diff --git a/pkg/middleware/middleware.go b/pkg/middleware/middleware.go
index 75da4c3ac27..92f97a0529b 100644
--- a/pkg/middleware/middleware.go
+++ b/pkg/middleware/middleware.go
@@ -1,6 +1,7 @@
 package middleware
 
 import (
+	"context"
 	"fmt"
 	"net/url"
 	"strconv"
@@ -228,7 +229,19 @@ func initContextWithToken(authTokenService models.UserTokenService, ctx *models.
 
 	// Rotate the token just before we write response headers to ensure there is no delay between
 	// the new token being generated and the client receiving it.
-	ctx.Resp.Before(func(w macaron.ResponseWriter) {
+	ctx.Resp.Before(rotateEndOfRequestFunc(ctx, authTokenService, token))
+
+	return true
+}
+
+func rotateEndOfRequestFunc(ctx *models.ReqContext, authTokenService models.UserTokenService, token *models.UserToken) macaron.BeforeFunc {
+	return func(w macaron.ResponseWriter) {
+		// if the request is cancelled by the client we should not try
+		// to rotate the token since the client would not accept any result.
+		if ctx.Context.Req.Context().Err() == context.Canceled {
+			return
+		}
+
 		rotated, err := authTokenService.TryRotateToken(ctx.Req.Context(), token, ctx.RemoteAddr(), ctx.Req.UserAgent())
 		if err != nil {
 			ctx.Logger.Error("Failed to rotate token", "error", err)
@@ -238,9 +251,7 @@ func initContextWithToken(authTokenService models.UserTokenService, ctx *models.
 		if rotated {
 			WriteSessionCookie(ctx, token.UnhashedToken, setting.LoginMaxLifetimeDays)
 		}
-	})
-
-	return true
+	}
 }
 
 func WriteSessionCookie(ctx *models.ReqContext, value string, maxLifetimeDays int) {
diff --git a/pkg/middleware/middleware_test.go b/pkg/middleware/middleware_test.go
index 1977eb66d28..dd91f58e7ef 100644
--- a/pkg/middleware/middleware_test.go
+++ b/pkg/middleware/middleware_test.go
@@ -6,16 +6,19 @@ import (
 	"errors"
 	"fmt"
 	"net/http"
+	"net/http/httptest"
 	"path/filepath"
 	"testing"
 	"time"
 
 	. "github.com/smartystreets/goconvey/convey"
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 	"gopkg.in/macaron.v1"
 
 	"github.com/grafana/grafana/pkg/api/dtos"
 	"github.com/grafana/grafana/pkg/bus"
+	"github.com/grafana/grafana/pkg/infra/log"
 	"github.com/grafana/grafana/pkg/infra/remotecache"
 	authproxy "github.com/grafana/grafana/pkg/middleware/auth_proxy"
 	"github.com/grafana/grafana/pkg/models"
@@ -541,7 +544,8 @@ func middlewareScenario(t *testing.T, desc string, fn scenarioFunc) {
 
 		sc := &scenarioContext{}
 
-		viewsPath, _ := filepath.Abs("../../public/views")
+		viewsPath, err := filepath.Abs("../../public/views")
+		require.NoError(t, err)
 
 		sc.m = macaron.New()
 		sc.m.Use(AddDefaultResponseHeaders())
@@ -571,3 +575,88 @@ func middlewareScenario(t *testing.T, desc string, fn scenarioFunc) {
 		fn(sc)
 	})
 }
+
+func TestDontRotateTokensOnCancelledRequests(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	reqContext, _, err := initTokenRotationTest(ctx)
+	require.NoError(t, err)
+
+	tryRotateCallCount := 0
+	uts := &auth.FakeUserAuthTokenService{
+		TryRotateTokenProvider: func(ctx context.Context, token *models.UserToken, clientIP, userAgent string) (bool, error) {
+			tryRotateCallCount++
+			return false, nil
+		},
+	}
+
+	token := &models.UserToken{AuthToken: "oldtoken"}
+
+	fn := rotateEndOfRequestFunc(reqContext, uts, token)
+	cancel()
+	fn(reqContext.Resp)
+
+	assert.Equal(t, 0, tryRotateCallCount, "Token rotation was attempted")
+}
+
+func TestTokenRotationAtEndOfRequest(t *testing.T) {
+	reqContext, rr, err := initTokenRotationTest(context.Background())
+	require.NoError(t, err)
+
+	uts := &auth.FakeUserAuthTokenService{
+		TryRotateTokenProvider: func(ctx context.Context, token *models.UserToken, clientIP, userAgent string) (bool, error) {
+			newToken, err := util.RandomHex(16)
+			require.NoError(t, err)
+			token.AuthToken = newToken
+			return true, nil
+		},
+	}
+
+	token := &models.UserToken{AuthToken: "oldtoken"}
+
+	rotateEndOfRequestFunc(reqContext, uts, token)(reqContext.Resp)
+
+	foundLoginCookie := false
+	for _, c := range rr.Result().Cookies() {
+		if c.Name == "login_token" {
+			foundLoginCookie = true
+
+			require.NotEqual(t, token.AuthToken, c.Value, "Auth token is still the same")
+		}
+	}
+
+	assert.True(t, foundLoginCookie, "Could not find cookie")
+}
+
+func initTokenRotationTest(ctx context.Context) (*models.ReqContext, *httptest.ResponseRecorder, error) {
+	setting.LoginCookieName = "login_token"
+	setting.LoginMaxLifetimeDays = 7
+
+	rr := httptest.NewRecorder()
+	req, err := http.NewRequestWithContext(ctx, "", "", nil)
+	if err != nil {
+		return nil, nil, err
+	}
+	reqContext := &models.ReqContext{
+		Context: &macaron.Context{
+			Req: macaron.Request{
+				Request: req,
+			},
+		},
+		Logger: log.New("testlogger"),
+	}
+
+	mw := mockWriter{rr}
+	reqContext.Resp = mw
+
+	return reqContext, rr, nil
+}
+
+type mockWriter struct {
+	*httptest.ResponseRecorder
+}
+
+func (mw mockWriter) Flush()                    {}
+func (mw mockWriter) Status() int               { return 0 }
+func (mw mockWriter) Size() int                 { return 0 }
+func (mw mockWriter) Written() bool             { return false }
+func (mw mockWriter) Before(macaron.BeforeFunc) {}