diff --git a/CHANGELOG.md b/CHANGELOG.md
index b321a8a..1581864 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -31,6 +31,24 @@ pulls notes from — it's the minimum, the GitHub release page is the maximum.
   events don't loop back into the logger), and the failure path on
   that path writes to `Console.Error` instead of `Log.Warning` so the
   recursion can't restart.
+- **Restart Server no longer probes `systemctl` on Windows.** The
+  `POST /api/server/restart` endpoint always tried
+  `sudo -n systemctl restart 7daystodie.service` first and waited up to
+  5 seconds before falling back to in-game shutdown. On Windows there
+  is no `systemctl`, so every restart click wasted ~5s and logged a
+  misleading `systemctl restart failed or not available...` warning.
+  On a live Windows prod box this code path was the trigger for a
+  cascading crash — the fallback in-game shutdown ran concurrent with
+  a stuck main-thread operation and snowballed into a stack overflow.
+  Fix: new `Core/OsRestartStrategy.cs` picks the path per OS. Windows
+  goes straight to in-game shutdown and relies on the service
+  supervisor (NSSM `AppExit Restart`, which is its default) to bounce
+  7DTD on game exit; an INFO-level log line announces the chosen path
+  instead of the warning. Linux behavior is unchanged — systemctl
+  first, fall back to in-game shutdown for `Restart=always`. Console
+  command `krestart` already uses the OS-agnostic
+  `GracefulRestartFeature.TriggerNow` (no shell-out) so it didn't need
+  to change.
 
 ## [2.8.1] - 2026-05-29
 
diff --git a/src/KitsuneCommand.Tests/Core/OsRestartStrategyTests.cs b/src/KitsuneCommand.Tests/Core/OsRestartStrategyTests.cs
new file mode 100644
index 0000000..20c8aeb
--- /dev/null
+++ b/src/KitsuneCommand.Tests/Core/OsRestartStrategyTests.cs
@@ -0,0 +1,33 @@
+using NUnit.Framework;
+using KitsuneCommand.Core;
+
+namespace KitsuneCommand.Tests.Core
+{
+    /// <summary>
+    /// Covers the pure decision function. The platform-detection probe itself
+    /// (PlatformHelper.IsWindows / DecideForCurrentHost) isn't unit-tested
+    /// here because it just reads Environment.OSVersion.Platform — the
+    /// useful test surface is the strategy mapping, which is pure.
+    /// </summary>
+    [TestFixture]
+    public class OsRestartStrategyTests
+    {
+        [Test]
+        public void Decide_OnWindows_SkipsSystemctlProbe()
+        {
+            var strategy = OsRestartStrategy.Decide(isWindows: true);
+
+            Assert.That(strategy, Is.EqualTo(OsRestartStrategy.Kind.InGameShutdownOnly),
+                "Windows must skip systemctl — NSSM handles the bounce on game exit.");
+        }
+
+        [Test]
+        public void Decide_OnLinux_TriesSystemctlFirst()
+        {
+            var strategy = OsRestartStrategy.Decide(isWindows: false);
+
+            Assert.That(strategy, Is.EqualTo(OsRestartStrategy.Kind.SystemctlThenInGameShutdown),
+                "Linux must keep trying systemctl first; in-game shutdown is the fallback.");
+        }
+    }
+}
diff --git a/src/KitsuneCommand/Core/OsRestartStrategy.cs b/src/KitsuneCommand/Core/OsRestartStrategy.cs
new file mode 100644
index 0000000..091a2cf
--- /dev/null
+++ b/src/KitsuneCommand/Core/OsRestartStrategy.cs
@@ -0,0 +1,52 @@
+namespace KitsuneCommand.Core
+{
+    /// <summary>
+    /// Picks how the Restart Server endpoint should bounce the 7DTD service for
+    /// the current host OS. Two paths exist:
+    ///
+    ///   - Linux: try <c>sudo -n systemctl restart 7daystodie.service</c> first
+    ///     (works if <c>scripts/linux-updater/install-linux-updater.sh</c> has
+    ///     been run to add the sudoers entry), then fall back to in-game
+    ///     shutdown and rely on systemd <c>Restart=always</c>.
+    ///   - Windows: there is no <c>systemctl</c>. NSSM (the standard service
+    ///     supervisor for 7DTD on Windows) ships with <c>AppExit Restart</c>
+    ///     as its default, so an in-game shutdown is sufficient — NSSM
+    ///     auto-bounces the service when the game process exits. Probing
+    ///     <c>systemctl</c> on Windows wastes ~5s on every restart click and
+    ///     was the trigger for a cascading crash on a live prod box (the
+    ///     fallback shutdown ran concurrent with a stuck main-thread op and
+    ///     snowballed into a stack overflow).
+    ///
+    /// Kept as a pure function over <c>isWindows</c> so tests don't need a
+    /// real OS check or any DI plumbing.
+    /// </summary>
+    public static class OsRestartStrategy
+    {
+        public enum Kind
+        {
+            /// <summary>Try systemctl first, then fall back to in-game shutdown.</summary>
+            SystemctlThenInGameShutdown,
+
+            /// <summary>Skip the systemctl probe entirely; rely on the service
+            /// supervisor (NSSM <c>AppExit Restart</c>) to bounce the game
+            /// after the in-game shutdown exits the process.</summary>
+            InGameShutdownOnly,
+        }
+
+        /// <summary>
+        /// Pick a strategy based on whether the host is Windows.
+        /// </summary>
+        public static Kind Decide(bool isWindows)
+        {
+            return isWindows ? Kind.InGameShutdownOnly : Kind.SystemctlThenInGameShutdown;
+        }
+
+        /// <summary>
+        /// Convenience: decide based on the running host (uses <see cref="PlatformHelper.IsWindows"/>).
+        /// </summary>
+        public static Kind DecideForCurrentHost()
+        {
+            return Decide(PlatformHelper.IsWindows);
+        }
+    }
+}
diff --git a/src/KitsuneCommand/Web/Controllers/ServerController.cs b/src/KitsuneCommand/Web/Controllers/ServerController.cs
index 6f35b18..efa9cd9 100644
--- a/src/KitsuneCommand/Web/Controllers/ServerController.cs
+++ b/src/KitsuneCommand/Web/Controllers/ServerController.cs
@@ -218,13 +218,21 @@ public IHttpActionResult Shutdown([FromBody] ShutdownRequest request)
         }
 
         /// <summary>
-        /// Restart the server. Two-step:
-        ///   1. Try `sudo -n systemctl restart 7daystodie.service` (non-interactive).
-        ///      Works if install-linux-updater.sh has been run (adds the sudoers entry).
-        ///   2. If systemctl fails, fall back to in-game shutdown with a short delay.
-        ///      This relies on systemd having `Restart=always` configured to bounce it.
+        /// Restart the server. OS-aware:
+        ///   - Linux: try `sudo -n systemctl restart 7daystodie.service` first
+        ///     (works if install-linux-updater.sh has been run to add the
+        ///     sudoers entry). If that fails, fall back to in-game shutdown
+        ///     and rely on systemd `Restart=always` to bounce the service.
+        ///   - Windows: skip the systemctl probe entirely — `systemctl`
+        ///     doesn't exist on Windows, so probing it just wastes ~5s and
+        ///     produces a misleading "systemctl failed" warning. Go straight
+        ///     to in-game shutdown; NSSM (the standard Windows service
+        ///     supervisor for 7DTD) ships with `AppExit Restart` as its
+        ///     default and auto-bounces the service when the game exits.
         ///
-        /// If neither path works, the server stays down - tell the admin to run the installer.
+        /// The strategy decision is delegated to <see cref="OsRestartStrategy"/>
+        /// so it stays testable and shareable with any other restart entry
+        /// point (e.g. krestart) we add later.
         /// </summary>
         [HttpPost]
         [Route("restart")]
@@ -236,15 +244,29 @@ public IHttpActionResult Restart([FromBody] RestartRequest request)
             if (!System.Text.RegularExpressions.Regex.IsMatch(serviceName, @"^[a-zA-Z0-9._-]+$"))
                 return BadRequest("Invalid service name.");
 
-            // Try systemctl first (Linux path).
-            if (TryStart("sudo", $"-n systemctl restart {serviceName}", out var stderr, 5000))
+            var strategy = OsRestartStrategy.DecideForCurrentHost();
+
+            if (strategy == OsRestartStrategy.Kind.SystemctlThenInGameShutdown)
             {
-                return Ok(ApiResponse.Ok($"Restart triggered via systemctl ({serviceName}). Server bouncing."));
-            }
+                // Try systemctl first (Linux path).
+                if (TryStart("sudo", $"-n systemctl restart {serviceName}", out var stderr, 5000))
+                {
+                    return Ok(ApiResponse.Ok($"Restart triggered via systemctl ({serviceName}). Server bouncing."));
+                }
 
-            global::Log.Warning($"[KitsuneCommand] systemctl restart failed or not available ({stderr}). Falling back to in-game shutdown.");
+                global::Log.Warning($"[KitsuneCommand] systemctl restart failed or not available ({stderr}). Falling back to in-game shutdown.");
+            }
+            else
+            {
+                // Windows: NSSM (AppExit Restart) handles the bounce after the
+                // game process exits. INFO log so the operator sees we *chose*
+                // this path rather than failed into it.
+                global::Log.Out("[KitsuneCommand] Windows install detected; using in-game shutdown + service-supervisor restart (NSSM AppExit Restart).");
+            }
 
-            // Fallback: in-game shutdown with short delay, rely on systemd Restart=always.
+            // Common path: in-game shutdown with short delay. On Linux this is
+            // the fallback after systemctl failed; on Windows it's the only
+            // path we take.
             ModEntry.MainThreadContext.Post(_ =>
             {
                 try
@@ -253,10 +275,15 @@ public IHttpActionResult Restart([FromBody] RestartRequest request)
                 }
                 catch (Exception ex)
                 {
-                    global::Log.Error($"[KitsuneCommand] Fallback shutdown command failed: {ex.Message}");
+                    global::Log.Error($"[KitsuneCommand] In-game shutdown command failed: {ex.Message}");
                 }
             }, null);
 
+            if (strategy == OsRestartStrategy.Kind.InGameShutdownOnly)
+            {
+                return Ok(ApiResponse.Ok("Restart requested via in-game shutdown (5s delay). The Windows service supervisor (NSSM) will auto-bounce 7DTD when the game exits, provided AppExit Restart is configured (the NSSM default)."));
+            }
+
             return Ok(ApiResponse.Ok("Restart requested via in-game shutdown (5s delay). If systemd Restart=always is not set, server will stay down - run scripts/linux-updater/install-linux-updater.sh to configure."));
         }