diff --git a/integration/hsm/helpers.go b/integration/hsm/helpers.go
index bf2589a98c8cc..d531c7e090bc2 100644
--- a/integration/hsm/helpers.go
+++ b/integration/hsm/helpers.go
@@ -26,6 +26,7 @@ import (
 	"time"
 
 	"github.com/gravitational/trace"
+	"github.com/jonboulle/clockwork"
 	"github.com/stretchr/testify/require"
 
 	"github.com/gravitational/teleport/api/types"
@@ -60,9 +61,6 @@ func newTeleportService(t *testing.T, config *servicecfg.Config, name string) *t
 		serviceChannel: make(chan *service.TeleportProcess, 1),
 		errorChannel:   make(chan error, 1),
 	}
-	t.Cleanup(func() {
-		require.NoError(t, s.close(), "error while closing %s during test cleanup", name)
-	})
 	return s
 }
 
@@ -111,17 +109,43 @@ func (t *teleportService) waitForNewProcess(ctx context.Context) error {
 	return nil
 }
 
+func (t *teleportService) waitForEvent(ctx context.Context, event string) error {
+	ctx, cancel := context.WithCancel(ctx)
+	defer cancel()
+	waitForEventErr := make(chan error)
+	go func() {
+		_, err := t.process.WaitForEvent(ctx, event)
+		select {
+		case waitForEventErr <- err:
+		case <-ctx.Done():
+		}
+	}()
+	select {
+	case err := <-waitForEventErr:
+		return trace.Wrap(err)
+	case err := <-t.errorChannel:
+		if err != nil {
+			return trace.Wrap(err, "process unexpectedly exited while waiting for event %s", event)
+		}
+		return trace.Errorf("process unexpectedly exited while waiting for event %s", event)
+	case <-t.serviceChannel:
+		return trace.Errorf("process unexpectedly reloaded while waiting for event %s", event)
+	case <-ctx.Done():
+		return trace.Wrap(ctx.Err())
+	}
+}
+
 func (t *teleportService) waitForReady(ctx context.Context) error {
 	t.log.Debugf("%s gen %d: waiting for TeleportReadyEvent", t.name, t.processGeneration)
-	if _, err := t.process.WaitForEvent(ctx, service.TeleportReadyEvent); err != nil {
-		return trace.Wrap(err, "timed out waiting for %s gen %d to be ready", t.name, t.processGeneration)
+	if err := t.waitForEvent(ctx, service.TeleportReadyEvent); err != nil {
+		return trace.Wrap(err, "waiting for %s gen %d to be ready", t.name, t.processGeneration)
 	}
 	t.log.Debugf("%s gen %d: got TeleportReadyEvent", t.name, t.processGeneration)
 	// If this is an Auth server, also wait for AuthIdentityEvent so that we
 	// can safely read the admin credentials and create a test client.
 	if t.process.GetAuthServer() != nil {
 		t.log.Debugf("%s gen %d: waiting for AuthIdentityEvent", t.name, t.processGeneration)
-		if _, err := t.process.WaitForEvent(ctx, service.AuthIdentityEvent); err != nil {
+		if err := t.waitForEvent(ctx, service.AuthIdentityEvent); err != nil {
 			return trace.Wrap(err, "%s gen %d: timed out waiting AuthIdentityEvent", t.name, t.processGeneration)
 		}
 		t.log.Debugf("%s gen %d: got AuthIdentityEvent", t.name, t.processGeneration)
@@ -170,7 +194,7 @@ func (t *teleportService) waitForLocalAdditionalKeys(ctx context.Context) error
 		if err != nil {
 			return trace.Wrap(err)
 		}
-		if usableKeysResult.CAHasUsableKeys {
+		if usableKeysResult.CAHasPreferredKeyType {
 			break
 		}
 	}
@@ -180,7 +204,7 @@ func (t *teleportService) waitForLocalAdditionalKeys(ctx context.Context) error
 
 func (t *teleportService) waitForPhaseChange(ctx context.Context) error {
 	t.log.Debugf("%s gen %d: waiting for phase change", t.name, t.processGeneration)
-	if _, err := t.process.WaitForEvent(ctx, service.TeleportPhaseChangeEvent); err != nil {
+	if err := t.waitForEvent(ctx, service.TeleportPhaseChangeEvent); err != nil {
 		return trace.Wrap(err, "%s gen %d: timed out waiting for phase change", t.name, t.processGeneration)
 	}
 	t.log.Debugf("%s gen %d: changed phase", t.name, t.processGeneration)
@@ -237,6 +261,7 @@ func newAuthConfig(t *testing.T, log utils.Logger) *servicecfg.Config {
 	config.InstanceMetadataClient = cloud.NewDisabledIMDSClient()
 	config.MaxRetryPeriod = 25 * time.Millisecond
 	config.PollingPeriod = 2 * time.Second
+	config.Clock = fastClock(t)
 
 	config.Auth.Enabled = true
 	config.Auth.NoAudit = true
@@ -268,6 +293,7 @@ func newAuthConfig(t *testing.T, log utils.Logger) *servicecfg.Config {
 
 func newProxyConfig(t *testing.T, authAddr utils.NetAddr, log utils.Logger) *servicecfg.Config {
 	config := servicecfg.MakeDefaultConfig()
+	config.Version = defaults.TeleportConfigVersionV3
 	config.DataDir = t.TempDir()
 	config.CachePolicy.Enabled = true
 	config.Auth.Enabled = false
@@ -278,6 +304,7 @@ func newProxyConfig(t *testing.T, authAddr utils.NetAddr, log utils.Logger) *ser
 	config.InstanceMetadataClient = cloud.NewDisabledIMDSClient()
 	config.MaxRetryPeriod = 25 * time.Millisecond
 	config.PollingPeriod = 2 * time.Second
+	config.Clock = fastClock(t)
 
 	config.Proxy.Enabled = true
 	config.Proxy.DisableWebInterface = true
@@ -288,3 +315,24 @@ func newProxyConfig(t *testing.T, authAddr utils.NetAddr, log utils.Logger) *ser
 
 	return config
 }
+
+// fastClock returns a clock that runs at ~20x realtime.
+func fastClock(t *testing.T) clockwork.FakeClock {
+	// Start in the past to avoid cert not yet valid errors
+	clock := clockwork.NewFakeClockAt(time.Now().Add(-12 * time.Hour))
+	done := make(chan struct{})
+	t.Cleanup(func() { close(done) })
+	go func() {
+		for {
+			select {
+			case <-done:
+				return
+			default:
+			}
+			clock.BlockUntil(1)
+			clock.Advance(time.Second)
+			time.Sleep(50 * time.Millisecond)
+		}
+	}()
+	return clock
+}
diff --git a/integration/hsm/hsm_test.go b/integration/hsm/hsm_test.go
index c5ce0045272d0..c198a60a60e13 100644
--- a/integration/hsm/hsm_test.go
+++ b/integration/hsm/hsm_test.go
@@ -112,12 +112,6 @@ func liteBackendConfig(t *testing.T) *backend.Config {
 	}
 }
 
-func requireHSMAvailable(t *testing.T) {
-	if os.Getenv("SOFTHSM2_PATH") == "" && os.Getenv("TEST_GCP_KMS_KEYRING") == "" {
-		t.Skip("Skipping test because neither SOFTHSM2_PATH or TEST_GCP_KMS_KEYRING are set")
-	}
-}
-
 func requireETCDAvailable(t *testing.T) {
 	if os.Getenv("TELEPORT_ETCD_TEST") == "" {
 		t.Skip("Skipping test because TELEPORT_ETCD_TEST is not set")
@@ -126,8 +120,6 @@ func requireETCDAvailable(t *testing.T) {
 
 // Tests a single CA rotation with a single HSM auth server
 func TestHSMRotation(t *testing.T) {
-	requireHSMAvailable(t)
-
 	ctx, cancel := context.WithCancel(context.Background())
 	t.Cleanup(cancel)
 	log := utils.NewLoggerForTests()
@@ -229,11 +221,6 @@ func testAdminClient(t *testing.T, authDataDir string, authAddr string) {
 
 // Tests multiple CA rotations and rollbacks with 2 HSM auth servers in an HA configuration
 func TestHSMDualAuthRotation(t *testing.T) {
-	// TODO(nklaassen): fix this test and re-enable it.
-	// https://github.com/gravitational/teleport/issues/20217
-	t.Skip("TestHSMDualAuthRotation is temporarily disabled due to flakiness")
-
-	requireHSMAvailable(t)
 	requireETCDAvailable(t)
 
 	ctx, cancel := context.WithCancel(context.Background())
@@ -241,7 +228,7 @@ func TestHSMDualAuthRotation(t *testing.T) {
 	log := utils.NewLoggerForTests()
 	storageConfig := etcdBackendConfig(t)
 
-	// start a cluster with 1 auth server and a proxy
+	// start a cluster with 1 auth server
 	log.Debug("TestHSMDualAuthRotation: Starting auth server 1")
 	auth1Config := newHSMAuthConfig(t, storageConfig, log)
 	auth1 := newTeleportService(t, auth1Config, "auth1")
@@ -250,7 +237,6 @@ func TestHSMDualAuthRotation(t *testing.T) {
 			"failed to delete hsm keys during test cleanup")
 	})
 	authServices := teleportServices{auth1}
-	allServices := append(teleportServices{}, authServices...)
 	require.NoError(t, authServices.start(ctx), "auth service failed initial startup")
 
 	log.Debug("TestHSMDualAuthRotation: Starting load balancer")
@@ -264,23 +250,16 @@ func TestHSMDualAuthRotation(t *testing.T) {
 	go lb.Serve()
 	t.Cleanup(func() { require.NoError(t, lb.Close()) })
 
-	// start a proxy to make sure it can get creds at each stage of rotation
-	log.Debug("TestHSMDualAuthRotation: Starting proxy")
-	proxyConfig := newProxyConfig(t, utils.FromAddr(lb.Addr()), log)
-	proxy := newTeleportService(t, proxyConfig, "proxy")
-	require.NoError(t, proxy.start(ctx), "proxy failed initial startup")
-	allServices = append(allServices, proxy)
-
 	// add a new auth server
 	log.Debug("TestHSMDualAuthRotation: Starting auth server 2")
 	auth2Config := newHSMAuthConfig(t, storageConfig, log)
 	auth2 := newTeleportService(t, auth2Config, "auth2")
-	require.NoError(t, auth2.start(ctx))
+	err = auth2.start(ctx)
+	require.NoError(t, err, trace.DebugReport(err))
 	t.Cleanup(func() {
 		require.NoError(t, auth2.process.GetAuthServer().GetKeyStore().DeleteUnusedKeys(ctx, nil))
 	})
 	authServices = append(authServices, auth2)
-	allServices = append(allServices, auth2)
 
 	testAuth2Client := func(t *testing.T) {
 		testAdminClient(t, auth2Config.DataDir, auth2.authAddrString(t))
@@ -294,7 +273,7 @@ func TestHSMDualAuthRotation(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseInit,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForPhaseChange(ctx))
+				require.NoError(t, authServices.waitForPhaseChange(ctx))
 				require.NoError(t, authServices.waitForLocalAdditionalKeys(ctx))
 				testAuth2Client(t)
 			},
@@ -302,21 +281,21 @@ func TestHSMDualAuthRotation(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseUpdateClients,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testAuth2Client(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseUpdateServers,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testAuth2Client(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseStandby,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testAuth2Client(t)
 			},
 		},
@@ -360,7 +339,7 @@ func TestHSMDualAuthRotation(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseInit,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForPhaseChange(ctx))
+				require.NoError(t, authServices.waitForPhaseChange(ctx))
 				require.NoError(t, authServices.waitForLocalAdditionalKeys(ctx))
 				testLoadBalancedClient(t)
 			},
@@ -368,21 +347,21 @@ func TestHSMDualAuthRotation(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseRollback,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseStandby,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseInit,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForPhaseChange(ctx))
+				require.NoError(t, authServices.waitForPhaseChange(ctx))
 				require.NoError(t, authServices.waitForLocalAdditionalKeys(ctx))
 				testLoadBalancedClient(t)
 			},
@@ -390,28 +369,28 @@ func TestHSMDualAuthRotation(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseUpdateClients,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseRollback,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseStandby,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseInit,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForPhaseChange(ctx))
+				require.NoError(t, authServices.waitForPhaseChange(ctx))
 				require.NoError(t, authServices.waitForLocalAdditionalKeys(ctx))
 				testLoadBalancedClient(t)
 			},
@@ -419,28 +398,28 @@ func TestHSMDualAuthRotation(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseUpdateClients,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseUpdateServers,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseRollback,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseStandby,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				require.NoError(t, authServices.waitForRestart(ctx))
 				testLoadBalancedClient(t)
 			},
 		},
@@ -458,7 +437,6 @@ func TestHSMDualAuthRotation(t *testing.T) {
 
 // Tests a dual-auth server migration from raw keys to HSM keys
 func TestHSMMigrate(t *testing.T) {
-	requireHSMAvailable(t)
 	requireETCDAvailable(t)
 
 	ctx, cancel := context.WithCancel(context.Background())
@@ -494,12 +472,6 @@ func TestHSMMigrate(t *testing.T) {
 	go lb.Serve()
 	t.Cleanup(func() { require.NoError(t, lb.Close()) })
 
-	// start a proxy to make sure it can get creds at each stage of migration
-	log.Debug("TestHSMMigrate: Starting proxy")
-	proxyConfig := newProxyConfig(t, utils.FromAddr(lb.Addr()), log)
-	proxy := newTeleportService(t, proxyConfig, "proxy")
-	require.NoError(t, proxy.start(ctx))
-
 	testClient := func(t *testing.T) {
 		testAdminClient(t, auth1Config.DataDir, lb.Addr().String())
 	}
@@ -525,7 +497,6 @@ func TestHSMMigrate(t *testing.T) {
 	assert.Contains(t, alert.Spec.Message, "host")
 
 	authServices := teleportServices{auth1, auth2}
-	allServices := teleportServices{auth1, auth2, proxy}
 
 	stages := []struct {
 		targetPhase string
@@ -534,7 +505,7 @@ func TestHSMMigrate(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseInit,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForPhaseChange(ctx))
+				require.NoError(t, authServices.waitForPhaseChange(ctx))
 				require.NoError(t, authServices.waitForLocalAdditionalKeys(ctx))
 				testClient(t)
 			},
@@ -542,21 +513,24 @@ func TestHSMMigrate(t *testing.T) {
 		{
 			targetPhase: types.RotationPhaseUpdateClients,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				err := authServices.waitForRestart(ctx)
+				require.NoError(t, err, trace.DebugReport(err))
 				testClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseUpdateServers,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				err := authServices.waitForRestart(ctx)
+				require.NoError(t, err, trace.DebugReport(err))
 				testClient(t)
 			},
 		},
 		{
 			targetPhase: types.RotationPhaseStandby,
 			verify: func(t *testing.T) {
-				require.NoError(t, allServices.waitForRestart(ctx))
+				err := authServices.waitForRestart(ctx)
+				require.NoError(t, err, trace.DebugReport(err))
 				testClient(t)
 			},
 		},
@@ -586,9 +560,7 @@ func TestHSMMigrate(t *testing.T) {
 	auth2Config.Auth.KeyStore = keystore.HSMTestConfig(t)
 	auth2 = newTeleportService(t, auth2Config, "auth2")
 	require.NoError(t, auth2.start(ctx))
-
 	authServices = teleportServices{auth1, auth2}
-	allServices = teleportServices{auth1, auth2, proxy}
 
 	testClient(t)
 
@@ -614,8 +586,6 @@ func TestHSMMigrate(t *testing.T) {
 // TestHSMRevert tests a single-auth server migration from HSM keys back to
 // software keys.
 func TestHSMRevert(t *testing.T) {
-	requireHSMAvailable(t)
-
 	clock := clockwork.NewFakeClock()
 	ctx, cancel := context.WithCancel(context.Background())
 	t.Cleanup(cancel)
diff --git a/lib/auth/init.go b/lib/auth/init.go
index 5e74cc6e0c870..ae6b8b496b6c5 100644
--- a/lib/auth/init.go
+++ b/lib/auth/init.go
@@ -611,13 +611,22 @@ func initializeAuthority(ctx context.Context, asrv *Server, caID types.CertAuthI
 			if err := asrv.ensureLocalAdditionalKeys(ctx, ca); err != nil {
 				return nil, nil, trace.Wrap(err)
 			}
+			ca, err = asrv.Services.GetCertAuthority(ctx, caID, true)
+			if err != nil {
+				return nil, nil, trace.Wrap(err)
+			}
+			usableKeysResult, err = asrv.keyStore.HasUsableActiveKeys(ctx, ca)
+			if err != nil {
+				return nil, nil, trace.Wrap(err)
+			}
+		} else {
+			log.Warnf("This Auth Service is configured to use %s but the %s CA contains only %s. "+
+				"No new certificates can be signed with the existing keys. "+
+				"You must perform a CA rotation to generate new keys, or adjust your configuration to use the existing keys.",
+				usableKeysResult.PreferredKeyType,
+				caID.Type,
+				strings.Join(usableKeysResult.CAKeyTypes, " and "))
 		}
-		log.Warnf("This Auth Service is configured to use %s but the %s CA contains only %s. "+
-			"No new certificates can be signed with the existing keys. "+
-			"You must perform a CA rotation to generate new keys, or adjust your configuration to use the existing keys.",
-			usableKeysResult.PreferredKeyType,
-			caID.Type,
-			strings.Join(usableKeysResult.CAKeyTypes, " and "))
 	} else if !usableKeysResult.CAHasPreferredKeyType {
 		log.Warnf("This Auth Service is configured to use %s but the %s CA contains only %s. "+
 			"New certificates will continue to be signed with raw software keys but you must perform a CA rotation to begin using %s.",
diff --git a/lib/auth/keystore/pkcs11.go b/lib/auth/keystore/pkcs11.go
index d845a00265094..bfc1c32048f57 100644
--- a/lib/auth/keystore/pkcs11.go
+++ b/lib/auth/keystore/pkcs11.go
@@ -153,13 +153,13 @@ func (p *pkcs11KeyStore) generateRSA(ctx context.Context, options ...RSAKeyOptio
 		<-p.semaphore
 	}()
 
-	p.log.Debug("Creating new HSM keypair")
-
 	id, err := p.findUnusedID()
 	if err != nil {
 		return nil, nil, trace.Wrap(err)
 	}
 
+	p.log.Debugf("Creating new HSM keypair %v", id)
+
 	ckaID, err := id.pkcs11Key(p.isYubiHSM)
 	if err != nil {
 		return nil, nil, trace.Wrap(err)
@@ -201,7 +201,7 @@ func (p *pkcs11KeyStore) getSignerWithoutPublicKey(ctx context.Context, rawKey [
 		return nil, trace.Wrap(err)
 	}
 	if signer == nil {
-		return nil, trace.NotFound("failed to find keypair for given id")
+		return nil, trace.NotFound("failed to find keypair with id %v", keyID)
 	}
 	return signer, nil
 }
@@ -308,6 +308,7 @@ func (p *pkcs11KeyStore) deleteUnusedKeys(ctx context.Context, activeKeys [][]by
 		if keyIsActive(signer) {
 			continue
 		}
+		p.log.Infof("Deleting unused key from HSM")
 		if err := signer.Delete(); err != nil {
 			// Key deletion is best-effort, log a warning on errors, and
 			// continue trying to delete other keys. Errors have been observed
diff --git a/lib/auth/keystore/testhelpers.go b/lib/auth/keystore/testhelpers.go
index 4cbe6b63d6141..a4f2c850e87ec 100644
--- a/lib/auth/keystore/testhelpers.go
+++ b/lib/auth/keystore/testhelpers.go
@@ -51,7 +51,7 @@ func HSMTestConfig(t *testing.T) Config {
 		t.Log("Running test with SoftHSM")
 		return cfg
 	}
-	t.Fatal("No HSM available for test")
+	t.Skip("No HSM available for test")
 	return Config{}
 }
 
diff --git a/lib/service/service.go b/lib/service/service.go
index 0562ffb81dd97..4fde5af3145cd 100644
--- a/lib/service/service.go
+++ b/lib/service/service.go
@@ -743,16 +743,24 @@ func waitAndReload(ctx context.Context, cfg servicecfg.Config, srv Process, newT
 		warnOnErr(srv.Close(), cfg.Log)
 		return nil, trace.Wrap(err, "failed to start a new service")
 	}
+
 	// Wait for the new server to report that it has started
 	// before shutting down the old one.
 	startTimeoutCtx, startCancel := context.WithTimeout(ctx, signalPipeTimeout)
 	defer startCancel()
+	go func() {
+		// Avoid waiting for TeleportReadyEvent if it will never fire.
+		newSrv.WaitForEvent(startTimeoutCtx, ServiceExitedWithErrorEvent)
+		startCancel()
+	}()
 	if _, err := newSrv.WaitForEvent(startTimeoutCtx, TeleportReadyEvent); err != nil {
 		warnOnErr(newSrv.Close(), cfg.Log)
 		warnOnErr(srv.Close(), cfg.Log)
 		return nil, trace.BadParameter("the new service has failed to start")
 	}
 	cfg.Log.Infof("New service has started successfully.")
+	startCancel()
+
 	shutdownTimeout := cfg.Testing.ShutdownTimeout
 	if shutdownTimeout == 0 {
 		// The default shutdown timeout is very generous to avoid disrupting
@@ -786,6 +794,7 @@ func waitAndReload(ctx context.Context, cfg servicecfg.Config, srv Process, newT
 	} else {
 		cfg.Log.Infof("The old service was successfully shut down gracefully.")
 	}
+
 	return newSrv, nil
 }
 
diff --git a/lib/utils/listener.go b/lib/utils/listener.go
index e12d51bede342..42922c59fe9c1 100644
--- a/lib/utils/listener.go
+++ b/lib/utils/listener.go
@@ -29,9 +29,11 @@ import (
 func GetListenerFile(listener net.Listener) (*os.File, error) {
 	switch t := listener.(type) {
 	case *net.TCPListener:
-		return t.File()
+		f, err := t.File()
+		return f, trace.Wrap(err)
 	case *net.UnixListener:
-		return t.File()
+		f, err := t.File()
+		return f, trace.Wrap(err)
 	}
 	return nil, trace.BadParameter("unsupported listener: %T", listener)
 }