TUN-528: Move cloudflared into a separate repo

vendor/golang.org/x/crypto/acme/autocert/cache.go

@@ -0,0 +1,130 @@
+// Copyright 2016 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+package autocert
+
+import (
+	"context"
+	"errors"
+	"io/ioutil"
+	"os"
+	"path/filepath"
+)
+
+// ErrCacheMiss is returned when a certificate is not found in cache.
+var ErrCacheMiss = errors.New("acme/autocert: certificate cache miss")
+
+// Cache is used by Manager to store and retrieve previously obtained certificates
+// and other account data as opaque blobs.
+//
+// Cache implementations should not rely on the key naming pattern. Keys can
+// include any printable ASCII characters, except the following: \/:*?"<>|
+type Cache interface {
+	// Get returns a certificate data for the specified key.
+	// If there's no such key, Get returns ErrCacheMiss.
+	Get(ctx context.Context, key string) ([]byte, error)
+
+	// Put stores the data in the cache under the specified key.
+	// Underlying implementations may use any data storage format,
+	// as long as the reverse operation, Get, results in the original data.
+	Put(ctx context.Context, key string, data []byte) error
+
+	// Delete removes a certificate data from the cache under the specified key.
+	// If there's no such key in the cache, Delete returns nil.
+	Delete(ctx context.Context, key string) error
+}
+
+// DirCache implements Cache using a directory on the local filesystem.
+// If the directory does not exist, it will be created with 0700 permissions.
+type DirCache string
+
+// Get reads a certificate data from the specified file name.
+func (d DirCache) Get(ctx context.Context, name string) ([]byte, error) {
+	name = filepath.Join(string(d), name)
+	var (
+		data []byte
+		err  error
+		done = make(chan struct{})
+	)
+	go func() {
+		data, err = ioutil.ReadFile(name)
+		close(done)
+	}()
+	select {
+	case <-ctx.Done():
+		return nil, ctx.Err()
+	case <-done:
+	}
+	if os.IsNotExist(err) {
+		return nil, ErrCacheMiss
+	}
+	return data, err
+}
+
+// Put writes the certificate data to the specified file name.
+// The file will be created with 0600 permissions.
+func (d DirCache) Put(ctx context.Context, name string, data []byte) error {
+	if err := os.MkdirAll(string(d), 0700); err != nil {
+		return err
+	}
+
+	done := make(chan struct{})
+	var err error
+	go func() {
+		defer close(done)
+		var tmp string
+		if tmp, err = d.writeTempFile(name, data); err != nil {
+			return
+		}
+		select {
+		case <-ctx.Done():
+			// Don't overwrite the file if the context was canceled.
+		default:
+			newName := filepath.Join(string(d), name)
+			err = os.Rename(tmp, newName)
+		}
+	}()
+	select {
+	case <-ctx.Done():
+		return ctx.Err()
+	case <-done:
+	}
+	return err
+}
+
+// Delete removes the specified file name.
+func (d DirCache) Delete(ctx context.Context, name string) error {
+	name = filepath.Join(string(d), name)
+	var (
+		err  error
+		done = make(chan struct{})
+	)
+	go func() {
+		err = os.Remove(name)
+		close(done)
+	}()
+	select {
+	case <-ctx.Done():
+		return ctx.Err()
+	case <-done:
+	}
+	if err != nil && !os.IsNotExist(err) {
+		return err
+	}
+	return nil
+}
+
+// writeTempFile writes b to a temporary file, closes the file and returns its path.
+func (d DirCache) writeTempFile(prefix string, b []byte) (string, error) {
+	// TempFile uses 0600 permissions
+	f, err := ioutil.TempFile(string(d), prefix)
+	if err != nil {
+		return "", err
+	}
+	if _, err := f.Write(b); err != nil {
+		f.Close()
+		return "", err
+	}
+	return f.Name(), f.Close()
+}

vendor/golang.org/x/crypto/acme/autocert/cache_test.go

@@ -0,0 +1,58 @@
+// Copyright 2016 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+package autocert
+
+import (
+	"context"
+	"io/ioutil"
+	"os"
+	"path/filepath"
+	"reflect"
+	"testing"
+)
+
+// make sure DirCache satisfies Cache interface
+var _ Cache = DirCache("/")
+
+func TestDirCache(t *testing.T) {
+	dir, err := ioutil.TempDir("", "autocert")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer os.RemoveAll(dir)
+	dir = filepath.Join(dir, "certs") // a nonexistent dir
+	cache := DirCache(dir)
+	ctx := context.Background()
+
+	// test cache miss
+	if _, err := cache.Get(ctx, "nonexistent"); err != ErrCacheMiss {
+		t.Errorf("get: %v; want ErrCacheMiss", err)
+	}
+
+	// test put/get
+	b1 := []byte{1}
+	if err := cache.Put(ctx, "dummy", b1); err != nil {
+		t.Fatalf("put: %v", err)
+	}
+	b2, err := cache.Get(ctx, "dummy")
+	if err != nil {
+		t.Fatalf("get: %v", err)
+	}
+	if !reflect.DeepEqual(b1, b2) {
+		t.Errorf("b1 = %v; want %v", b1, b2)
+	}
+	name := filepath.Join(dir, "dummy")
+	if _, err := os.Stat(name); err != nil {
+		t.Error(err)
+	}
+
+	// test delete
+	if err := cache.Delete(ctx, "dummy"); err != nil {
+		t.Fatalf("delete: %v", err)
+	}
+	if _, err := cache.Get(ctx, "dummy"); err != ErrCacheMiss {
+		t.Errorf("get: %v; want ErrCacheMiss", err)
+	}
+}

vendor/golang.org/x/crypto/acme/autocert/example_test.go

@@ -0,0 +1,36 @@
+// Copyright 2017 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+package autocert_test
+
+import (
+	"crypto/tls"
+	"fmt"
+	"log"
+	"net/http"
+
+	"golang.org/x/crypto/acme/autocert"
+)
+
+func ExampleNewListener() {
+	mux := http.NewServeMux()
+	mux.HandleFunc("/", func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintf(w, "Hello, TLS user! Your config: %+v", r.TLS)
+	})
+	log.Fatal(http.Serve(autocert.NewListener("example.com"), mux))
+}
+
+func ExampleManager() {
+	m := &autocert.Manager{
+		Cache:      autocert.DirCache("secret-dir"),
+		Prompt:     autocert.AcceptTOS,
+		HostPolicy: autocert.HostWhitelist("example.org"),
+	}
+	go http.ListenAndServe(":http", m.HTTPHandler(nil))
+	s := &http.Server{
+		Addr:      ":https",
+		TLSConfig: &tls.Config{GetCertificate: m.GetCertificate},
+	}
+	s.ListenAndServeTLS("", "")
+}

vendor/golang.org/x/crypto/acme/autocert/listener.go

@@ -0,0 +1,160 @@
+// Copyright 2017 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+package autocert
+
+import (
+	"crypto/tls"
+	"log"
+	"net"
+	"os"
+	"path/filepath"
+	"runtime"
+	"time"
+)
+
+// NewListener returns a net.Listener that listens on the standard TLS
+// port (443) on all interfaces and returns *tls.Conn connections with
+// LetsEncrypt certificates for the provided domain or domains.
+//
+// It enables one-line HTTPS servers:
+//
+//     log.Fatal(http.Serve(autocert.NewListener("example.com"), handler))
+//
+// NewListener is a convenience function for a common configuration.
+// More complex or custom configurations can use the autocert.Manager
+// type instead.
+//
+// Use of this function implies acceptance of the LetsEncrypt Terms of
+// Service. If domains is not empty, the provided domains are passed
+// to HostWhitelist. If domains is empty, the listener will do
+// LetsEncrypt challenges for any requested domain, which is not
+// recommended.
+//
+// Certificates are cached in a "golang-autocert" directory under an
+// operating system-specific cache or temp directory. This may not
+// be suitable for servers spanning multiple machines.
+//
+// The returned listener uses a *tls.Config that enables HTTP/2, and
+// should only be used with servers that support HTTP/2.
+//
+// The returned Listener also enables TCP keep-alives on the accepted
+// connections. The returned *tls.Conn are returned before their TLS
+// handshake has completed.
+func NewListener(domains ...string) net.Listener {
+	m := &Manager{
+		Prompt: AcceptTOS,
+	}
+	if len(domains) > 0 {
+		m.HostPolicy = HostWhitelist(domains...)
+	}
+	dir := cacheDir()
+	if err := os.MkdirAll(dir, 0700); err != nil {
+		log.Printf("warning: autocert.NewListener not using a cache: %v", err)
+	} else {
+		m.Cache = DirCache(dir)
+	}
+	return m.Listener()
+}
+
+// Listener listens on the standard TLS port (443) on all interfaces
+// and returns a net.Listener returning *tls.Conn connections.
+//
+// The returned listener uses a *tls.Config that enables HTTP/2, and
+// should only be used with servers that support HTTP/2.
+//
+// The returned Listener also enables TCP keep-alives on the accepted
+// connections. The returned *tls.Conn are returned before their TLS
+// handshake has completed.
+//
+// Unlike NewListener, it is the caller's responsibility to initialize
+// the Manager m's Prompt, Cache, HostPolicy, and other desired options.
+func (m *Manager) Listener() net.Listener {
+	ln := &listener{
+		m: m,
+		conf: &tls.Config{
+			GetCertificate: m.GetCertificate,           // bonus: panic on nil m
+			NextProtos:     []string{"h2", "http/1.1"}, // Enable HTTP/2
+		},
+	}
+	ln.tcpListener, ln.tcpListenErr = net.Listen("tcp", ":443")
+	return ln
+}
+
+type listener struct {
+	m    *Manager
+	conf *tls.Config
+
+	tcpListener  net.Listener
+	tcpListenErr error
+}
+
+func (ln *listener) Accept() (net.Conn, error) {
+	if ln.tcpListenErr != nil {
+		return nil, ln.tcpListenErr
+	}
+	conn, err := ln.tcpListener.Accept()
+	if err != nil {
+		return nil, err
+	}
+	tcpConn := conn.(*net.TCPConn)
+
+	// Because Listener is a convenience function, help out with
+	// this too.  This is not possible for the caller to set once
+	// we return a *tcp.Conn wrapping an inaccessible net.Conn.
+	// If callers don't want this, they can do things the manual
+	// way and tweak as needed. But this is what net/http does
+	// itself, so copy that. If net/http changes, we can change
+	// here too.
+	tcpConn.SetKeepAlive(true)
+	tcpConn.SetKeepAlivePeriod(3 * time.Minute)
+
+	return tls.Server(tcpConn, ln.conf), nil
+}
+
+func (ln *listener) Addr() net.Addr {
+	if ln.tcpListener != nil {
+		return ln.tcpListener.Addr()
+	}
+	// net.Listen failed. Return something non-nil in case callers
+	// call Addr before Accept:
+	return &net.TCPAddr{IP: net.IP{0, 0, 0, 0}, Port: 443}
+}
+
+func (ln *listener) Close() error {
+	if ln.tcpListenErr != nil {
+		return ln.tcpListenErr
+	}
+	return ln.tcpListener.Close()
+}
+
+func homeDir() string {
+	if runtime.GOOS == "windows" {
+		return os.Getenv("HOMEDRIVE") + os.Getenv("HOMEPATH")
+	}
+	if h := os.Getenv("HOME"); h != "" {
+		return h
+	}
+	return "/"
+}
+
+func cacheDir() string {
+	const base = "golang-autocert"
+	switch runtime.GOOS {
+	case "darwin":
+		return filepath.Join(homeDir(), "Library", "Caches", base)
+	case "windows":
+		for _, ev := range []string{"APPDATA", "CSIDL_APPDATA", "TEMP", "TMP"} {
+			if v := os.Getenv(ev); v != "" {
+				return filepath.Join(v, base)
+			}
+		}
+		// Worst case:
+		return filepath.Join(homeDir(), base)
+	}
+	if xdg := os.Getenv("XDG_CACHE_HOME"); xdg != "" {
+		return filepath.Join(xdg, base)
+	}
+	return filepath.Join(homeDir(), ".cache", base)
+}

vendor/golang.org/x/crypto/acme/autocert/renewal.go

@@ -0,0 +1,141 @@
+// Copyright 2016 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+package autocert
+
+import (
+	"context"
+	"crypto"
+	"sync"
+	"time"
+)
+
+// renewJitter is the maximum deviation from Manager.RenewBefore.
+const renewJitter = time.Hour
+
+// domainRenewal tracks the state used by the periodic timers
+// renewing a single domain's cert.
+type domainRenewal struct {
+	m   *Manager
+	ck  certKey
+	key crypto.Signer
+
+	timerMu sync.Mutex
+	timer   *time.Timer
+}
+
+// start starts a cert renewal timer at the time
+// defined by the certificate expiration time exp.
+//
+// If the timer is already started, calling start is a noop.
+func (dr *domainRenewal) start(exp time.Time) {
+	dr.timerMu.Lock()
+	defer dr.timerMu.Unlock()
+	if dr.timer != nil {
+		return
+	}
+	dr.timer = time.AfterFunc(dr.next(exp), dr.renew)
+}
+
+// stop stops the cert renewal timer.
+// If the timer is already stopped, calling stop is a noop.
+func (dr *domainRenewal) stop() {
+	dr.timerMu.Lock()
+	defer dr.timerMu.Unlock()
+	if dr.timer == nil {
+		return
+	}
+	dr.timer.Stop()
+	dr.timer = nil
+}
+
+// renew is called periodically by a timer.
+// The first renew call is kicked off by dr.start.
+func (dr *domainRenewal) renew() {
+	dr.timerMu.Lock()
+	defer dr.timerMu.Unlock()
+	if dr.timer == nil {
+		return
+	}
+
+	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Minute)
+	defer cancel()
+	// TODO: rotate dr.key at some point?
+	next, err := dr.do(ctx)
+	if err != nil {
+		next = renewJitter / 2
+		next += time.Duration(pseudoRand.int63n(int64(next)))
+	}
+	dr.timer = time.AfterFunc(next, dr.renew)
+	testDidRenewLoop(next, err)
+}
+
+// updateState locks and replaces the relevant Manager.state item with the given
+// state. It additionally updates dr.key with the given state's key.
+func (dr *domainRenewal) updateState(state *certState) {
+	dr.m.stateMu.Lock()
+	defer dr.m.stateMu.Unlock()
+	dr.key = state.key
+	dr.m.state[dr.ck] = state
+}
+
+// do is similar to Manager.createCert but it doesn't lock a Manager.state item.
+// Instead, it requests a new certificate independently and, upon success,
+// replaces dr.m.state item with a new one and updates cache for the given domain.
+//
+// It may lock and update the Manager.state if the expiration date of the currently
+// cached cert is far enough in the future.
+//
+// The returned value is a time interval after which the renewal should occur again.
+func (dr *domainRenewal) do(ctx context.Context) (time.Duration, error) {
+	// a race is likely unavoidable in a distributed environment
+	// but we try nonetheless
+	if tlscert, err := dr.m.cacheGet(ctx, dr.ck); err == nil {
+		next := dr.next(tlscert.Leaf.NotAfter)
+		if next > dr.m.renewBefore()+renewJitter {
+			signer, ok := tlscert.PrivateKey.(crypto.Signer)
+			if ok {
+				state := &certState{
+					key:  signer,
+					cert: tlscert.Certificate,
+					leaf: tlscert.Leaf,
+				}
+				dr.updateState(state)
+				return next, nil
+			}
+		}
+	}
+
+	der, leaf, err := dr.m.authorizedCert(ctx, dr.key, dr.ck)
+	if err != nil {
+		return 0, err
+	}
+	state := &certState{
+		key:  dr.key,
+		cert: der,
+		leaf: leaf,
+	}
+	tlscert, err := state.tlscert()
+	if err != nil {
+		return 0, err
+	}
+	if err := dr.m.cachePut(ctx, dr.ck, tlscert); err != nil {
+		return 0, err
+	}
+	dr.updateState(state)
+	return dr.next(leaf.NotAfter), nil
+}
+
+func (dr *domainRenewal) next(expiry time.Time) time.Duration {
+	d := expiry.Sub(timeNow()) - dr.m.renewBefore()
+	// add a bit of randomness to renew deadline
+	n := pseudoRand.int63n(int64(renewJitter))
+	d -= time.Duration(n)
+	if d < 0 {
+		return 0
+	}
+	return d
+}
+
+var testDidRenewLoop = func(next time.Duration, err error) {}

vendor/golang.org/x/crypto/acme/autocert/renewal_test.go

@@ -0,0 +1,329 @@
+// Copyright 2016 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+package autocert
+
+import (
+	"context"
+	"crypto/ecdsa"
+	"crypto/elliptic"
+	"crypto/rand"
+	"crypto/tls"
+	"crypto/x509"
+	"encoding/base64"
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+	"time"
+
+	"golang.org/x/crypto/acme"
+)
+
+func TestRenewalNext(t *testing.T) {
+	now := time.Now()
+	timeNow = func() time.Time { return now }
+	defer func() { timeNow = time.Now }()
+
+	man := &Manager{RenewBefore: 7 * 24 * time.Hour}
+	defer man.stopRenew()
+	tt := []struct {
+		expiry   time.Time
+		min, max time.Duration
+	}{
+		{now.Add(90 * 24 * time.Hour), 83*24*time.Hour - renewJitter, 83 * 24 * time.Hour},
+		{now.Add(time.Hour), 0, 1},
+		{now, 0, 1},
+		{now.Add(-time.Hour), 0, 1},
+	}
+
+	dr := &domainRenewal{m: man}
+	for i, test := range tt {
+		next := dr.next(test.expiry)
+		if next < test.min || test.max < next {
+			t.Errorf("%d: next = %v; want between %v and %v", i, next, test.min, test.max)
+		}
+	}
+}
+
+func TestRenewFromCache(t *testing.T) {
+	// ACME CA server stub
+	var ca *httptest.Server
+	ca = httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Replay-Nonce", "nonce")
+		if r.Method == "HEAD" {
+			// a nonce request
+			return
+		}
+
+		switch r.URL.Path {
+		// discovery
+		case "/":
+			if err := discoTmpl.Execute(w, ca.URL); err != nil {
+				t.Fatalf("discoTmpl: %v", err)
+			}
+		// client key registration
+		case "/new-reg":
+			w.Write([]byte("{}"))
+		// domain authorization
+		case "/new-authz":
+			w.Header().Set("Location", ca.URL+"/authz/1")
+			w.WriteHeader(http.StatusCreated)
+			w.Write([]byte(`{"status": "valid"}`))
+		// cert request
+		case "/new-cert":
+			var req struct {
+				CSR string `json:"csr"`
+			}
+			decodePayload(&req, r.Body)
+			b, _ := base64.RawURLEncoding.DecodeString(req.CSR)
+			csr, err := x509.ParseCertificateRequest(b)
+			if err != nil {
+				t.Fatalf("new-cert: CSR: %v", err)
+			}
+			der, err := dummyCert(csr.PublicKey, exampleDomain)
+			if err != nil {
+				t.Fatalf("new-cert: dummyCert: %v", err)
+			}
+			chainUp := fmt.Sprintf("<%s/ca-cert>; rel=up", ca.URL)
+			w.Header().Set("Link", chainUp)
+			w.WriteHeader(http.StatusCreated)
+			w.Write(der)
+		// CA chain cert
+		case "/ca-cert":
+			der, err := dummyCert(nil, "ca")
+			if err != nil {
+				t.Fatalf("ca-cert: dummyCert: %v", err)
+			}
+			w.Write(der)
+		default:
+			t.Errorf("unrecognized r.URL.Path: %s", r.URL.Path)
+		}
+	}))
+	defer ca.Close()
+
+	man := &Manager{
+		Prompt:      AcceptTOS,
+		Cache:       newMemCache(t),
+		RenewBefore: 24 * time.Hour,
+		Client: &acme.Client{
+			DirectoryURL: ca.URL,
+		},
+	}
+	defer man.stopRenew()
+
+	// cache an almost expired cert
+	key, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+	if err != nil {
+		t.Fatal(err)
+	}
+	now := time.Now()
+	cert, err := dateDummyCert(key.Public(), now.Add(-2*time.Hour), now.Add(time.Minute), exampleDomain)
+	if err != nil {
+		t.Fatal(err)
+	}
+	tlscert := &tls.Certificate{PrivateKey: key, Certificate: [][]byte{cert}}
+	if err := man.cachePut(context.Background(), exampleCertKey, tlscert); err != nil {
+		t.Fatal(err)
+	}
+
+	// veriy the renewal happened
+	defer func() {
+		testDidRenewLoop = func(next time.Duration, err error) {}
+	}()
+	done := make(chan struct{})
+	testDidRenewLoop = func(next time.Duration, err error) {
+		defer close(done)
+		if err != nil {
+			t.Errorf("testDidRenewLoop: %v", err)
+		}
+		// Next should be about 90 days:
+		// dummyCert creates 90days expiry + account for man.RenewBefore.
+		// Previous expiration was within 1 min.
+		future := 88 * 24 * time.Hour
+		if next < future {
+			t.Errorf("testDidRenewLoop: next = %v; want >= %v", next, future)
+		}
+
+		// ensure the new cert is cached
+		after := time.Now().Add(future)
+		tlscert, err := man.cacheGet(context.Background(), exampleCertKey)
+		if err != nil {
+			t.Fatalf("man.cacheGet: %v", err)
+		}
+		if !tlscert.Leaf.NotAfter.After(after) {
+			t.Errorf("cache leaf.NotAfter = %v; want > %v", tlscert.Leaf.NotAfter, after)
+		}
+
+		// verify the old cert is also replaced in memory
+		man.stateMu.Lock()
+		defer man.stateMu.Unlock()
+		s := man.state[exampleCertKey]
+		if s == nil {
+			t.Fatalf("m.state[%q] is nil", exampleCertKey)
+		}
+		tlscert, err = s.tlscert()
+		if err != nil {
+			t.Fatalf("s.tlscert: %v", err)
+		}
+		if !tlscert.Leaf.NotAfter.After(after) {
+			t.Errorf("state leaf.NotAfter = %v; want > %v", tlscert.Leaf.NotAfter, after)
+		}
+	}
+
+	// trigger renew
+	hello := clientHelloInfo(exampleDomain, true)
+	if _, err := man.GetCertificate(hello); err != nil {
+		t.Fatal(err)
+	}
+
+	// wait for renew loop
+	select {
+	case <-time.After(10 * time.Second):
+		t.Fatal("renew took too long to occur")
+	case <-done:
+	}
+}
+
+func TestRenewFromCacheAlreadyRenewed(t *testing.T) {
+	man := &Manager{
+		Prompt:      AcceptTOS,
+		Cache:       newMemCache(t),
+		RenewBefore: 24 * time.Hour,
+		Client: &acme.Client{
+			DirectoryURL: "invalid",
+		},
+	}
+	defer man.stopRenew()
+
+	// cache a recently renewed cert with a different private key
+	newKey, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+	if err != nil {
+		t.Fatal(err)
+	}
+	now := time.Now()
+	newCert, err := dateDummyCert(newKey.Public(), now.Add(-2*time.Hour), now.Add(time.Hour*24*90), exampleDomain)
+	if err != nil {
+		t.Fatal(err)
+	}
+	newLeaf, err := validCert(exampleCertKey, [][]byte{newCert}, newKey)
+	if err != nil {
+		t.Fatal(err)
+	}
+	newTLSCert := &tls.Certificate{PrivateKey: newKey, Certificate: [][]byte{newCert}, Leaf: newLeaf}
+	if err := man.cachePut(context.Background(), exampleCertKey, newTLSCert); err != nil {
+		t.Fatal(err)
+	}
+
+	// set internal state to an almost expired cert
+	key, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+	if err != nil {
+		t.Fatal(err)
+	}
+	oldCert, err := dateDummyCert(key.Public(), now.Add(-2*time.Hour), now.Add(time.Minute), exampleDomain)
+	if err != nil {
+		t.Fatal(err)
+	}
+	oldLeaf, err := validCert(exampleCertKey, [][]byte{oldCert}, key)
+	if err != nil {
+		t.Fatal(err)
+	}
+	man.stateMu.Lock()
+	if man.state == nil {
+		man.state = make(map[certKey]*certState)
+	}
+	s := &certState{
+		key:  key,
+		cert: [][]byte{oldCert},
+		leaf: oldLeaf,
+	}
+	man.state[exampleCertKey] = s
+	man.stateMu.Unlock()
+
+	// veriy the renewal accepted the newer cached cert
+	defer func() {
+		testDidRenewLoop = func(next time.Duration, err error) {}
+	}()
+	done := make(chan struct{})
+	testDidRenewLoop = func(next time.Duration, err error) {
+		defer close(done)
+		if err != nil {
+			t.Errorf("testDidRenewLoop: %v", err)
+		}
+		// Next should be about 90 days
+		// Previous expiration was within 1 min.
+		future := 88 * 24 * time.Hour
+		if next < future {
+			t.Errorf("testDidRenewLoop: next = %v; want >= %v", next, future)
+		}
+
+		// ensure the cached cert was not modified
+		tlscert, err := man.cacheGet(context.Background(), exampleCertKey)
+		if err != nil {
+			t.Fatalf("man.cacheGet: %v", err)
+		}
+		if !tlscert.Leaf.NotAfter.Equal(newLeaf.NotAfter) {
+			t.Errorf("cache leaf.NotAfter = %v; want == %v", tlscert.Leaf.NotAfter, newLeaf.NotAfter)
+		}
+
+		// verify the old cert is also replaced in memory
+		man.stateMu.Lock()
+		defer man.stateMu.Unlock()
+		s := man.state[exampleCertKey]
+		if s == nil {
+			t.Fatalf("m.state[%q] is nil", exampleCertKey)
+		}
+		stateKey := s.key.Public().(*ecdsa.PublicKey)
+		if stateKey.X.Cmp(newKey.X) != 0 || stateKey.Y.Cmp(newKey.Y) != 0 {
+			t.Fatalf("state key was not updated from cache x: %v y: %v; want x: %v y: %v", stateKey.X, stateKey.Y, newKey.X, newKey.Y)
+		}
+		tlscert, err = s.tlscert()
+		if err != nil {
+			t.Fatalf("s.tlscert: %v", err)
+		}
+		if !tlscert.Leaf.NotAfter.Equal(newLeaf.NotAfter) {
+			t.Errorf("state leaf.NotAfter = %v; want == %v", tlscert.Leaf.NotAfter, newLeaf.NotAfter)
+		}
+
+		// verify the private key is replaced in the renewal state
+		r := man.renewal[exampleCertKey]
+		if r == nil {
+			t.Fatalf("m.renewal[%q] is nil", exampleCertKey)
+		}
+		renewalKey := r.key.Public().(*ecdsa.PublicKey)
+		if renewalKey.X.Cmp(newKey.X) != 0 || renewalKey.Y.Cmp(newKey.Y) != 0 {
+			t.Fatalf("renewal private key was not updated from cache x: %v y: %v; want x: %v y: %v", renewalKey.X, renewalKey.Y, newKey.X, newKey.Y)
+		}
+
+	}
+
+	// assert the expiring cert is returned from state
+	hello := clientHelloInfo(exampleDomain, true)
+	tlscert, err := man.GetCertificate(hello)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !oldLeaf.NotAfter.Equal(tlscert.Leaf.NotAfter) {
+		t.Errorf("state leaf.NotAfter = %v; want == %v", tlscert.Leaf.NotAfter, oldLeaf.NotAfter)
+	}
+
+	// trigger renew
+	go man.renew(exampleCertKey, s.key, s.leaf.NotAfter)
+
+	// wait for renew loop
+	select {
+	case <-time.After(10 * time.Second):
+		t.Fatal("renew took too long to occur")
+	case <-done:
+		// assert the new cert is returned from state after renew
+		hello := clientHelloInfo(exampleDomain, true)
+		tlscert, err := man.GetCertificate(hello)
+		if err != nil {
+			t.Fatal(err)
+		}
+		if !newTLSCert.Leaf.NotAfter.Equal(tlscert.Leaf.NotAfter) {
+			t.Errorf("state leaf.NotAfter = %v; want == %v", tlscert.Leaf.NotAfter, newTLSCert.Leaf.NotAfter)
+		}
+	}
+}