diff --git a/web/web.go b/web/web.go
index 9955facab8..ee16d2004b 100644
--- a/web/web.go
+++ b/web/web.go
@@ -540,6 +540,10 @@ func (h *Handler) Run(ctx context.Context) error {
 		httpl   = m.Match(cmux.HTTP1Fast())
 		grpcSrv = grpc.NewServer()
 	)
+
+	// Prevent open connections to block the shutdown of the handler.
+	m.SetReadTimeout(h.options.ReadTimeout)
+
 	av2 := api_v2.New(
 		h.options.LocalStorage,
 		h.options.TSDBDir,
@@ -603,11 +607,27 @@ func (h *Handler) Run(ctx context.Context) error {
 		return e
 	case <-ctx.Done():
 		httpSrv.Shutdown(ctx)
-		grpcSrv.GracefulStop()
+		stopGRPCSrv(grpcSrv)
 		return nil
 	}
 }
 
+// stopGRPCSrv stops a given GRPC server. An attempt to stop the server
+// gracefully is made first. After 15s, the server to forced to stop.
+func stopGRPCSrv(srv *grpc.Server) {
+	stop := make(chan struct{})
+	go func() {
+		srv.GracefulStop()
+		close(stop)
+	}()
+
+	select {
+	case <-time.After(15 * time.Second):
+		srv.Stop()
+	case <-stop:
+	}
+}
+
 func (h *Handler) alerts(w http.ResponseWriter, r *http.Request) {
 
 	var groups []*rules.Group
diff --git a/web/web_test.go b/web/web_test.go
index 96c4c5c4f5..a721e3050e 100644
--- a/web/web_test.go
+++ b/web/web_test.go
@@ -17,6 +17,7 @@ import (
 	"context"
 	"fmt"
 	"io/ioutil"
+	"net"
 	"net/http"
 	"net/http/httptest"
 	"net/url"
@@ -138,8 +139,10 @@ func TestReadyAndHealthy(t *testing.T) {
 	webHandler.config = &config.Config{}
 	webHandler.notifier = &notifier.Manager{}
 
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
 	go func() {
-		err := webHandler.Run(context.Background())
+		err := webHandler.Run(ctx)
 		if err != nil {
 			panic(fmt.Sprintf("Can't start web handler:%s", err))
 		}
@@ -323,8 +326,10 @@ func TestRoutePrefix(t *testing.T) {
 	opts.Flags = map[string]string{}
 
 	webHandler := New(nil, opts)
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
 	go func() {
-		err := webHandler.Run(context.Background())
+		err := webHandler.Run(ctx)
 		if err != nil {
 			panic(fmt.Sprintf("Can't start web handler:%s", err))
 		}
@@ -459,3 +464,73 @@ func TestHTTPMetrics(t *testing.T) {
 	testutil.Equals(t, 2, int(prom_testutil.ToFloat64(counter.WithLabelValues("/-/ready", strconv.Itoa(http.StatusOK)))))
 	testutil.Equals(t, 1, int(prom_testutil.ToFloat64(counter.WithLabelValues("/-/ready", strconv.Itoa(http.StatusServiceUnavailable)))))
 }
+
+func TestShutdownWithStaleConnection(t *testing.T) {
+	dbDir, err := ioutil.TempDir("", "tsdb-ready")
+	testutil.Ok(t, err)
+	defer testutil.Ok(t, os.RemoveAll(dbDir))
+
+	db, err := tsdb.Open(dbDir, nil, nil, nil)
+	testutil.Ok(t, err)
+
+	timeout := 10 * time.Second
+
+	opts := &Options{
+		ListenAddress:  ":9090",
+		ReadTimeout:    timeout,
+		MaxConnections: 512,
+		Context:        nil,
+		Storage:        nil,
+		LocalStorage:   &dbAdapter{db},
+		TSDBDir:        dbDir,
+		QueryEngine:    nil,
+		ScrapeManager:  &scrape.Manager{},
+		RuleManager:    &rules.Manager{},
+		Notifier:       nil,
+		RoutePrefix:    "/",
+		ExternalURL: &url.URL{
+			Scheme: "http",
+			Host:   "localhost:9090",
+			Path:   "/",
+		},
+		Version:  &PrometheusVersion{},
+		Gatherer: prometheus.DefaultGatherer,
+	}
+
+	opts.Flags = map[string]string{}
+
+	webHandler := New(nil, opts)
+
+	webHandler.config = &config.Config{}
+	webHandler.notifier = &notifier.Manager{}
+
+	closed := make(chan struct{})
+
+	ctx, cancel := context.WithCancel(context.Background())
+	go func() {
+		err := webHandler.Run(ctx)
+		if err != nil {
+			panic(fmt.Sprintf("Can't start web handler:%s", err))
+		}
+		close(closed)
+	}()
+
+	// Give some time for the web goroutine to run since we need the server
+	// to be up before starting tests.
+	time.Sleep(5 * time.Second)
+
+	// Open a socket, and don't use it. This connection should then be closed
+	// after the ReadTimeout.
+	c, err := net.Dial("tcp", "localhost:9090")
+	testutil.Ok(t, err)
+	t.Cleanup(func() { testutil.Ok(t, c.Close()) })
+
+	// Stop the web handler.
+	cancel()
+
+	select {
+	case <-closed:
+	case <-time.After(timeout + 5*time.Second):
+		t.Fatalf("Server still running after read timeout.")
+	}
+}