diff --git a/openloco.common.props b/openloco.common.props
index c8013b39..55f048fb 100644
--- a/openloco.common.props
+++ b/openloco.common.props
@@ -50,7 +50,7 @@
              C4549: 'operator': operator before comma has no effect; did you intend 'operator'?
              C4555: expression has no effect; expected expression with side-effect
       -->
-      <PreprocessorDefinitions>_CRT_SECURE_NO_WARNINGS;_CRT_NONSTDC_NO_DEPRECATE;_USE_MATH_DEFINES;SDL_MAIN_HANDLED;_WINSOCK_DEPRECATED_NO_WARNINGS;%(PreprocessorDefinitions)</PreprocessorDefinitions>
+      <PreprocessorDefinitions>_CRT_SECURE_NO_WARNINGS;_CRT_NONSTDC_NO_DEPRECATE;_USE_MATH_DEFINES;SDL_MAIN_HANDLED;_WINSOCK_DEPRECATED_NO_WARNINGS;USE_BREAKPAD;%(PreprocessorDefinitions)</PreprocessorDefinitions>
       <MultiProcessorCompilation>true</MultiProcessorCompilation>
       <TreatWarningAsError>true</TreatWarningAsError>
       <AdditionalOptions>/utf-8 /std:c++17 /permissive-</AdditionalOptions>
diff --git a/src/OpenLoco/OpenLoco.cpp b/src/OpenLoco/OpenLoco.cpp
index 4fb4df72..e1c5e34f 100644
--- a/src/OpenLoco/OpenLoco.cpp
+++ b/src/OpenLoco/OpenLoco.cpp
@@ -46,6 +46,7 @@
 #include "MultiPlayer.h"
 #include "Objects/ObjectManager.h"
 #include "OpenLoco.h"
+#include "Platform/Crash.h"
 #include "Platform/Platform.h"
 #include "S5/S5.h"
 #include "Scenario.h"
@@ -1158,6 +1159,7 @@ namespace OpenLoco
     // 0x00406D13
     void main()
     {
+        crash_init();
         auto versionInfo = OpenLoco::getVersionInfo();
         std::cout << versionInfo << std::endl;
         try
diff --git a/src/OpenLoco/Platform/Crash.cpp b/src/OpenLoco/Platform/Crash.cpp
new file mode 100644
index 00000000..9571b7e1
--- /dev/null
+++ b/src/OpenLoco/Platform/Crash.cpp
@@ -0,0 +1,79 @@
+#include "Crash.h"
+#if defined(USE_BREAKPAD)
+#include "../Utility/String.hpp"
+#include "Platform.h"
+#include <ShlObj.h>
+#include <client/windows/handler/exception_handler.h>
+
+#if defined(OPENLOCO_COMMIT_SHA1_SHORT)
+const wchar_t* _wszCommitSha1Short = L"" OPENLOCO_COMMIT_SHA1_SHORT;
+#else
+const wchar_t* _wszCommitSha1Short = L"Unknown";
+#endif
+
+static bool OnCrash(
+    const wchar_t* dumpPath, const wchar_t* miniDumpId, void* context, EXCEPTION_POINTERS* exinfo,
+    MDRawAssertionInfo* assertion, bool succeeded)
+{
+    if (!succeeded)
+    {
+        constexpr const char* DumpFailedMessage = "Failed to create the dump. Please file an issue with OpenLoco on GitHub and "
+                                                  "provide latest save, and provide "
+                                                  "information about what you did before the crash occurred.";
+        printf("%s\n", DumpFailedMessage);
+        MessageBoxA(nullptr, DumpFailedMessage, "OpenLoco", MB_OK | MB_ICONERROR);
+        return succeeded;
+    }
+    wchar_t dumpFilePath[MAX_PATH];
+    swprintf_s(dumpFilePath, std::size(dumpFilePath), L"%s\\%s.dmp", dumpPath, miniDumpId);
+    constexpr const wchar_t* MessageFormat = L"A crash has occurred and a dump was created at\n%s.\n\nPlease file an issue "
+                                             L"with OpenLoco on GitHub and provide "
+                                             L"the dump and saved game there.\n\n\nCommit: %s\n\n";
+    wchar_t message[MAX_PATH * 2];
+    swprintf_s(message, MessageFormat, dumpFilePath, _wszCommitSha1Short);
+    MessageBoxW(nullptr, message, L"OpenLoco", MB_OK | MB_ICONERROR);
+
+    HRESULT coInitializeResult = CoInitialize(nullptr);
+    if (SUCCEEDED(coInitializeResult))
+    {
+        LPITEMIDLIST pidl = ILCreateFromPathW(dumpPath);
+        LPITEMIDLIST files[6];
+        uint32_t numFiles = 0;
+
+        files[numFiles++] = ILCreateFromPathW(dumpFilePath);
+        if (pidl != nullptr)
+        {
+            SHOpenFolderAndSelectItems(pidl, numFiles, (LPCITEMIDLIST*)files, 0);
+            ILFree(pidl);
+            for (uint32_t i = 0; i < numFiles; i++)
+            {
+                ILFree(files[i]);
+            }
+        }
+        CoUninitialize();
+    }
+    return succeeded;
+}
+
+static std::wstring GetDumpDirectory()
+{
+    auto user_dir = OpenLoco::platform::getUserDirectory();
+    auto result = OpenLoco::Utility::toUtf16(user_dir.string());
+    return result;
+}
+#endif // USE_BREAKPAD
+
+// Using non-null pipe name here lets breakpad try setting OOP crash handling
+constexpr const wchar_t* PipeName = L"openloco-bpad";
+
+CExceptionHandler crash_init()
+{
+#if defined(USE_BREAKPAD)
+    // Path must exist and be RW!
+    auto exHandler = new google_breakpad::ExceptionHandler(
+        GetDumpDirectory(), 0, OnCrash, 0, google_breakpad::ExceptionHandler::HANDLER_ALL, MiniDumpWithDataSegs, PipeName, 0);
+    return reinterpret_cast<CExceptionHandler>(exHandler);
+#else  // USE_BREAKPAD
+    return nullptr;
+#endif // USE_BREAKPAD
+}
diff --git a/src/OpenLoco/Platform/Crash.h b/src/OpenLoco/Platform/Crash.h
new file mode 100644
index 00000000..496d5a49
--- /dev/null
+++ b/src/OpenLoco/Platform/Crash.h
@@ -0,0 +1,3 @@
+#pragma once
+using CExceptionHandler = void*;
+CExceptionHandler crash_init();
diff --git a/src/OpenLoco/openloco.vcxproj b/src/OpenLoco/openloco.vcxproj
index cd5c5ff4..6005840c 100644
--- a/src/OpenLoco/openloco.vcxproj
+++ b/src/OpenLoco/openloco.vcxproj
@@ -100,6 +100,7 @@
     <ClCompile Include="Paint\PaintEntity.cpp" />
     <ClCompile Include="Paint\PaintMiscEntity.cpp" />
     <ClCompile Include="Paint\PaintVehicle.cpp" />
+    <ClCompile Include="Platform\Crash.cpp" />
     <ClCompile Include="Platform\Platform.Posix.cpp" />
     <ClCompile Include="Platform\Platform.Windows.cpp" />
     <ClCompile Include="S5\S5.cpp" />