diff --git a/tools/steamclient_loader/win/extra_protection/dllmain.cpp b/tools/steamclient_loader/win/extra_protection/dllmain.cpp
index 1441098a..677771a5 100644
--- a/tools/steamclient_loader/win/extra_protection/dllmain.cpp
+++ b/tools/steamclient_loader/win/extra_protection/dllmain.cpp
@@ -8,6 +8,9 @@
 #include <chrono>
 #include <thread>
 
+#if defined(DEBUG) || defined(_DEBUG)
+    #define STUB_EXTRA_DEBUG
+#endif
 
 static std::mutex dll_unload_mtx{};
 static std::condition_variable dll_unload_cv{};
@@ -29,7 +32,7 @@ static void send_unload_signal()
 DWORD WINAPI self_unload(LPVOID lpParameter)
 {
     constexpr const auto UNLOAD_TIMEOUT =
-#ifdef _DEBUG
+#ifdef STUB_EXTRA_DEBUG
         std::chrono::minutes(5)
 #else
         std::chrono::seconds(5)
@@ -37,8 +40,21 @@ DWORD WINAPI self_unload(LPVOID lpParameter)
     ;
 
     {
+#ifdef STUB_EXTRA_DEBUG
+        auto t1 = std::chrono::high_resolution_clock::now();
+#endif
+
         std::unique_lock lock(dll_unload_mtx);
-        dll_unload_cv.wait_for(lock, UNLOAD_TIMEOUT, [](){ return unload_dll; });
+        dll_unload_cv.wait_for(lock, UNLOAD_TIMEOUT, []{ return unload_dll; });
+        
+#ifdef STUB_EXTRA_DEBUG
+        if (!unload_dll) { // flag was not raised, means we timed out
+            auto t2 = std::chrono::high_resolution_clock::now();
+            auto dd = std::chrono::duration_cast<std::chrono::seconds>(t2 - t1);
+            std::string msg = "Unloading after " + std::to_string(dd.count()) + " seconds, due to timeout";
+            MessageBoxA(nullptr, msg.c_str(), "Self-unload thread", MB_OK | MB_ICONERROR);
+        }
+#endif
     }
     unload_thread_handle = INVALID_HANDLE_VALUE;
     FreeLibraryAndExitThread(my_hModule, 0);
@@ -52,19 +68,27 @@ BOOL APIENTRY DllMain(
     switch (reason)
     {
     case DLL_PROCESS_ATTACH:
+        stubdrm::set_cleanup_cb(send_unload_signal);
+        my_hModule = hModule;
         if (!stubdrm::patch()) {
+#ifdef STUB_EXTRA_DEBUG
+            MessageBoxA(nullptr, "Failed to detect .bind", "Main", MB_OK | MB_ICONERROR);
+#endif
+
             // https://learn.microsoft.com/en-us/windows/win32/dlls/dllmain
             // "The system immediately calls your entry-point function with DLL_PROCESS_DETACH and unloads the DLL"
             unload_dll = true;
             return FALSE;
         }
-        my_hModule = hModule;
-        stubdrm::set_cleanup_cb(send_unload_signal);
         unload_thread_handle = CreateThread(nullptr, 0, self_unload, nullptr, 0, nullptr);
         break;
         
     case DLL_PROCESS_DETACH:
         if (!unload_dll) { // not unloaded yet, just an early exit, or thread timed out
+#ifdef STUB_EXTRA_DEBUG
+            MessageBoxA(nullptr, "Unclean exit", "Main", MB_OK | MB_ICONERROR);
+#endif
+
             stubdrm::restore();
             if (unload_thread_handle != INVALID_HANDLE_VALUE && unload_thread_handle != NULL) {
                 TerminateThread(unload_thread_handle, 0);