->isLoggingToFile() && ConfigFile().automaticLogDir()) {
         logger->setupTemporaryFolderLogDir();
     }
diff --git a/src/gui/socketapi/socketapi.cpp b/src/gui/socketapi/socketapi.cpp
index 69cd4127f5f5b..f66867676ed86 100644
--- a/src/gui/socketapi/socketapi.cpp
+++ b/src/gui/socketapi/socketapi.cpp
@@ -1352,7 +1352,7 @@ 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.