diff --git a/src/openrct2-ui/UiContext.cpp b/src/openrct2-ui/UiContext.cpp
index 4d02484f1e..b061cbb17b 100644
--- a/src/openrct2-ui/UiContext.cpp
+++ b/src/openrct2-ui/UiContext.cpp
@@ -640,6 +640,30 @@ public:
         _platformUiContext->ShowMessageBox(_window, message);
     }
 
+    int32_t ShowMessageBox(
+        const std::string& title, const std::string& message, const std::vector<std::string>& options) override
+    {
+        auto message_box_button_data = std::make_unique<SDL_MessageBoxButtonData[]>(options.size());
+        for (size_t i = 0; i < options.size(); i++)
+        {
+            message_box_button_data[i].buttonid = static_cast<int>(i);
+            message_box_button_data[i].text = options[i].c_str();
+        }
+
+        SDL_MessageBoxData message_box_data{};
+        message_box_data.window = _window;
+        message_box_data.title = title.c_str();
+        message_box_data.message = message.c_str();
+        message_box_data.numbuttons = static_cast<int>(options.size());
+        message_box_data.buttons = message_box_button_data.get();
+
+        int buttonid{};
+
+        SDL_ShowMessageBox(&message_box_data, &buttonid);
+
+        return buttonid;
+    }
+
     bool HasMenuSupport() override
     {
         return _platformUiContext->HasMenuSupport();
diff --git a/src/openrct2/Context.cpp b/src/openrct2/Context.cpp
index 4bc6e7eef9..e9cb9ae8f3 100644
--- a/src/openrct2/Context.cpp
+++ b/src/openrct2/Context.cpp
@@ -541,6 +541,18 @@ namespace OpenRCT2
             const std::string& path, bool loadTitleScreenOnFail = false, bool asScenario = false) final override
         {
             log_verbose("Context::LoadParkFromFile(%s)", path.c_str());
+
+            // Register the file for crash upload if it asserts while loading.
+            crash_register_additional_file("load_park", path);
+            // Deregister park file in case it was processed without hitting an assert.
+            struct foo
+            {
+                ~foo()
+                {
+                    crash_unregister_additional_file("load_park");
+                }
+            } f;
+
             try
             {
                 if (String::Equals(Path::GetExtension(path), ".sea", true))
diff --git a/src/openrct2/core/FileStream.cpp b/src/openrct2/core/FileStream.cpp
index b95b220fe5..bfe8ee70bc 100644
--- a/src/openrct2/core/FileStream.cpp
+++ b/src/openrct2/core/FileStream.cpp
@@ -184,9 +184,11 @@ namespace OpenRCT2
         {
             return;
         }
-        if (fwrite(buffer, static_cast<size_t>(length), 1, _file) != 1)
+        if (auto count = fwrite(buffer, static_cast<size_t>(length), 1, _file); count != 1)
         {
-            throw IOException("Unable to write to file.");
+            std::string error = "Unable to write " + std::to_string(length) + " bytes to file. Count = " + std::to_string(count)
+                + ", errno = " + std::to_string(errno);
+            throw IOException(error);
         }
 
         uint64_t position = GetPosition();
diff --git a/src/openrct2/park/ParkFile.cpp b/src/openrct2/park/ParkFile.cpp
index 2273bb1145..871c5406af 100644
--- a/src/openrct2/park/ParkFile.cpp
+++ b/src/openrct2/park/ParkFile.cpp
@@ -49,6 +49,7 @@
 #include "../scenario/Scenario.h"
 #include "../scenario/ScenarioRepository.h"
 #include "../scripting/ScriptEngine.h"
+#include "../ui/UiContext.h"
 #include "../world/Climate.h"
 #include "../world/Entrance.h"
 #include "../world/Map.h"
@@ -2312,6 +2313,31 @@ int32_t scenario_save(u8string_view path, int32_t flags)
     catch (const std::exception& e)
     {
         log_error(e.what());
+
+        Formatter ft;
+        ft.Add<const char*>(e.what());
+        context_show_error(STR_FILE_DIALOG_TITLE_SAVE_SCENARIO, STR_STRING, ft);
+        gfx_invalidate_screen();
+
+        auto ctx = OpenRCT2::GetContext();
+        auto uictx = ctx->GetUiContext();
+
+        std::string title = "Error while saving";
+        std::string message
+            = "There was an error while saving scenario.\nhttps://github.com/OpenRCT2/OpenRCT2/issues/17664\nWe would like to "
+              "collect more information about this issue, if this did not happen due to missing permissions, lack of space, "
+              "etc. please consider submitting a bug report. To collect information we would like to trigger an assert.";
+
+        std::string report_bug_button = "Report bug, trigger an assert, potentially terminating the game";
+        std::string skip_button = "Skip reporting, let me continue";
+
+        std::vector<std::string> buttons{ std::move(report_bug_button), std::move(skip_button) };
+        int choice = uictx->ShowMessageBox(title, message, buttons);
+
+        if (choice == 0)
+        {
+            Guard::Assert(false, "Error while saving: %s", e.what());
+        }
     }
 
     gfx_invalidate_screen();
diff --git a/src/openrct2/platform/Crash.cpp b/src/openrct2/platform/Crash.cpp
index 130a6e2349..b88157d805 100644
--- a/src/openrct2/platform/Crash.cpp
+++ b/src/openrct2/platform/Crash.cpp
@@ -47,13 +47,14 @@
 #    define WSZ(x) L"" x
 
 #    ifdef OPENRCT2_COMMIT_SHA1_SHORT
-const wchar_t* _wszCommitSha1Short = WSZ(OPENRCT2_COMMIT_SHA1_SHORT);
+static const wchar_t* _wszCommitSha1Short = WSZ(OPENRCT2_COMMIT_SHA1_SHORT);
 #    else
-const wchar_t* _wszCommitSha1Short = WSZ("");
+static const wchar_t* _wszCommitSha1Short = WSZ("");
 #    endif
 
 // OPENRCT2_ARCHITECTURE is required to be defined in version.h
-const wchar_t* _wszArchitecture = WSZ(OPENRCT2_ARCHITECTURE);
+static const wchar_t* _wszArchitecture = WSZ(OPENRCT2_ARCHITECTURE);
+static std::map<std::wstring, std::wstring> _uploadFiles;
 
 #    define BACKTRACE_TOKEN L"0ca992e20aca116b5e090fd2eaff6e7b5c8225f778fd8f4e77cb077d70329324"
 
@@ -114,8 +115,6 @@ static bool OnCrash(
         return succeeded;
     }
 
-    std::map<std::wstring, std::wstring> uploadFiles;
-
     // Get filenames
     wchar_t dumpFilePath[MAX_PATH];
     wchar_t saveFilePath[MAX_PATH];
@@ -147,7 +146,7 @@ static bool OnCrash(
             // advertise it officially.
 
             /*
-            uploadFiles[L"upload_file_minidump"] = dumpFilePathGZIP;
+            _uploadFiles[L"upload_file_minidump"] = dumpFilePathGZIP;
             */
         }
         fclose(input);
@@ -161,7 +160,7 @@ static bool OnCrash(
     {
         std::wcscpy(dumpFilePath, dumpFilePathNew);
     }
-    uploadFiles[L"upload_file_minidump"] = dumpFilePath;
+    _uploadFiles[L"upload_file_minidump"] = dumpFilePath;
 
     // Compress to gzip-compatible stream
 
@@ -195,13 +194,13 @@ static bool OnCrash(
     // Compress the save
     if (savedGameDumped)
     {
-        uploadFiles[L"attachment_park.park"] = saveFilePath;
+        _uploadFiles[L"attachment_park.park"] = saveFilePath;
     }
 
     auto configFilePathUTF8 = String::ToUtf8(configFilePath);
     if (config_save(configFilePathUTF8))
     {
-        uploadFiles[L"attachment_config.ini"] = configFilePath;
+        _uploadFiles[L"attachment_config.ini"] = configFilePath;
     }
 
     // janisozaur: https://github.com/OpenRCT2/OpenRCT2/pull/17634
@@ -219,7 +218,7 @@ static bool OnCrash(
         if (!screenshotPath.empty())
         {
             auto screenshotPathW = String::ToWideChar(screenshotPath.c_str());
-            uploadFiles[L"attachment_screenshot.png"] = screenshotPathW;
+            _uploadFiles[L"attachment_screenshot.png"] = screenshotPathW;
         }
     }
 
@@ -229,7 +228,7 @@ static bool OnCrash(
         bool record_copied = CopyFileW(parkReplayPathW.c_str(), recordFilePathNew, true);
         if (record_copied)
         {
-            uploadFiles[L"attachment_replay.parkrep"] = recordFilePathNew;
+            _uploadFiles[L"attachment_replay.parkrep"] = recordFilePathNew;
         }
         else
         {
@@ -242,7 +241,7 @@ static bool OnCrash(
         printf("Uploading minidump in silent mode...\n");
         int error;
         std::wstring response;
-        UploadMinidump(uploadFiles, error, response);
+        UploadMinidump(_uploadFiles, error, response);
         return succeeded;
     }
 
@@ -260,7 +259,7 @@ static bool OnCrash(
     {
         int error;
         std::wstring response;
-        bool ok = UploadMinidump(uploadFiles, error, response);
+        bool ok = UploadMinidump(_uploadFiles, error, response);
         if (!ok)
         {
             const wchar_t* MessageFormat2 = L"There was a problem while uploading the dump. Please upload it manually to "
@@ -340,3 +339,21 @@ CExceptionHandler crash_init()
     return nullptr;
 #endif // USE_BREAKPAD
 }
+
+void crash_register_additional_file(const std::string& key, const std::string& path)
+{
+#ifdef USE_BREAKPAD
+    _uploadFiles[String::ToWideChar(key.c_str())] = String::ToWideChar(path.c_str());
+#endif // USE_BREAKPAD
+}
+
+void crash_unregister_additional_file(const std::string& key)
+{
+#ifdef USE_BREAKPAD
+    auto it = _uploadFiles.find(String::ToWideChar(key.c_str()));
+    if (it != _uploadFiles.end())
+    {
+        _uploadFiles.erase(it);
+    }
+#endif // USE_BREAKPAD
+}
diff --git a/src/openrct2/platform/Crash.h b/src/openrct2/platform/Crash.h
index 46c4a1c966..51caa4237f 100644
--- a/src/openrct2/platform/Crash.h
+++ b/src/openrct2/platform/Crash.h
@@ -9,7 +9,11 @@
 
 #pragma once
 
+#include <string>
+
 using CExceptionHandler = void*;
 
 extern bool gOpenRCT2SilentBreakpad;
 CExceptionHandler crash_init();
+void crash_register_additional_file(const std::string& key, const std::string& path);
+void crash_unregister_additional_file(const std::string& key);
diff --git a/src/openrct2/ui/DummyUiContext.cpp b/src/openrct2/ui/DummyUiContext.cpp
index aa573ae300..d4040832e6 100644
--- a/src/openrct2/ui/DummyUiContext.cpp
+++ b/src/openrct2/ui/DummyUiContext.cpp
@@ -90,6 +90,10 @@ namespace OpenRCT2::Ui
         void ShowMessageBox(const std::string& /*message*/) override
         {
         }
+        int32_t ShowMessageBox(const std::string&, const std::string&, const std::vector<std::string>&) override
+        {
+            return -1;
+        }
         bool HasMenuSupport() override
         {
             return false;
diff --git a/src/openrct2/ui/UiContext.h b/src/openrct2/ui/UiContext.h
index 3660fc42f4..142b79d874 100644
--- a/src/openrct2/ui/UiContext.h
+++ b/src/openrct2/ui/UiContext.h
@@ -120,6 +120,8 @@ namespace OpenRCT2
             virtual void TriggerResize() abstract;
 
             virtual void ShowMessageBox(const std::string& message) abstract;
+            virtual int32_t ShowMessageBox(
+                const std::string& title, const std::string& message, const std::vector<std::string>& options) abstract;
 
             virtual bool HasMenuSupport() abstract;
             // Creates a menu with a series of options, returns the index of the selected option