diff --git a/pkg/windows/service/BUILD b/pkg/windows/service/BUILD
index e64c40488b4..e518a527080 100644
--- a/pkg/windows/service/BUILD
+++ b/pkg/windows/service/BUILD
@@ -11,6 +11,7 @@ go_library(
     importpath = "k8s.io/kubernetes/pkg/windows/service",
     deps = select({
         "@io_bazel_rules_go//go/platform:windows": [
+            "//staging/src/k8s.io/apiserver/pkg/server:go_default_library",
             "//vendor/golang.org/x/sys/windows:go_default_library",
             "//vendor/golang.org/x/sys/windows/svc:go_default_library",
             "//vendor/k8s.io/klog:go_default_library",
diff --git a/pkg/windows/service/service.go b/pkg/windows/service/service.go
index a5bffa1822e..47961b842ef 100644
--- a/pkg/windows/service/service.go
+++ b/pkg/windows/service/service.go
@@ -20,7 +20,9 @@ package service
 
 import (
 	"os"
+	"time"
 
+	"k8s.io/apiserver/pkg/server"
 	"k8s.io/klog"
 
 	"golang.org/x/sys/windows"
@@ -80,9 +82,31 @@ Loop:
 			case svc.Interrogate:
 				s <- c.CurrentStatus
 			case svc.Stop, svc.Shutdown:
-				s <- svc.Status{State: svc.Stopped}
-				// TODO: Stop the kubelet gracefully instead of killing the process
-				os.Exit(0)
+				klog.Infof("Service stopping")
+				// We need to translate this request into a signal that can be handled by the the signal handler
+				// handling shutdowns normally (currently apiserver/pkg/server/signal.go).
+				// If we do not do this, our main threads won't be notified of the upcoming shutdown.
+				// Since Windows services do not use any console, we cannot simply generate a CTRL_BREAK_EVENT
+				// but need a dedicated notification mechanism.
+				graceful := server.RequestShutdown()
+
+				// Free up the control handler and let us terminate as gracefully as possible.
+				// If that takes too long, the service controller will kill the remaining threads.
+				// As per https://docs.microsoft.com/en-us/windows/desktop/services/service-control-handler-function
+				s <- svc.Status{State: svc.StopPending}
+
+				// If we cannot exit gracefully, we really only can exit our process, so atleast the
+				// service manager will think that we gracefully exited. At the time of writing this comment this is
+				// needed for applications that do not use signals (e.g. kube-proxy)
+				if !graceful {
+					go func() {
+						// Ensure the SCM was notified (The operation above (send to s) was received and communicated to the
+						// service control manager - so it doesn't look like the service crashes)
+						time.Sleep(1 * time.Second)
+						os.Exit(0)
+					}()
+				}
+				break Loop
 			}
 		}
 	}
diff --git a/staging/src/k8s.io/apiserver/pkg/server/signal.go b/staging/src/k8s.io/apiserver/pkg/server/signal.go
index 6f0cff4baed..0ea19d6606d 100644
--- a/staging/src/k8s.io/apiserver/pkg/server/signal.go
+++ b/staging/src/k8s.io/apiserver/pkg/server/signal.go
@@ -22,6 +22,7 @@ import (
 )
 
 var onlyOneSignalHandler = make(chan struct{})
+var shutdownHandler chan os.Signal
 
 // SetupSignalHandler registered for SIGTERM and SIGINT. A stop channel is returned
 // which is closed on one of these signals. If a second signal is caught, the program
@@ -29,15 +30,30 @@ var onlyOneSignalHandler = make(chan struct{})
 func SetupSignalHandler() <-chan struct{} {
 	close(onlyOneSignalHandler) // panics when called twice
 
+	shutdownHandler = make(chan os.Signal, 2)
+
 	stop := make(chan struct{})
-	c := make(chan os.Signal, 2)
-	signal.Notify(c, shutdownSignals...)
+	signal.Notify(shutdownHandler, shutdownSignals...)
 	go func() {
-		<-c
+		<-shutdownHandler
 		close(stop)
-		<-c
+		<-shutdownHandler
 		os.Exit(1) // second signal. Exit directly.
 	}()
 
 	return stop
 }
+
+// RequestShutdown emulates a received event that is considered as shutdown signal (SIGTERM/SIGINT)
+// This returns whether a handler was notified
+func RequestShutdown() bool {
+	if shutdownHandler != nil {
+		select {
+		case shutdownHandler <- shutdownSignals[0]:
+			return true
+		default:
+		}
+	}
+
+	return false
+}