diff --git a/cmake/platform/win/settings.cmake b/cmake/platform/win/settings.cmake
index d30d81479a..40d2c578ba 100644
--- a/cmake/platform/win/settings.cmake
+++ b/cmake/platform/win/settings.cmake
@@ -1,4 +1,8 @@
-add_definitions(-D_WIN32_WINNT=0x0601)
+add_definitions(-D_WIN32_WINNT=0x0A00)      # Windows 10
+add_definitions(-DNTDDI_VERSION=0x0A000007) # 19H1 (1903)
+add_definitions(-DWIN32_LEAN_AND_MEAN)
+add_definitions(-DNOMINMAX)
+add_definitions(-DTRINITY_REQUIRED_WINDOWS_BUILD=18362)
 
 if(CMAKE_CXX_COMPILER_ID STREQUAL "MSVC" OR CMAKE_CXX_COMPILER_FRONTEND_VARIANT STREQUAL "MSVC")
   include(${CMAKE_SOURCE_DIR}/cmake/compiler/msvc/settings.cmake)
diff --git a/src/common/Debugging/Errors.cpp b/src/common/Debugging/Errors.cpp
index b00402d5ff..8532906d85 100644
--- a/src/common/Debugging/Errors.cpp
+++ b/src/common/Debugging/Errors.cpp
@@ -129,6 +129,20 @@ void Abort(char const* file, int line, char const* function)
     Crash(formattedMessage.c_str());
 }
 
+void Abort(char const* file, int line, char const* function, char const* message, ...)
+{
+    va_list args;
+    va_start(args, message);
+
+    std::string formattedMessage = StringFormat("\n%s:%i in %s ABORTED:\n", file, line, function) + FormatAssertionMessage(message, args) + '\n';
+    va_end(args);
+
+    fprintf(stderr, "%s", formattedMessage.c_str());
+    fflush(stderr);
+
+    Crash(formattedMessage.c_str());
+}
+
 void AbortHandler(int sigval)
 {
     // nothing useful to log here, no way to pass args
diff --git a/src/common/Debugging/Errors.h b/src/common/Debugging/Errors.h
index 2233f49cd2..bd662eef2d 100644
--- a/src/common/Debugging/Errors.h
+++ b/src/common/Debugging/Errors.h
@@ -30,6 +30,7 @@ namespace Trinity
     DECLSPEC_NORETURN TC_COMMON_API void Error(char const* file, int line, char const* function, char const* message) ATTR_NORETURN;
 
     DECLSPEC_NORETURN TC_COMMON_API void Abort(char const* file, int line, char const* function) ATTR_NORETURN;
+    DECLSPEC_NORETURN TC_COMMON_API void Abort(char const* file, int line, char const* function, char const* message, ...) ATTR_NORETURN;
 
     TC_COMMON_API void Warning(char const* file, int line, char const* function, char const* message);
 
@@ -54,6 +55,7 @@ namespace Trinity
 #define WPError(cond, msg) ASSERT_BEGIN do { if (!(cond)) Trinity::Error(__FILE__, __LINE__, __FUNCTION__, (msg)); } while(0) ASSERT_END
 #define WPWarning(cond, msg) ASSERT_BEGIN do { if (!(cond)) Trinity::Warning(__FILE__, __LINE__, __FUNCTION__, (msg)); } while(0) ASSERT_END
 #define WPAbort() ASSERT_BEGIN do { Trinity::Abort(__FILE__, __LINE__, __FUNCTION__); } while(0) ASSERT_END
+#define WPAbort_MSG(msg, ...) ASSERT_BEGIN do { Trinity::Abort(__FILE__, __LINE__, __FUNCTION__, (msg), ##__VA_ARGS__); } while(0) ASSERT_END
 
 #ifdef PERFORMANCE_PROFILING
 #define ASSERT(cond, ...) ((void)0)
@@ -62,6 +64,7 @@ namespace Trinity
 #endif
 
 #define ABORT WPAbort
+#define ABORT_MSG WPAbort_MSG
 
 template <typename T> inline T* ASSERT_NOTNULL(T* pointer)
 {
diff --git a/src/common/Debugging/WheatyExceptionReport.cpp b/src/common/Debugging/WheatyExceptionReport.cpp
index 32e9051f1a..0384ab4b58 100644
--- a/src/common/Debugging/WheatyExceptionReport.cpp
+++ b/src/common/Debugging/WheatyExceptionReport.cpp
@@ -264,7 +264,7 @@ BOOL WheatyExceptionReport::_GetWindowsVersion(TCHAR* szVersion, DWORD cntMax)
     RTL_OSVERSIONINFOEXW osvi = { };
     osvi.dwOSVersionInfoSize = sizeof(RTL_OSVERSIONINFOEXW);
     NTSTATUS bVersionEx = RtlGetVersion((PRTL_OSVERSIONINFOW)&osvi);
-    if (bVersionEx < 0)
+    if (FAILED(bVersionEx))
     {
         osvi.dwOSVersionInfoSize = sizeof(RTL_OSVERSIONINFOW);
         if (!RtlGetVersion((PRTL_OSVERSIONINFOW)&osvi))
diff --git a/src/common/Utilities/Util.cpp b/src/common/Utilities/Util.cpp
index 68bfe601f5..10e8bf16d5 100644
--- a/src/common/Utilities/Util.cpp
+++ b/src/common/Utilities/Util.cpp
@@ -28,11 +28,27 @@
 #include <cstdarg>
 #include <ctime>
 
-#if TRINITY_COMPILER == TRINITY_COMPILER_GNU
-  #include <sys/socket.h>
-  #include <netinet/in.h>
-  #include <arpa/inet.h>
+void Trinity::VerifyOsVersion()
+{
+#if TRINITY_PLATFORM == TRINITY_PLATFORM_WINDOWS
+    auto isWindowsBuildGreaterOrEqual = [](DWORD build)
+        {
+            OSVERSIONINFOEX osvi = { sizeof(osvi), 0, 0, build, 0, {0}, 0, 0, 0, 0 };
+            ULONGLONG conditionMask = 0;
+            VER_SET_CONDITION(conditionMask, VER_BUILDNUMBER, VER_GREATER_EQUAL);
+
+            return VerifyVersionInfo(&osvi, VER_BUILDNUMBER, conditionMask);
+        };
+
+    if (!isWindowsBuildGreaterOrEqual(TRINITY_REQUIRED_WINDOWS_BUILD))
+    {
+        OSVERSIONINFOEX osvi = { sizeof(osvi), 0, 0, 0, 0, {0}, 0, 0, 0, 0 };
+        GetVersionEx((LPOSVERSIONINFO)&osvi);
+        ABORT_MSG("TrinityCore requires Windows 10 19H1 (1903) or Windows Server 2019 (1903) - require build number 10.0.%d but found %d.%d.%d",
+            TRINITY_REQUIRED_WINDOWS_BUILD, osvi.dwMajorVersion, osvi.dwMinorVersion, osvi.dwBuildNumber);
+    }
 #endif
+}
 
 Tokenizer::Tokenizer(const std::string &src, const char sep, uint32 vectorReserve /*= 0*/, bool keepEmptyStrings /*= true*/)
 {
diff --git a/src/common/Utilities/Util.h b/src/common/Utilities/Util.h
index cc2bfa879d..d75c7c3169 100644
--- a/src/common/Utilities/Util.h
+++ b/src/common/Utilities/Util.h
@@ -25,6 +25,11 @@
 #include <sstream>
 #include <vector>
 
+namespace Trinity
+{
+    TC_COMMON_API void VerifyOsVersion();
+}
+
 class TC_COMMON_API Tokenizer
 {
 public:
diff --git a/src/server/bnetserver/Main.cpp b/src/server/bnetserver/Main.cpp
index 7091808180..839da862f2 100644
--- a/src/server/bnetserver/Main.cpp
+++ b/src/server/bnetserver/Main.cpp
@@ -88,6 +88,8 @@ int main(int argc, char** argv)
 {
     signal(SIGABRT, &Trinity::AbortHandler);
 
+    Trinity::VerifyOsVersion();
+
     auto configFile = fs::absolute(_TRINITY_BNET_CONFIG);
     std::string configService;
     auto vm = GetConsoleArguments(argc, argv, configFile, configService);
diff --git a/src/server/worldserver/Main.cpp b/src/server/worldserver/Main.cpp
index c223dd1824..65f89d73b7 100644
--- a/src/server/worldserver/Main.cpp
+++ b/src/server/worldserver/Main.cpp
@@ -133,6 +133,8 @@ extern int main(int argc, char** argv)
 {
     signal(SIGABRT, &Trinity::AbortHandler);
 
+    Trinity::VerifyOsVersion();
+
     auto configFile = fs::absolute(_TRINITY_CORE_CONFIG);
     std::string configService;
 
diff --git a/src/tools/map_extractor/System.cpp b/src/tools/map_extractor/System.cpp
index d6d5988433..a0a22e2e46 100644
--- a/src/tools/map_extractor/System.cpp
+++ b/src/tools/map_extractor/System.cpp
@@ -16,6 +16,7 @@
  */
 
 #include "StringFormat.h"
+#include "Util.h"
 #include "MapDefines.h"
 #include <boost/filesystem/path.hpp>
 #include <boost/filesystem/operations.hpp>
@@ -1373,6 +1374,8 @@ void LoadCommonMPQFiles(uint32 build)
 
 int main(int argc, char * arg[])
 {
+    Trinity::VerifyOsVersion();
+
     Trinity::Banner::Show("Map & DBC Extractor", [](char const* text) { printf("%s\n", text); }, nullptr);
 
     PrintProgress = isatty(fileno(stdout));
diff --git a/src/tools/mmaps_generator/PathGenerator.cpp b/src/tools/mmaps_generator/PathGenerator.cpp
index 5d30b8dd55..3a216ba461 100644
--- a/src/tools/mmaps_generator/PathGenerator.cpp
+++ b/src/tools/mmaps_generator/PathGenerator.cpp
@@ -344,6 +344,8 @@ std::unordered_map<uint32, std::vector<uint32>> LoadMap(std::string const& local
 
 int main(int argc, char** argv)
 {
+    Trinity::VerifyOsVersion();
+
     Trinity::Banner::Show("MMAP generator", [](char const* text) { printf("%s\n", text); }, nullptr);
 
     unsigned int threads = std::thread::hardware_concurrency();
diff --git a/src/tools/vmap4_assembler/VMapAssembler.cpp b/src/tools/vmap4_assembler/VMapAssembler.cpp
index 2e55f16240..13dd30883c 100644
--- a/src/tools/vmap4_assembler/VMapAssembler.cpp
+++ b/src/tools/vmap4_assembler/VMapAssembler.cpp
@@ -20,9 +20,12 @@
 
 #include "TileAssembler.h"
 #include "Banner.h"
+#include "Util.h"
 
 int main(int argc, char* argv[])
 {
+    Trinity::VerifyOsVersion();
+
     Trinity::Banner::Show("VMAP assembler", [](char const* text) { std::cout << text << std::endl; }, nullptr);
 
     std::string src = "Buildings";
diff --git a/src/tools/vmap4_extractor/vmapexport.cpp b/src/tools/vmap4_extractor/vmapexport.cpp
index 6430846b1a..27e6f8b80d 100644
--- a/src/tools/vmap4_extractor/vmapexport.cpp
+++ b/src/tools/vmap4_extractor/vmapexport.cpp
@@ -21,6 +21,7 @@
 #include "mpqfile.h"
 #include "wmo.h"
 #include "StringFormat.h"
+#include "Util.h"
 #include "vmapexport.h"
 #include "VMapDefinitions.h"
 #include "Banner.h"
@@ -476,6 +477,8 @@ bool processArgv(int argc, char ** argv, const char *versionString)
 
 int main(int argc, char ** argv)
 {
+    Trinity::VerifyOsVersion();
+
     Trinity::Banner::Show("VMAP data extractor", [](char const* text) { printf("%s\n", text); }, nullptr);
 
     input_path = boost::filesystem::current_path();