diff --git a/staging/src/k8s.io/apiserver/pkg/server/genericapiserver_graceful_termination_test.go b/staging/src/k8s.io/apiserver/pkg/server/genericapiserver_graceful_termination_test.go
new file mode 100644
index 00000000000..7c30add2203
--- /dev/null
+++ b/staging/src/k8s.io/apiserver/pkg/server/genericapiserver_graceful_termination_test.go
@@ -0,0 +1,404 @@
+/*
+Copyright 2021 The Kubernetes Authors.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+package server
+
+import (
+	"context"
+	"crypto/tls"
+	"crypto/x509"
+	"fmt"
+	"io/ioutil"
+	"log"
+	"net"
+	"net/http"
+	"net/http/httptrace"
+	"reflect"
+	"sync"
+	"testing"
+	"time"
+
+	"k8s.io/apimachinery/pkg/util/wait"
+	genericapifilters "k8s.io/apiserver/pkg/endpoints/filters"
+	"k8s.io/apiserver/pkg/server/dynamiccertificates"
+	genericfilters "k8s.io/apiserver/pkg/server/filters"
+
+	"github.com/google/go-cmp/cmp"
+	"golang.org/x/net/http2"
+)
+
+// doer sends a request to the server
+type doer func(client *http.Client, gci func(httptrace.GotConnInfo), path string, timeout time.Duration) result
+
+func (d doer) Do(client *http.Client, gci func(httptrace.GotConnInfo), path string, timeout time.Duration) result {
+	return d(client, gci, path, timeout)
+}
+
+type result struct {
+	err      error
+	response *http.Response
+}
+
+// wrap a terminationSignal so the test can inject its own callback
+type wrappedTerminationSignal struct {
+	terminationSignal
+	callback func(bool, string, terminationSignal)
+}
+
+func (w *wrappedTerminationSignal) Signal() {
+	var name string
+	if ncw, ok := w.terminationSignal.(*namedChannelWrapper); ok {
+		name = ncw.name
+	}
+
+	// the callback is invoked before and after the termination event is signaled
+	if w.callback != nil {
+		w.callback(true, name, w.terminationSignal)
+	}
+	w.terminationSignal.Signal()
+	if w.callback != nil {
+		w.callback(false, name, w.terminationSignal)
+	}
+}
+
+func wrapTerminationSignals(t *testing.T, ts *terminationSignals, callback func(bool, string, terminationSignal)) {
+	newWrappedTerminationSignal := func(delegated terminationSignal) terminationSignal {
+		return &wrappedTerminationSignal{
+			terminationSignal: delegated,
+			callback:          callback,
+		}
+	}
+
+	ts.AfterShutdownDelayDuration = newWrappedTerminationSignal(ts.AfterShutdownDelayDuration)
+	ts.HTTPServerStoppedListening = newWrappedTerminationSignal(ts.HTTPServerStoppedListening)
+	ts.InFlightRequestsDrained = newWrappedTerminationSignal(ts.InFlightRequestsDrained)
+	ts.ShutdownInitiated = newWrappedTerminationSignal(ts.ShutdownInitiated)
+}
+
+type step struct {
+	waitCh, doneCh chan struct{}
+	fn             func()
+}
+
+func (s step) done() <-chan struct{} {
+	close(s.waitCh)
+	return s.doneCh
+}
+func (s step) execute() {
+	defer close(s.doneCh)
+	<-s.waitCh
+	s.fn()
+}
+func newStep(fn func()) *step {
+	return &step{
+		fn:     fn,
+		waitCh: make(chan struct{}),
+		doneCh: make(chan struct{}),
+	}
+}
+
+func TestGracefulTerminationWithKeepListeningDuringGracefulTerminationDisabled(t *testing.T) {
+	s := newGenericAPIServer(t)
+
+	// record the termination events in the order they are signaled
+	var signalOrderLock sync.Mutex
+	signalOrderGot := make([]string, 0)
+	recordOrderFn := func(before bool, name string, e terminationSignal) {
+		if !before {
+			return
+		}
+		signalOrderLock.Lock()
+		defer signalOrderLock.Unlock()
+		signalOrderGot = append(signalOrderGot, name)
+	}
+
+	// handler for a request that we want to keep in flight through to the end
+	inFlightRequestBlockedCh, inFlightStartedCh := make(chan result), make(chan struct{})
+	inFlightRequest := http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+		close(inFlightStartedCh)
+		// this request handler blocks until we deliberately unblock it.
+		<-inFlightRequestBlockedCh
+		w.WriteHeader(http.StatusOK)
+	})
+	s.Handler.NonGoRestfulMux.Handle("/in-flight-request-as-designed", inFlightRequest)
+
+	connReusingClient := newClient(false)
+	doer := setupDoer(t, s.SecureServingInfo)
+
+	var delayedStopVerificationStepExecuted bool
+	delayedStopVerificationStep := newStep(func() {
+		delayedStopVerificationStepExecuted = true
+		t.Log("Before ShutdownDelayDuration elapses new request(s) should be served")
+		resultGot := doer.Do(connReusingClient, shouldReuseConnection(t), "/echo?message=request-on-an-existing-connection-should-succeed", time.Second)
+		requestMustSucceed(t, resultGot)
+		resultGot = doer.Do(newClient(true), shouldUseNewConnection(t), "/echo?message=request-on-a-new-tcp-connection-should-succeed", time.Second)
+		requestMustSucceed(t, resultGot)
+	})
+	steps := func(before bool, name string, e terminationSignal) {
+		// Before AfterShutdownDelayDuration event is signaled, the test
+		// will send request(s) to assert on expected behavior.
+		if name == "AfterShutdownDelayDuration" && before {
+			// it unblocks the verification step and waits for it to complete
+			<-delayedStopVerificationStep.done()
+		}
+	}
+
+	// wrap the termination signals of the GenericAPIServer so the test can inject its own callback
+	wrapTerminationSignals(t, &s.terminationSignals, func(before bool, name string, e terminationSignal) {
+		recordOrderFn(before, name, e)
+		steps(before, name, e)
+	})
+
+	// start the API server
+	stopCh, runCompletedCh := make(chan struct{}), make(chan struct{})
+	go func() {
+		defer close(runCompletedCh)
+		s.PrepareRun().Run(stopCh)
+	}()
+	waitForAPIServerStarted(t, doer)
+
+	// step 1: fire a request that we want to keep in-flight through to the end
+	inFlightResultCh := make(chan result)
+	go func() {
+		resultGot := doer.Do(connReusingClient, func(httptrace.GotConnInfo) {}, "/in-flight-request-as-designed", 0)
+		inFlightResultCh <- resultGot
+	}()
+	select {
+	case <-inFlightStartedCh:
+	case <-time.After(5 * time.Second):
+		t.Fatalf("Waited for 5s for the in-flight request to reach the server")
+	}
+
+	// step 2: signal termination event: initiate a shutdown
+	close(stopCh)
+
+	// step 3: before ShutdownDelayDuration elapses new request(s) should be served successfully.
+	delayedStopVerificationStep.execute()
+	if !delayedStopVerificationStepExecuted {
+		t.Fatal("Expected the AfterShutdownDelayDuration verification step to execute")
+	}
+
+	// step 4: wait for the HTTP Server listener to have stopped
+	httpServerStoppedListeningCh := s.terminationSignals.HTTPServerStoppedListening
+	select {
+	case <-httpServerStoppedListeningCh.Signaled():
+	case <-time.After(5 * time.Second):
+		t.Fatal("Expected the server to signal HTTPServerStoppedListening event")
+	}
+
+	// step 5: the server has stopped listening but we still have a request
+	// in flight, let it unblock and we expect the request to succeed.
+	close(inFlightRequestBlockedCh)
+	var inFlightResultGot result
+	select {
+	case inFlightResultGot = <-inFlightResultCh:
+	case <-time.After(5 * time.Second):
+		t.Fatal("Expected the server to send a response")
+	}
+	requestMustSucceed(t, inFlightResultGot)
+
+	t.Log("Waiting for the apiserver Run method to return")
+	select {
+	case <-runCompletedCh:
+	case <-time.After(5 * time.Second):
+		t.Fatal("Expected the apiserver Run method to return")
+	}
+
+	terminationSignalOrderExpected := []string{
+		string("ShutdownInitiated"),
+		string("AfterShutdownDelayDuration"),
+		string("HTTPServerStoppedListening"),
+		string("InFlightRequestsDrained"),
+	}
+	func() {
+		signalOrderLock.Lock()
+		defer signalOrderLock.Unlock()
+		if !reflect.DeepEqual(terminationSignalOrderExpected, signalOrderGot) {
+			t.Errorf("Expected order of termination event signal to match, diff: %s", cmp.Diff(terminationSignalOrderExpected, signalOrderGot))
+		}
+	}()
+}
+
+func shouldReuseConnection(t *testing.T) func(httptrace.GotConnInfo) {
+	return func(ci httptrace.GotConnInfo) {
+		if !ci.Reused {
+			t.Errorf("Expected the request to use an existing TCP connection, but got: %+v", ci)
+		}
+	}
+}
+
+func shouldUseNewConnection(t *testing.T) func(httptrace.GotConnInfo) {
+	return func(ci httptrace.GotConnInfo) {
+		if ci.Reused {
+			t.Errorf("Expected the request to use a new TCP connection, but got: %+v", ci)
+		}
+	}
+}
+
+func requestMustSucceed(t *testing.T, resultGot result) {
+	if resultGot.err != nil {
+		t.Errorf("Expected no error, but got: %v", resultGot.err)
+		return
+	}
+	if resultGot.response.StatusCode != http.StatusOK {
+		t.Errorf("Expected Status Code: %d, but got: %d", http.StatusOK, resultGot.response.StatusCode)
+	}
+}
+
+func waitForAPIServerStarted(t *testing.T, doer doer) {
+	client := newClient(true)
+	i := 1
+	err := wait.PollImmediate(100*time.Millisecond, 5*time.Second, func() (done bool, err error) {
+		result := doer.Do(client, func(httptrace.GotConnInfo) {}, fmt.Sprintf("/echo?message=attempt-%d", i), 100*time.Millisecond)
+		i++
+
+		if result.err != nil {
+			t.Logf("Still waiting for the server to start - err: %v", err)
+			return false, nil
+		}
+		if result.response.StatusCode != http.StatusOK {
+			t.Logf("Still waiting for the server to start - expecting: %d, but got: %v", http.StatusOK, result.response)
+			return false, nil
+		}
+
+		t.Log("The API server has started")
+		return true, nil
+	})
+
+	if err != nil {
+		t.Fatalf("The server has failed to start - err: %v", err)
+	}
+}
+
+func setupDoer(t *testing.T, info *SecureServingInfo) doer {
+	_, port, err := info.HostPort()
+	if err != nil {
+		t.Fatalf("Expected host, port from SecureServingInfo, but got: %v", err)
+	}
+
+	return func(client *http.Client, callback func(httptrace.GotConnInfo), path string, timeout time.Duration) result {
+		url := fmt.Sprintf("https://%s:%d%s", "127.0.0.1", port, path)
+		t.Logf("Sending request - timeout: %s, url: %s", timeout, url)
+
+		req, err := http.NewRequest("GET", url, nil)
+		if err != nil {
+			return result{response: nil, err: err}
+		}
+
+		// setup request timeout
+		var ctx context.Context
+		if timeout > 0 {
+			var cancel context.CancelFunc
+			ctx, cancel = context.WithTimeout(req.Context(), timeout)
+			defer cancel()
+
+			req = req.WithContext(ctx)
+		}
+
+		// setup trace
+		trace := &httptrace.ClientTrace{
+			GotConn: func(connInfo httptrace.GotConnInfo) {
+				callback(connInfo)
+			},
+		}
+		req = req.WithContext(httptrace.WithClientTrace(req.Context(), trace))
+
+		response, err := client.Do(req)
+		// in this test, we don't depend on the body of the response, so we can
+		// close the Body here to ensure the underlying transport can be reused
+		if response != nil {
+			ioutil.ReadAll(response.Body)
+			response.Body.Close()
+		}
+		return result{
+			err:      err,
+			response: response,
+		}
+	}
+}
+
+func newClient(useNewConnection bool) *http.Client {
+	clientCACertPool := x509.NewCertPool()
+	clientCACertPool.AppendCertsFromPEM(backendCrt)
+	tlsConfig := &tls.Config{
+		RootCAs:    clientCACertPool,
+		NextProtos: []string{http2.NextProtoTLS},
+	}
+
+	tr := &http.Transport{
+		TLSClientConfig:   tlsConfig,
+		DisableKeepAlives: useNewConnection,
+	}
+	if err := http2.ConfigureTransport(tr); err != nil {
+		log.Fatalf("Failed to configure HTTP2 transport: %v", err)
+	}
+	return &http.Client{
+		Timeout:   0,
+		Transport: tr,
+	}
+}
+
+func newGenericAPIServer(t *testing.T) *GenericAPIServer {
+	config, _ := setUp(t)
+	config.ShutdownDelayDuration = 100 * time.Millisecond
+	config.BuildHandlerChainFunc = func(apiHandler http.Handler, c *Config) http.Handler {
+		handler := genericfilters.WithWaitGroup(apiHandler, c.LongRunningFunc, c.HandlerChainWaitGroup)
+		handler = genericapifilters.WithRequestInfo(handler, c.RequestInfoResolver)
+		return handler
+	}
+
+	s, err := config.Complete(nil).New("test", NewEmptyDelegate())
+	if err != nil {
+		t.Fatalf("Error in bringing up the server: %v", err)
+	}
+
+	ln, err := net.Listen("tcp", "0.0.0.0:0")
+	if err != nil {
+		t.Fatalf("failed to listen on %v: %v", "0.0.0.0:0", err)
+	}
+	s.SecureServingInfo = &SecureServingInfo{}
+	s.SecureServingInfo.Listener = &wrappedListener{ln, t}
+
+	cert, err := dynamiccertificates.NewStaticCertKeyContent("serving-cert", backendCrt, backendKey)
+	if err != nil {
+		t.Fatalf("failed to load cert - %v", err)
+	}
+	s.SecureServingInfo.Cert = cert
+
+	// we use this handler to send a test request to the server.
+	s.Handler.NonGoRestfulMux.Handle("/echo", http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+		t.Logf("[server] received a request, proto: %s, url: %s", req.Proto, req.RequestURI)
+
+		w.Header().Add("echo", req.URL.Query().Get("message"))
+		w.WriteHeader(http.StatusOK)
+	}))
+
+	return s
+}
+
+type wrappedListener struct {
+	net.Listener
+	t *testing.T
+}
+
+func (ln wrappedListener) Accept() (net.Conn, error) {
+	c, err := ln.Listener.Accept()
+
+	if tc, ok := c.(*net.TCPConn); ok {
+		ln.t.Logf("[server] seen new connection: %#v", tc)
+	}
+	return c, err
+}