diff --git a/include/Compat.h b/include/Compat.h
index e1e906d..1a3cc63 100644
--- a/include/Compat.h
+++ b/include/Compat.h
@@ -6,10 +6,10 @@
 
 #ifdef BEAMMP_LINUX
 #include <arpa/inet.h>
+#include <errno.h>
 #include <sys/socket.h>
 #include <termios.h>
 #include <unistd.h>
-#include <errno.h>
 using SOCKET = int;
 using DWORD = unsigned long;
 using PDWORD = unsigned long*;
@@ -25,10 +25,10 @@ inline void CloseSocketProper(int TheSocket) {
 
 #ifdef BEAMMP_APPLE
 #include <arpa/inet.h>
+#include <errno.h>
 #include <sys/socket.h>
 #include <termios.h>
 #include <unistd.h>
-#include <errno.h>
 using SOCKET = int;
 using DWORD = unsigned long;
 using PDWORD = unsigned long*;
@@ -48,6 +48,11 @@ inline void CloseSocketProper(int TheSocket) {
 inline void CloseSocketProper(SOCKET TheSocket) {
     shutdown(TheSocket, 2); // 2 == SD_BOTH
     closesocket(TheSocket);
-
 }
 #endif // WIN32
+
+#ifdef INVALID_SOCKET
+static inline constexpr int BEAMMP_INVALID_SOCKET = INVALID_SOCKET;
+#else
+static inline constexpr int BEAMMP_INVALID_SOCKET = -1;
+#endif
diff --git a/src/Common.cpp b/src/Common.cpp
index 43c1253..efdf240 100644
--- a/src/Common.cpp
+++ b/src/Common.cpp
@@ -43,6 +43,7 @@ void Application::GracefullyShutdown() {
         beammp_info("Subsystem " + std::to_string(i + 1) + "/" + std::to_string(mShutdownHandlers.size()) + " shutting down");
         mShutdownHandlers[i]();
     }
+    // std::exit(-1);
 }
 
 std::string Application::ServerVersionString() {
@@ -105,7 +106,7 @@ void Application::CheckForUpdates() {
         if (Matches) {
             auto MyVersion = ServerVersion();
             auto RemoteVersion = Version(VersionStrToInts(Response));
-            if (!IsOutdated(MyVersion, RemoteVersion)) {
+            if (IsOutdated(MyVersion, RemoteVersion)) {
                 std::string RealVersionString = RemoteVersion.AsString();
                 beammp_warn(std::string(ANSI_YELLOW_BOLD) + "NEW VERSION OUT! There's a new version (v" + RealVersionString + ") of the BeamMP-Server available! For more info visit https://wiki.beammp.com/en/home/server-maintenance#updating-the-server." + std::string(ANSI_RESET));
             } else {
diff --git a/src/TNetwork.cpp b/src/TNetwork.cpp
index 1e0e5be..6a86788 100644
--- a/src/TNetwork.cpp
+++ b/src/TNetwork.cpp
@@ -108,40 +108,48 @@ void TNetwork::TCPServerMain() {
 #if defined(BEAMMP_WINDOWS)
     WSADATA wsaData;
     if (WSAStartup(514, &wsaData)) {
-        beammp_error("Can't start Winsock!");
-        return;
+        beammp_error("Can't start Winsock! Shutting down");
+        Application::GracefullyShutdown();
     }
 #endif // WINDOWS
     TConnection client {};
     SOCKET Listener = socket(AF_INET, SOCK_STREAM, IPPROTO_TCP);
-    int optval = 1;
+    if (Listener == BEAMMP_INVALID_SOCKET) {
+        beammp_error("Failed to create socket: " + GetPlatformAgnosticErrorString()
+        + ". This is a fatal error, as a socket is needed for the server to operate. Shutting down.");
+        Application::GracefullyShutdown();
+    }
 #if defined(BEAMMP_WINDOWS)
-    const char* optval_ptr = reinterpret_cast<const char*>(&optval);
+    const char optval = 0;
+    int ret = ::setsockopt(Listener, SOL_SOCKET, SO_DONTLINGER, &optval, sizeof(optval));
 #elif defined(BEAMMP_LINUX) || defined(BEAMMP_APPLE)
-    void* optval_ptr = reinterpret_cast<void*>(&optval);
+    int optval = true;
+    int ret = ::setsockopt(Listener, SOL_SOCKET, SO_REUSEADDR, reinterpret_cast<void*>(&optval), sizeof(optval));
 #endif
-    setsockopt(Listener, SOL_SOCKET, SO_REUSEADDR, optval_ptr, sizeof(optval));
-    // TODO: check optval or return value idk
+    // not a fatal error
+    if (ret < 0) {
+        beammp_error("Failed to set up listening socket to not linger / reuse address. "
+                     "This may cause the socket to refuse to bind(). Error: "
+            + GetPlatformAgnosticErrorString());
+    }
     sockaddr_in addr {};
     addr.sin_addr.s_addr = INADDR_ANY;
     addr.sin_family = AF_INET;
     addr.sin_port = htons(uint16_t(Application::Settings.Port));
-    if (bind(Listener, (sockaddr*)&addr, sizeof(addr)) != 0) {
-        beammp_error("bind() failed: " + GetPlatformAgnosticErrorString());
-        std::this_thread::sleep_for(std::chrono::seconds(5));
-        exit(-1); // TODO: Wtf.
+    if (bind(Listener, (sockaddr*)&addr, sizeof(addr)) < 0) {
+        beammp_error("bind() failed, the server cannot operate and will shut down now. "
+                     "Error: "
+            + GetPlatformAgnosticErrorString());
+        Application::GracefullyShutdown();
     }
-    if (Listener == -1) {
-        beammp_error("Invalid listening socket");
-        return;
-    }
-    if (listen(Listener, SOMAXCONN)) {
-        beammp_error("listen() failed: " + GetPlatformAgnosticErrorString());
-        // FIXME leak Listener
-        return;
+    if (listen(Listener, SOMAXCONN) < 0) {
+        beammp_error("listen() failed, which is needed for the server to operate. "
+                     "Shutting down. Error: "
+            + GetPlatformAgnosticErrorString());
+        Application::GracefullyShutdown();
     }
     Application::SetSubsystemStatus("TCPNetwork", Application::Status::Good);
-    beammp_info(("Vehicle event network online"));
+    beammp_info("Vehicle event network online");
     do {
         try {
             if (mShutdown) {
@@ -157,9 +165,9 @@ void TNetwork::TCPServerMain() {
             std::thread ID(&TNetwork::Identify, this, client);
             ID.detach(); // TODO: Add to a queue and attempt to join periodically
         } catch (const std::exception& e) {
-            beammp_error(("fatal: ") + std::string(e.what()));
+            beammp_error("fatal: " + std::string(e.what()));
         }
-    } while (client.Socket);
+    } while (client.Socket != BEAMMP_INVALID_SOCKET);
 
     beammp_debug("all ok, arrived at " + std::string(__func__) + ":" + std::to_string(__LINE__));