diff --git a/engine/system/sys_main.h b/engine/system/sys_main.h
index 5d83fc78..e2ffb447 100644
--- a/engine/system/sys_main.h
+++ b/engine/system/sys_main.h
@@ -50,7 +50,7 @@ class find_c {
 	std::filesystem::directory_iterator iter;
 };
 
-std::string GetWineHostVersion();
+std::tuple<std::string, std::string> GetWineHostVersion();
 
 // ==========
 // Interfaces
diff --git a/engine/system/win/sys_main.cpp b/engine/system/win/sys_main.cpp
index 3078e0d8..67600e1d 100644
--- a/engine/system/win/sys_main.cpp
+++ b/engine/system/win/sys_main.cpp
@@ -434,23 +434,39 @@ void sys_main_c::SpawnProcess(std::filesystem::path cmdName, const char* argList
 #endif
 }
 
-std::string GetWineHostVersion()
+// get wine host OS type and x.y.z format version of wine
+std::tuple<std::string, std::string> GetWineHostVersion()
 {
 #ifdef _WIN32
 	using WineHostVersionFun = void(const char** /*sysname*/, const char** /*release*/);
+	using WineVersionFun = char *();
 	HMODULE mod = GetModuleHandleA("ntdll.dll");
 	if (!mod)
-		return "";
+		return {"", ""};
 	auto ptr = GetProcAddress(mod, "wine_get_host_version");
 	if (!ptr)
-		return "";
+		return {"", ""};
+	auto verPtr = GetProcAddress(mod, "wine_get_version");
+	if (!verPtr)
+		return {"", ""};
 	auto fun = (WineHostVersionFun*)ptr;
 	const char* sysname{};
 	const char* release{};
 	fun(&sysname, &release);
-	return sysname ? sysname : "";
+
+	auto verFun = (WineVersionFun *)verPtr;
+	// version in x.y.z format
+	const char *version = verFun();
+	if (sysname && version)
+	{
+		return {sysname, version};
+	}
+	else
+	{
+		return {"", ""};
+	}
 #else
-	return "";
+	return {"", ""};
 #endif
 }
 
@@ -458,14 +474,22 @@ std::string GetWineHostVersion()
 const char* PlatformOpenURL(const char* url)
 {
 #ifdef _WIN32
-	const std::string wineHost = GetWineHostVersion();
-	/*
-	Wine has some loosely determined maximum length on how long of an URL
-	can be, so we pick a "safe" maximum and refuse to open anything longer.
-	*/
-	if ((wineHost == "Linux" || wineHost == "Darwin") && strlen(url) > 1500)
-		return AllocString("Did not open URL, length likely too long for the OS.");
-	ShellExecuteA(NULL, "open", url, NULL, NULL, SW_SHOWDEFAULT);
+	auto [wineHost, wineVersion] = GetWineHostVersion();
+	int major = INT_MAX;
+	int minor = INT_MAX;
+	auto match = RE2::PartialMatch(wineVersion, "^(\\d+)\\.(\\d+)", &major, &minor);
+	// work around a pre-8.17 wine bug where long urls may cause a stack corruption and overflow
+	bool invalidVersion = (major < 8) || (major == 8 && minor < 17);
+	if ((wineHost == "Linux" || wineHost == "Darwin") && strlen(url) > 1500 && invalidVersion)
+	{
+		return AllocString("Did not open URL, length likely too long for pre-8.17 Wine versions.");
+	}
+	auto retVal = (INT_PTR)ShellExecuteA(NULL, "open", url, NULL, NULL, SW_SHOWDEFAULT);
+	// "If the function succeeds, it returns a value greater than 32"
+	if (retVal <= 32)
+	{
+		return AllocString("Opening URL failed.");
+	}
 	return nullptr;
 #else
 #warning LV: URL opening not implemented on this OS.
diff --git a/engine/system/win/sys_video.cpp b/engine/system/win/sys_video.cpp
index 6f61bffb..f8963d11 100644
--- a/engine/system/win/sys_video.cpp
+++ b/engine/system/win/sys_video.cpp
@@ -108,7 +108,7 @@ sys_video_c::sys_video_c(sys_IMain* sysHnd)
 
 	int platformType = GLFW_ANGLE_PLATFORM_TYPE_NONE;
 #ifdef _WIN32
-	const std::string wineHost = GetWineHostVersion();
+	auto [wineHost, _] = GetWineHostVersion();
 	if (wineHost == "Linux")
 		platformType = GLFW_ANGLE_PLATFORM_TYPE_OPENGL;
 	else if (wineHost == "Darwin")