diff --git a/main.go b/main.go
index cf7e964c..c3877bce 100644
--- a/main.go
+++ b/main.go
@@ -1,9 +1,12 @@
 package main
 
 import (
+	"context"
 	"fmt"
 	"os"
+	"os/signal"
 	"runtime"
+	"syscall"
 
 	"github.com/ghodss/yaml"
 	"github.com/oauth2-proxy/oauth2-proxy/v7/pkg/apis/options"
@@ -54,12 +57,23 @@ func main() {
 	}
 
 	validator := NewValidator(opts.EmailDomains, opts.AuthenticatedEmailsFile)
-	oauthproxy, err := NewOAuthProxy(opts, validator)
+
+	ctx, cancelFunc := context.WithCancel(context.Background())
+
+	// Observe signals in background goroutine.
+	go func() {
+		sigint := make(chan os.Signal, 1)
+		signal.Notify(sigint, os.Interrupt, syscall.SIGTERM)
+		<-sigint
+		cancelFunc() // cancel the context
+	}()
+
+	oauthproxy, err := NewOAuthProxy(ctx, opts, validator)
 	if err != nil {
 		logger.Fatalf("ERROR: Failed to initialise OAuth2 Proxy: %v", err)
 	}
 
-	if err := oauthproxy.Start(); err != nil {
+	if err := oauthproxy.Start(ctx); err != nil {
 		logger.Fatalf("ERROR: Failed to start OAuth2 Proxy: %v", err)
 	}
 }
diff --git a/oauthproxy.go b/oauthproxy.go
index b85c89b4..8439e1ce 100644
--- a/oauthproxy.go
+++ b/oauthproxy.go
@@ -10,11 +10,8 @@ import (
 	"net"
 	"net/http"
 	"net/url"
-	"os"
-	"os/signal"
 	"regexp"
 	"strings"
-	"syscall"
 	"time"
 
 	"github.com/gorilla/mux"
@@ -117,7 +114,7 @@ type OAuthProxy struct {
 }
 
 // NewOAuthProxy creates a new instance of OAuthProxy from the options provided
-func NewOAuthProxy(opts *options.Options, validator func(string) bool) (*OAuthProxy, error) {
+func NewOAuthProxy(ctx context.Context, opts *options.Options, validator func(string) bool) (*OAuthProxy, error) {
 	sessionStore, err := sessions.NewSessionStore(&opts.Session, &opts.Cookie)
 	if err != nil {
 		return nil, fmt.Errorf("error initialising session store: %v", err)
@@ -200,7 +197,7 @@ func NewOAuthProxy(opts *options.Options, validator func(string) bool) (*OAuthPr
 		return nil, err
 	}
 
-	preAuthChain, err := buildPreAuthChain(opts, sessionStore)
+	preAuthChain, err := buildPreAuthChain(ctx, opts, sessionStore)
 	if err != nil {
 		return nil, fmt.Errorf("could not build pre-auth chain: %v", err)
 	}
@@ -258,23 +255,13 @@ func NewOAuthProxy(opts *options.Options, validator func(string) bool) (*OAuthPr
 	return p, nil
 }
 
-func (p *OAuthProxy) Start() error {
+func (p *OAuthProxy) Start(ctx context.Context) error {
 	if p.server == nil {
 		// We have to call setupServer before Start is called.
 		// If this doesn't happen it's a programming error.
 		panic("server has not been initialised")
 	}
 
-	ctx, cancel := context.WithCancel(context.Background())
-
-	// Observe signals in background goroutine.
-	go func() {
-		sigint := make(chan os.Signal, 1)
-		signal.Notify(sigint, os.Interrupt, syscall.SIGTERM)
-		<-sigint
-		cancel() // cancel the context
-	}()
-
 	return p.server.Start(ctx)
 }
 
@@ -284,6 +271,7 @@ func (p *OAuthProxy) setupServer(opts *options.Options) error {
 		BindAddress:       opts.Server.BindAddress,
 		SecureBindAddress: opts.Server.SecureBindAddress,
 		TLS:               opts.Server.TLS,
+		ShutdownDuration:  opts.ShutdownDuration,
 	}
 
 	// Option: AllowQuerySemicolons
@@ -353,7 +341,7 @@ func (p *OAuthProxy) buildProxySubrouter(s *mux.Router) {
 // buildPreAuthChain constructs a chain that should process every request before
 // the OAuth2 Proxy authentication logic kicks in.
 // For example forcing HTTPS or health checks.
-func buildPreAuthChain(opts *options.Options, sessionStore sessionsapi.SessionStore) (alice.Chain, error) {
+func buildPreAuthChain(ctx context.Context, opts *options.Options, sessionStore sessionsapi.SessionStore) (alice.Chain, error) {
 	chain := alice.New(middleware.NewScope(opts.ReverseProxy, opts.Logging.RequestIDHeader))
 
 	if opts.ForceHTTPS {
@@ -374,17 +362,18 @@ func buildPreAuthChain(opts *options.Options, sessionStore sessionsapi.SessionSt
 
 	// To silence logging of health checks, register the health check handler before
 	// the logging handler
+	readinessCheck := middleware.NewReadynessCheck(ctx, opts.ReadyPath, sessionStore)
 	if opts.Logging.SilencePing {
 		chain = chain.Append(
 			middleware.NewHealthCheck(healthCheckPaths, healthCheckUserAgents),
-			middleware.NewReadynessCheck(opts.ReadyPath, sessionStore),
+			readinessCheck,
 			middleware.NewRequestLogger(),
 		)
 	} else {
 		chain = chain.Append(
 			middleware.NewRequestLogger(),
 			middleware.NewHealthCheck(healthCheckPaths, healthCheckUserAgents),
-			middleware.NewReadynessCheck(opts.ReadyPath, sessionStore),
+			readinessCheck,
 		)
 	}
 
diff --git a/oauthproxy_test.go b/oauthproxy_test.go
index 488b8cea..0f0edbbd 100644
--- a/oauthproxy_test.go
+++ b/oauthproxy_test.go
@@ -47,7 +47,7 @@ func TestRobotsTxt(t *testing.T) {
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
 
-	proxy, err := NewOAuthProxy(opts, func(string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -108,7 +108,7 @@ func Test_redeemCode(t *testing.T) {
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
 
-	proxy, err := NewOAuthProxy(opts, func(string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -160,7 +160,7 @@ func Test_enrichSession(t *testing.T) {
 			err := validation.Validate(opts)
 			assert.NoError(t, err)
 
-			proxy, err := NewOAuthProxy(opts, func(string) bool { return true })
+			proxy, err := NewOAuthProxy(context.Background(), opts, func(string) bool { return true })
 			if err != nil {
 				t.Fatal(err)
 			}
@@ -229,7 +229,7 @@ func TestBasicAuthPassword(t *testing.T) {
 	providerURL, _ := url.Parse(providerServer.URL)
 	const emailAddress = "john.doe@example.com"
 
-	proxy, err := NewOAuthProxy(opts, func(email string) bool {
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(email string) bool {
 		return email == emailAddress
 	})
 	if err != nil {
@@ -291,7 +291,7 @@ func TestPassGroupsHeadersWithGroups(t *testing.T) {
 		CreatedAt:   &created,
 	}
 
-	proxy, err := NewOAuthProxy(opts, func(email string) bool {
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(email string) bool {
 		return email == emailAddress
 	})
 	assert.NoError(t, err)
@@ -387,7 +387,7 @@ func NewPassAccessTokenTest(opts PassAccessTokenTestOptions) (*PassAccessTokenTe
 
 	testProvider := NewTestProvider(providerURL, emailAddress)
 	testProvider.ValidToken = opts.ValidToken
-	patt.proxy, err = NewOAuthProxy(patt.opts, func(email string) bool {
+	patt.proxy, err = NewOAuthProxy(context.Background(), patt.opts, func(email string) bool {
 		return email == emailAddress
 	})
 	patt.proxy.provider = testProvider
@@ -592,7 +592,7 @@ func NewSignInPageTest(skipProvider bool) (*SignInPageTest, error) {
 		return nil, err
 	}
 
-	sipTest.proxy, err = NewOAuthProxy(sipTest.opts, func(email string) bool {
+	sipTest.proxy, err = NewOAuthProxy(context.Background(), sipTest.opts, func(email string) bool {
 		return true
 	})
 	if err != nil {
@@ -628,7 +628,7 @@ func TestManualSignInStoresUserGroupsInTheSession(t *testing.T) {
 		t.Fatal(err)
 	}
 
-	proxy, err := NewOAuthProxy(opts, func(email string) bool {
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(email string) bool {
 		return true
 	})
 	if err != nil {
@@ -676,7 +676,7 @@ func ManualSignInWithCredentials(t *testing.T, user, pass string) int {
 		t.Fatal(err)
 	}
 
-	proxy, err := NewOAuthProxy(opts, func(email string) bool {
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(email string) bool {
 		return true
 	})
 	if err != nil {
@@ -826,7 +826,7 @@ func NewProcessCookieTest(opts ProcessCookieTestOpts, modifiers ...OptionsModifi
 		return nil, err
 	}
 
-	pcTest.proxy, err = NewOAuthProxy(pcTest.opts, func(email string) bool {
+	pcTest.proxy, err = NewOAuthProxy(context.Background(), pcTest.opts, func(email string) bool {
 		return pcTest.validateUser
 	})
 	if err != nil {
@@ -1200,7 +1200,7 @@ func TestAuthOnlyEndpointSetXAuthRequestHeaders(t *testing.T) {
 	err := validation.Validate(pcTest.opts)
 	assert.NoError(t, err)
 
-	pcTest.proxy, err = NewOAuthProxy(pcTest.opts, func(email string) bool {
+	pcTest.proxy, err = NewOAuthProxy(context.Background(), pcTest.opts, func(email string) bool {
 		return pcTest.validateUser
 	})
 	if err != nil {
@@ -1293,7 +1293,7 @@ func TestAuthOnlyEndpointSetBasicAuthTrueRequestHeaders(t *testing.T) {
 	err := validation.Validate(pcTest.opts)
 	assert.NoError(t, err)
 
-	pcTest.proxy, err = NewOAuthProxy(pcTest.opts, func(email string) bool {
+	pcTest.proxy, err = NewOAuthProxy(context.Background(), pcTest.opts, func(email string) bool {
 		return pcTest.validateUser
 	})
 	if err != nil {
@@ -1373,7 +1373,7 @@ func TestAuthOnlyEndpointSetBasicAuthFalseRequestHeaders(t *testing.T) {
 	err := validation.Validate(pcTest.opts)
 	assert.NoError(t, err)
 
-	pcTest.proxy, err = NewOAuthProxy(pcTest.opts, func(email string) bool {
+	pcTest.proxy, err = NewOAuthProxy(context.Background(), pcTest.opts, func(email string) bool {
 		return pcTest.validateUser
 	})
 	if err != nil {
@@ -1429,7 +1429,7 @@ func TestAuthSkippedForPreflightRequests(t *testing.T) {
 
 	upstreamURL, _ := url.Parse(upstreamServer.URL)
 
-	proxy, err := NewOAuthProxy(opts, func(string) bool { return false })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(string) bool { return false })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -1554,7 +1554,7 @@ func (st *SignatureTest) MakeRequestWithExpectedKey(method, body, key string) er
 	if err != nil {
 		return err
 	}
-	proxy, err := NewOAuthProxy(st.opts, func(email string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), st.opts, func(email string) bool { return true })
 	if err != nil {
 		return err
 	}
@@ -1642,7 +1642,7 @@ func newAjaxRequestTest(forceJSONErrors bool) (*ajaxRequestTest, error) {
 		return nil, err
 	}
 
-	test.proxy, err = NewOAuthProxy(test.opts, func(email string) bool {
+	test.proxy, err = NewOAuthProxy(context.Background(), test.opts, func(email string) bool {
 		return true
 	})
 	if err != nil {
@@ -1958,7 +1958,7 @@ func Test_noCacheHeaders(t *testing.T) {
 	opts.SkipAuthRegex = []string{".*"}
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
-	proxy, err := NewOAuthProxy(opts, func(_ string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(_ string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -2233,7 +2233,7 @@ func TestTrustedIPs(t *testing.T) {
 			err := validation.Validate(opts)
 			assert.NoError(t, err)
 
-			proxy, err := NewOAuthProxy(opts, func(string) bool { return true })
+			proxy, err := NewOAuthProxy(context.Background(), opts, func(string) bool { return true })
 			assert.NoError(t, err)
 			rw := httptest.NewRecorder()
 
@@ -2478,7 +2478,7 @@ func TestApiRoutes(t *testing.T) {
 	opts.SkipProviderButton = true
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
-	proxy, err := NewOAuthProxy(opts, func(_ string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(_ string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -2561,7 +2561,7 @@ func TestAllowedRequest(t *testing.T) {
 	}
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
-	proxy, err := NewOAuthProxy(opts, func(_ string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(_ string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -2660,7 +2660,7 @@ func TestAllowedRequestWithForwardedUriHeader(t *testing.T) {
 	}
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
-	proxy, err := NewOAuthProxy(opts, func(_ string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(_ string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -2759,7 +2759,7 @@ func TestAllowedRequestNegateWithoutMethod(t *testing.T) {
 	}
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
-	proxy, err := NewOAuthProxy(opts, func(_ string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(_ string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -2859,7 +2859,7 @@ func TestAllowedRequestNegateWithMethod(t *testing.T) {
 	}
 	err := validation.Validate(opts)
 	assert.NoError(t, err)
-	proxy, err := NewOAuthProxy(opts, func(_ string) bool { return true })
+	proxy, err := NewOAuthProxy(context.Background(), opts, func(_ string) bool { return true })
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -3460,7 +3460,7 @@ func TestGetOAuthRedirectURI(t *testing.T) {
 			err := validation.Validate(baseOpts)
 			assert.NoError(t, err)
 
-			proxy, err := NewOAuthProxy(tt.setupOpts(baseOpts), func(string) bool { return true })
+			proxy, err := NewOAuthProxy(context.Background(), tt.setupOpts(baseOpts), func(string) bool { return true })
 			assert.NoError(t, err)
 
 			assert.Equalf(t, tt.want, proxy.getOAuthRedirectURI(tt.req), "getOAuthRedirectURI(%v)", tt.req)
diff --git a/pkg/apis/options/options.go b/pkg/apis/options/options.go
index 8fa72c7c..eef86f7e 100644
--- a/pkg/apis/options/options.go
+++ b/pkg/apis/options/options.go
@@ -3,6 +3,7 @@ package options
 import (
 	"crypto"
 	"net/url"
+	"time"
 
 	ipapi "github.com/oauth2-proxy/oauth2-proxy/v7/pkg/apis/ip"
 	internaloidc "github.com/oauth2-proxy/oauth2-proxy/v7/pkg/providers/oidc"
@@ -29,6 +30,8 @@ type Options struct {
 	RawRedirectURL      string   `flag:"redirect-url" cfg:"redirect_url"`
 	RelativeRedirectURL bool     `flag:"relative-redirect-url" cfg:"relative_redirect_url"`
 
+	ShutdownDuration time.Duration `flag:"shutdown-duration" cfg:"shutdown_duration"`
+
 	AuthenticatedEmailsFile string   `flag:"authenticated-emails-file" cfg:"authenticated_emails_file"`
 	EmailDomains            []string `flag:"email-domain" cfg:"email_domains"`
 	WhitelistDomains        []string `flag:"whitelist-domain" cfg:"whitelist_domains"`
@@ -161,6 +164,7 @@ func NewFlagSet() *pflag.FlagSet {
 	flagSet.Int("redis-connection-idle-timeout", 0, "Redis connection idle timeout seconds, if Redis timeout option is non-zero, the --redis-connection-idle-timeout must be less then Redis timeout option")
 	flagSet.String("signature-key", "", "GAP-Signature request signature key (algorithm:secretkey)")
 	flagSet.Bool("gcp-healthchecks", false, "Enable GCP/GKE healthcheck endpoints")
+	flagSet.Duration("shutdown-duration", 0, "Amount of time to continue serving traffic after receiving an exit signal with readiness endpoint set to false.")
 
 	flagSet.AddFlagSet(cookieFlagSet())
 	flagSet.AddFlagSet(loggingFlagSet())
diff --git a/pkg/http/server.go b/pkg/http/server.go
index fe76427a..25b1b0df 100644
--- a/pkg/http/server.go
+++ b/pkg/http/server.go
@@ -40,12 +40,16 @@ type Opts struct {
 
 	// Let testing infrastructure circumvent parsing file descriptors
 	fdFiles []*os.File
+
+	// Graceful shutdown duration
+	ShutdownDuration time.Duration
 }
 
 // NewServer creates a new Server from the options given.
 func NewServer(opts Opts) (Server, error) {
 	s := &server{
-		handler: opts.Handler,
+		handler:          opts.Handler,
+		shutdownDuration: opts.ShutdownDuration,
 	}
 
 	if len(opts.fdFiles) > 0 {
@@ -71,6 +75,9 @@ type server struct {
 
 	// ensure activation.Files are called once
 	fdFiles []*os.File
+
+	// Graceful shutdown duration
+	shutdownDuration time.Duration
 }
 
 // setupListener sets the server listener if the HTTP server is enabled.
@@ -214,10 +221,16 @@ func (s *server) startServer(ctx context.Context, listener net.Listener) error {
 
 	g.Go(func() error {
 		<-groupCtx.Done()
+		logger.Printf("Context canceled. Waiting %s before shutting down the listeners.", s.shutdownDuration)
+
+		time.Sleep(s.shutdownDuration)
+
+		logger.Printf("Shutting down listener.")
 
 		if err := srv.Shutdown(context.Background()); err != nil {
 			return fmt.Errorf("error shutting down server: %v", err)
 		}
+
 		return nil
 	})
 
diff --git a/pkg/middleware/readynesscheck.go b/pkg/middleware/readynesscheck.go
index aee871e1..6977cf2e 100644
--- a/pkg/middleware/readynesscheck.go
+++ b/pkg/middleware/readynesscheck.go
@@ -16,14 +16,19 @@ type Verifiable interface {
 
 // NewReadynessCheck returns a middleware that performs deep health checks
 // (verifies the connection to any underlying store) on a specific `path`
-func NewReadynessCheck(path string, verifiable Verifiable) alice.Constructor {
+func NewReadynessCheck(ctx context.Context, path string, verifiable Verifiable) alice.Constructor {
 	return func(next http.Handler) http.Handler {
-		return readynessCheck(path, verifiable, next)
+		return readynessCheck(ctx, path, verifiable, next)
 	}
 }
 
-func readynessCheck(path string, verifiable Verifiable, next http.Handler) http.Handler {
+func readynessCheck(ctx context.Context, path string, verifiable Verifiable, next http.Handler) http.Handler {
 	return http.HandlerFunc(func(rw http.ResponseWriter, req *http.Request) {
+		if ctx.Err() != nil {
+			rw.WriteHeader(http.StatusServiceUnavailable)
+			fmt.Fprintf(rw, "Shutting down")
+			return
+		}
 		if path != "" && req.URL.EscapedPath() == path {
 			if err := verifiable.VerifyConnection(req.Context()); err != nil {
 				rw.WriteHeader(http.StatusInternalServerError)
diff --git a/pkg/middleware/readynesscheck_test.go b/pkg/middleware/readynesscheck_test.go
index 618c27b8..952fc3f0 100644
--- a/pkg/middleware/readynesscheck_test.go
+++ b/pkg/middleware/readynesscheck_test.go
@@ -25,7 +25,9 @@ var _ = Describe("ReadynessCheck suite", func() {
 
 			rw := httptest.NewRecorder()
 
-			handler := NewReadynessCheck(in.readyPath, in.healthVerifiable)(http.NotFoundHandler())
+			ctx := context.Background()
+
+			handler := NewReadynessCheck(ctx, in.readyPath, in.healthVerifiable)(http.NotFoundHandler())
 			handler.ServeHTTP(rw, req)
 
 			Expect(rw.Code).To(Equal(in.expectedStatus))