diff --git a/.changelog/9519.txt b/.changelog/9519.txt
new file mode 100644
index 0000000000..204d6b806f
--- /dev/null
+++ b/.changelog/9519.txt
@@ -0,0 +1,3 @@
+```release-note:improvement
+server: use the presense of stored federation state data as a sign that we already activated the federation state feature flag
+```
diff --git a/agent/consul/helper_test.go b/agent/consul/helper_test.go
index 7373234369..468d28bcdb 100644
--- a/agent/consul/helper_test.go
+++ b/agent/consul/helper_test.go
@@ -186,6 +186,16 @@ func waitForNewACLReplication(t *testing.T, server *Server, expectedReplicationT
 	})
 }
 
+func waitForFederationStateFeature(t *testing.T, server *Server) {
+	t.Helper()
+
+	retry.Run(t, func(r *retry.R) {
+		require.True(r, server.DatacenterSupportsFederationStates())
+	})
+
+	require.True(t, server.DatacenterSupportsFederationStates())
+}
+
 func seeEachOther(a, b []serf.Member, addra, addrb string) bool {
 	return serfMembersContains(a, addrb) && serfMembersContains(b, addra)
 }
diff --git a/agent/consul/leader.go b/agent/consul/leader.go
index 0872a5b3b9..f8a875c9ec 100644
--- a/agent/consul/leader.go
+++ b/agent/consul/leader.go
@@ -1540,6 +1540,10 @@ func (s *Server) reapTombstones(index uint64) {
 	}
 }
 
+func (s *Server) setDatacenterSupportsFederationStates() {
+	atomic.StoreInt32(&s.dcSupportsFederationStates, 1)
+}
+
 func (s *Server) DatacenterSupportsFederationStates() bool {
 	if atomic.LoadInt32(&s.dcSupportsFederationStates) != 0 {
 		return true
@@ -1564,7 +1568,7 @@ func (s *Server) DatacenterSupportsFederationStates() bool {
 	s.router.CheckServers(s.config.Datacenter, state.update)
 
 	if state.supported && state.found {
-		atomic.StoreInt32(&s.dcSupportsFederationStates, 1)
+		s.setDatacenterSupportsFederationStates()
 		return true
 	}
 
diff --git a/agent/consul/leader_federation_state_ae.go b/agent/consul/leader_federation_state_ae.go
index 4e5a8a45b2..5adf08f347 100644
--- a/agent/consul/leader_federation_state_ae.go
+++ b/agent/consul/leader_federation_state_ae.go
@@ -17,6 +17,16 @@ const (
 )
 
 func (s *Server) startFederationStateAntiEntropy() {
+	// Check to see if we can skip waiting for serf feature detection below.
+	if !s.DatacenterSupportsFederationStates() {
+		_, fedStates, err := s.fsm.State().FederationStateList(nil)
+		if err != nil {
+			s.logger.Warn("Failed to check for existing federation states and activate the feature flag quicker; skipping this optimization", "error", err)
+		} else if len(fedStates) > 0 {
+			s.setDatacenterSupportsFederationStates()
+		}
+	}
+
 	if s.config.DisableFederationStateAntiEntropy {
 		return
 	}
diff --git a/agent/consul/leader_federation_state_ae_test.go b/agent/consul/leader_federation_state_ae_test.go
index 17d5bf0865..875de4848a 100644
--- a/agent/consul/leader_federation_state_ae_test.go
+++ b/agent/consul/leader_federation_state_ae_test.go
@@ -13,6 +13,83 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
+func TestLeader_FederationStateAntiEntropy_FeatureIsStickyEvenIfSerfTagsRegress(t *testing.T) {
+	if testing.Short() {
+		t.Skip("too slow for testing.Short")
+	}
+
+	t.Parallel()
+
+	// We test this by having two datacenters with one server each. They
+	// initially come up and pass the serf barrier, then we power them both
+	// off. We leave the primary off permanently, and then we stand up the
+	// secondary. Hopefully it should transition to allow federation states.
+
+	dir1, s1 := testServerWithConfig(t, func(c *Config) {
+		c.PrimaryDatacenter = "dc1"
+	})
+	defer os.RemoveAll(dir1)
+	defer s1.Shutdown()
+	codec := rpcClient(t, s1)
+	defer codec.Close()
+
+	waitForLeaderEstablishment(t, s1)
+
+	dir2, s2 := testServerWithConfig(t, func(c *Config) {
+		c.Datacenter = "dc2"
+		c.PrimaryDatacenter = "dc1"
+		c.FederationStateReplicationRate = 100
+		c.FederationStateReplicationBurst = 100
+		c.FederationStateReplicationApplyLimit = 1000000
+	})
+	defer os.RemoveAll(dir2)
+	defer s2.Shutdown()
+	codec2 := rpcClient(t, s2)
+	defer codec2.Close()
+
+	waitForLeaderEstablishment(t, s2)
+
+	// Create the WAN link
+	joinWAN(t, s2, s1)
+	waitForLeaderEstablishment(t, s1)
+	waitForLeaderEstablishment(t, s2)
+
+	waitForFederationStateFeature(t, s1)
+	waitForFederationStateFeature(t, s2)
+
+	// Wait for everybody's AE to complete.
+	retry.Run(t, func(r *retry.R) {
+		_, states, err := s1.fsm.State().FederationStateList(nil)
+		require.NoError(r, err)
+		require.Len(r, states, 2)
+	})
+
+	// Shutdown s1 and s2.
+	s1.Shutdown()
+	s2.Shutdown()
+
+	// Restart just s2
+
+	dir2new, s2new := testServerWithConfig(t, func(c *Config) {
+		c.Datacenter = "dc2"
+		c.PrimaryDatacenter = "dc1"
+		c.FederationStateReplicationRate = 100
+		c.FederationStateReplicationBurst = 100
+		c.FederationStateReplicationApplyLimit = 1000000
+
+		c.DataDir = s2.config.DataDir
+		c.NodeName = s2.config.NodeName
+		c.NodeID = s2.config.NodeID
+	})
+	defer os.RemoveAll(dir2new)
+	defer s2new.Shutdown()
+
+	waitForLeaderEstablishment(t, s2new)
+
+	// It should be able to transition without connectivity to the primary.
+	waitForFederationStateFeature(t, s2new)
+}
+
 func TestLeader_FederationStateAntiEntropy_BlockingQuery(t *testing.T) {
 	t.Parallel()