diff --git a/src/crashlog.cpp b/src/crashlog.cpp
index 37b01449c1..bda0d4d9ef 100644
--- a/src/crashlog.cpp
+++ b/src/crashlog.cpp
@@ -86,6 +86,7 @@
 /* static */ const char *CrashLog::message = nullptr;
 /* static */ char *CrashLog::gamelog_buffer = nullptr;
 /* static */ const char *CrashLog::gamelog_last = nullptr;
+/* static */ bool CrashLog::have_crashed = false;
 
 char *CrashLog::LogCompiler(char *buffer, const char *last) const
 {
@@ -921,9 +922,8 @@ static bool CopyAutosave(const std::string &old_name, const std::string &new_nam
 bool CrashLog::MakeCrashLog(char *buffer, const char *last)
 {
 	/* Don't keep looping logging crashes. */
-	static bool crashlogged = false;
-	if (crashlogged) return false;
-	crashlogged = true;
+	if (CrashLog::HaveAlreadyCrashed()) return false;
+	CrashLog::RegisterCrashed();
 
 	char *name_buffer_date = this->name_buffer + seprintf(this->name_buffer, lastof(this->name_buffer), "crash-");
 	UTCTime::Format(name_buffer_date, lastof(this->name_buffer), "%Y%m%dT%H%M%SZ");
diff --git a/src/crashlog.h b/src/crashlog.h
index 3d59860941..7af22007ba 100644
--- a/src/crashlog.h
+++ b/src/crashlog.h
@@ -55,6 +55,9 @@ private:
 	/** Temporary 'local' location of the end of the buffer. */
 	static const char *gamelog_last;
 
+	/** Whether a crash has already occured */
+	static bool have_crashed;
+
 	static void GamelogFillCrashLog(const char *s);
 protected:
 	/**
@@ -208,6 +211,8 @@ public:
 	static void InconsistencyLog(const InconsistencyExtraInfo &info);
 	static void VersionInfoLog();
 
+	static void RegisterCrashed() { CrashLog::have_crashed = true; }
+	static bool HaveAlreadyCrashed() { return CrashLog::have_crashed; }
 	static void SetErrorMessage(const char *message);
 	static void AfterCrashLogCleanup();
 
diff --git a/src/openttd.cpp b/src/openttd.cpp
index b69874d752..cdfa4af13d 100644
--- a/src/openttd.cpp
+++ b/src/openttd.cpp
@@ -168,6 +168,8 @@ void CDECL usererror(const char *s, ...)
  */
 void CDECL error(const char *s, ...)
 {
+	if (CrashLog::HaveAlreadyCrashed()) DoOSAbort();
+
 	va_list va;
 	char buf[2048];
 
@@ -186,6 +188,8 @@ void CDECL error(const char *s, ...)
 
 void CDECL assert_msg_error(int line, const char *file, const char *expr, const char *extra, const char *str, ...)
 {
+	if (CrashLog::HaveAlreadyCrashed()) DoOSAbort();
+
 	va_list va;
 	char buf[2048];
 
@@ -200,7 +204,9 @@ void CDECL assert_msg_error(int line, const char *file, const char *expr, const
 	vseprintf(b, lastof(buf), str, va);
 	va_end(va);
 
-	ShowOSErrorBox(buf, true);
+	if (VideoDriver::GetInstance() == nullptr || VideoDriver::GetInstance()->HasGUI()) {
+		ShowOSErrorBox(buf, true);
+	}
 
 	/* Set the error message for the crash log and then invoke it. */
 	CrashLog::SetErrorMessage(buf);
diff --git a/src/os/macosx/crashlog_osx.cpp b/src/os/macosx/crashlog_osx.cpp
index 1dc1321674..64ba172d9b 100644
--- a/src/os/macosx/crashlog_osx.cpp
+++ b/src/os/macosx/crashlog_osx.cpp
@@ -486,6 +486,8 @@ static const int _signals_to_handle[] = { SIGSEGV, SIGABRT, SIGFPE, SIGBUS, SIGI
  */
 void CDECL HandleCrash(int signum, siginfo_t *si, void *context)
 {
+	CrashLog::RegisterCrashed();
+
 	/* Disable all handling of signals by us, so we don't go into infinite loops. */
 	for (const int *i = _signals_to_handle; i != endof(_signals_to_handle); i++) {
 		signal(*i, SIG_DFL);
diff --git a/src/os/windows/crashlog_win.cpp b/src/os/windows/crashlog_win.cpp
index 648edc2bcd..e7efdd64bd 100644
--- a/src/os/windows/crashlog_win.cpp
+++ b/src/os/windows/crashlog_win.cpp
@@ -762,6 +762,8 @@ thread_local void *_safe_esp = nullptr;
 
 static LONG WINAPI ExceptionHandler(EXCEPTION_POINTERS *ep)
 {
+	CrashLog::RegisterCrashed();
+
 	/* Restore system timer resolution. */
 	timeEndPeriod(1);