diff --git a/nomad/encrypter.go b/nomad/encrypter.go
index e6e05bcce79e..f13dc84be537 100644
--- a/nomad/encrypter.go
+++ b/nomad/encrypter.go
@@ -155,12 +155,33 @@ const keyIDHeader = "kid"
 // SignClaims signs the identity claim for the task and returns an
 // encoded JWT with both the claim and its signature
 func (e *Encrypter) SignClaims(claim *structs.IdentityClaims) (string, error) {
-	e.lock.RLock()
-	defer e.lock.RUnlock()
 
-	keyset, err := e.activeKeySetLocked()
+	getActiveKeyset := func() (*keyset, error) {
+		e.lock.RLock()
+		defer e.lock.RUnlock()
+		keyset, err := e.activeKeySetLocked()
+		return keyset, err
+	}
+
+	// If a key is rotated immediately following a leader election, plans that
+	// are in-flight may get signed before the new leader has the key. Allow for
+	// a short timeout-and-retry to avoid rejecting plans
+	keyset, err := getActiveKeyset()
 	if err != nil {
-		return "", err
+		ctx, cancel := context.WithTimeout(e.srv.shutdownCtx, 5*time.Second)
+		defer cancel()
+		for {
+			select {
+			case <-ctx.Done():
+				return "", err
+			default:
+				time.Sleep(50 * time.Millisecond)
+				keyset, err = getActiveKeyset()
+				if keyset != nil {
+					break
+				}
+			}
+		}
 	}
 
 	token := jwt.NewWithClaims(&jwt.SigningMethodEd25519{}, claim)
@@ -435,7 +456,10 @@ START:
 			return
 		default:
 			// Rate limit how often we attempt replication
-			limiter.Wait(ctx)
+			err := limiter.Wait(ctx)
+			if err != nil {
+				goto ERR_WAIT // rate limit exceeded
+			}
 
 			ws := store.NewWatchSet()
 			iter, err := store.RootKeyMetas(ws)
@@ -461,7 +485,8 @@ START:
 				getReq := &structs.KeyringGetRootKeyRequest{
 					KeyID: keyID,
 					QueryOptions: structs.QueryOptions{
-						Region: krr.srv.config.Region,
+						Region:        krr.srv.config.Region,
+						MinQueryIndex: keyMeta.ModifyIndex - 1,
 					},
 				}
 				getResp := &structs.KeyringGetRootKeyResponse{}
@@ -479,7 +504,7 @@ START:
 					getReq.AllowStale = true
 					for _, peer := range krr.getAllPeers() {
 						err = krr.srv.forwardServer(peer, "Keyring.Get", getReq, getResp)
-						if err == nil {
+						if err == nil && getResp.Key != nil {
 							break
 						}
 					}
diff --git a/nomad/encrypter_test.go b/nomad/encrypter_test.go
index b006b503d1cc..98d71758600c 100644
--- a/nomad/encrypter_test.go
+++ b/nomad/encrypter_test.go
@@ -123,8 +123,8 @@ func TestEncrypter_Restore(t *testing.T) {
 	}
 }
 
-// TestKeyringReplicator exercises key replication between servers
-func TestKeyringReplicator(t *testing.T) {
+// TestEncrypter_KeyringReplication exercises key replication between servers
+func TestEncrypter_KeyringReplication(t *testing.T) {
 
 	ci.Parallel(t)
 
@@ -267,6 +267,31 @@ func TestKeyringReplicator(t *testing.T) {
 	require.Eventually(t, checkReplicationFn(keyID3),
 		time.Second*5, time.Second,
 		"expected keys to be replicated to followers after election")
+
+	// Scenario: new members join the cluster
+
+	srv4, cleanupSRV4 := TestServer(t, func(c *Config) {
+		c.BootstrapExpect = 0
+		c.NumSchedulers = 0
+	})
+	defer cleanupSRV4()
+	srv5, cleanupSRV5 := TestServer(t, func(c *Config) {
+		c.BootstrapExpect = 0
+		c.NumSchedulers = 0
+	})
+	defer cleanupSRV5()
+
+	TestJoin(t, srv4, srv5)
+	TestJoin(t, srv5, srv1)
+	servers = []*Server{srv1, srv2, srv3, srv4, srv5}
+
+	testutil.WaitForLeader(t, srv4.RPC)
+	testutil.WaitForLeader(t, srv5.RPC)
+
+	require.Eventually(t, checkReplicationFn(keyID3),
+		time.Second*5, time.Second,
+		"expected new servers to get replicated keys")
+
 }
 
 func TestEncrypter_EncryptDecrypt(t *testing.T) {
diff --git a/nomad/keyring_endpoint.go b/nomad/keyring_endpoint.go
index 78d4808ce298..9b7e27ad90f7 100644
--- a/nomad/keyring_endpoint.go
+++ b/nomad/keyring_endpoint.go
@@ -264,7 +264,20 @@ func (k *Keyring) Get(args *structs.KeyringGetRootKeyRequest, reply *structs.Key
 				Key:  key,
 			}
 			reply.Key = rootKey
-			reply.Index = keyMeta.ModifyIndex
+
+			// Use the last index that affected the policy table
+			index, err := s.Index(state.TableRootKeyMeta)
+			if err != nil {
+				return err
+			}
+
+			// Ensure we never set the index to zero, otherwise a blocking query
+			// cannot be used.  We floor the index at one, since realistically
+			// the first write must have a higher index.
+			if index == 0 {
+				index = 1
+			}
+			reply.Index = index
 			return nil
 		},
 	}
diff --git a/nomad/leader.go b/nomad/leader.go
index 141b1df1035e..b6b2895fae67 100644
--- a/nomad/leader.go
+++ b/nomad/leader.go
@@ -303,9 +303,6 @@ func (s *Server) establishLeadership(stopCh chan struct{}) error {
 	// Initialize scheduler configuration.
 	schedulerConfig := s.getOrCreateSchedulerConfig()
 
-	// Create the first root key if it doesn't already exist
-	go s.initializeKeyring(stopCh)
-
 	// Initialize the ClusterID
 	_, _ = s.ClusterID()
 	// todo: use cluster ID for stuff, later!
@@ -350,6 +347,9 @@ func (s *Server) establishLeadership(stopCh chan struct{}) error {
 
 	// Further clean ups and follow up that don't block RPC consistency
 
+	// Create the first root key if it doesn't already exist
+	go s.initializeKeyring(stopCh)
+
 	// Restore the periodic dispatcher state
 	if err := s.restorePeriodicDispatcher(); err != nil {
 		return err
@@ -2005,7 +2005,7 @@ func (s *Server) initializeKeyring(stopCh <-chan struct{}) {
 			break
 		}
 	}
-	// we might have lost leadershuip during the version check
+	// we might have lost leadership during the version check
 	if !s.IsLeader() {
 		return
 	}