diff --git a/src/openrct2/core/Guard.cpp b/src/openrct2/core/Guard.cpp
index 8419e782f0..94babbc74d 100644
--- a/src/openrct2/core/Guard.cpp
+++ b/src/openrct2/core/Guard.cpp
@@ -45,6 +45,8 @@ namespace Guard
 #endif
         ;
 
+    static std::optional<std::string> _lastAssertMessage = std::nullopt;
+
 #ifdef _WIN32
     static void GetAssertMessage(char* buffer, size_t bufferSize, const char* formattedMessage);
     static void ForceCrash();
@@ -84,6 +86,11 @@ namespace Guard
             Console::Error::WriteLine(formattedMessage);
         }
 
+        if (formattedMessage != nullptr)
+        {
+            _lastAssertMessage = std::make_optional(formattedMessage);
+        }
+
 #ifdef DEBUG
         Debug::Break();
 #endif
@@ -126,6 +133,11 @@ namespace Guard
         Assert_VA(false, message, args);
     }
 
+    std::optional<std::string> GetLastAssertMessage()
+    {
+        return _lastAssertMessage;
+    }
+
 #ifdef _WIN32
     static void GetAssertMessage(char* buffer, size_t bufferSize, const char* formattedMessage)
     {
diff --git a/src/openrct2/core/Guard.hpp b/src/openrct2/core/Guard.hpp
index 5556232fd5..f8b696f30e 100644
--- a/src/openrct2/core/Guard.hpp
+++ b/src/openrct2/core/Guard.hpp
@@ -10,8 +10,10 @@
 #pragma once
 
 #include <memory>
+#include <optional>
 #include <stdarg.h>
 #include <stdbool.h>
+#include <string>
 
 void openrct2_assert_fwd(bool expression, const char* message, ...);
 
@@ -41,6 +43,8 @@ namespace Guard
     void Fail(const char* message = nullptr, ...);
     void Fail_VA(const char* message, va_list args);
 
+    std::optional<std::string> GetLastAssertMessage();
+
     template<typename T> static void ArgumentNotNull(T* argument, const char* message = nullptr, ...)
     {
         va_list args;
diff --git a/src/openrct2/interface/InteractiveConsole.cpp b/src/openrct2/interface/InteractiveConsole.cpp
index e1367cc327..2e4f9ef343 100644
--- a/src/openrct2/interface/InteractiveConsole.cpp
+++ b/src/openrct2/interface/InteractiveConsole.cpp
@@ -1596,6 +1596,15 @@ static int32_t cc_terminate([[maybe_unused]] InteractiveConsole& console, [[mayb
 }
 #pragma warning(pop)
 
+static int32_t cc_assert([[maybe_unused]] InteractiveConsole& console, [[maybe_unused]] const arguments_t& argv)
+{
+    if (!argv.empty())
+        Guard::Assert(false, "%s", argv[0].c_str());
+    else
+        Guard::Assert(false);
+    return 0;
+}
+
 using console_command_func = int32_t (*)(InteractiveConsole& console, const arguments_t& argv);
 struct console_command
 {
@@ -1655,6 +1664,7 @@ static constexpr const utf8* console_window_table[] = {
 
 static constexpr const console_command console_command_table[] = {
     { "abort", cc_abort, "Calls std::abort(), for testing purposes only.", "abort" },
+    { "assert", cc_assert, "Triggers assertion failure, for testing purposes only", "assert" },
     { "clear", cc_clear, "Clears the console.", "clear" },
     { "close", cc_close, "Closes the console.", "close" },
     { "date", cc_for_date, "Sets the date to a given date.", "Format <year>[ <month>[ <day>]]." },
diff --git a/src/openrct2/platform/Crash.cpp b/src/openrct2/platform/Crash.cpp
index b6a5db9fac..40d11e9ebe 100644
--- a/src/openrct2/platform/Crash.cpp
+++ b/src/openrct2/platform/Crash.cpp
@@ -27,6 +27,7 @@
 #    include "../Version.h"
 #    include "../config/Config.h"
 #    include "../core/Console.hpp"
+#    include "../core/Guard.hpp"
 #    include "../core/String.hpp"
 #    include "../interface/Screenshot.h"
 #    include "../localisation/Language.h"
@@ -70,6 +71,13 @@ static bool UploadMinidump(const std::map<std::wstring, std::wstring>& files, in
     {
         parameters[L"commit"] = String::ToWideChar(gVersionInfoFull);
     }
+
+    auto assertMsg = Guard::GetLastAssertMessage();
+    if (assertMsg)
+    {
+        parameters[L"assert_failure"] = String::ToWideChar(*assertMsg);
+    }
+
     int timeout = 10000;
     bool success = google_breakpad::HTTPUpload::SendRequest(url, parameters, files, &timeout, &response, &error);
     wprintf(L"Success = %d, error = %d, response = %s\n", success, error, response.c_str());