diff --git a/enterprise/coderd/coderd.go b/enterprise/coderd/coderd.go
index 33732eea3d..ce2c0b069b 100644
--- a/enterprise/coderd/coderd.go
+++ b/enterprise/coderd/coderd.go
@@ -953,7 +953,7 @@ func (api *API) updateEntitlements(ctx context.Context) error {
 					coordinator = haCoordinator
 				}
 
-				api.replicaManager.SetCallback(func() {
+				api.replicaManager.AddCallback(func() {
 					// Only update DERP mesh if the built-in server is enabled.
 					if api.Options.DeploymentValues.DERP.Server.Enable {
 						addresses := make([]string, 0)
@@ -973,7 +973,7 @@ func (api *API) updateEntitlements(ctx context.Context) error {
 				if api.Options.DeploymentValues.DERP.Server.Enable {
 					api.derpMesh.SetAddresses([]string{}, false)
 				}
-				api.replicaManager.SetCallback(func() {
+				api.replicaManager.AddCallback(func() {
 					// If the amount of replicas change, so should our entitlements.
 					// This is to display a warning in the UI if the user is unlicensed.
 					_ = api.updateEntitlements(api.ctx)
diff --git a/enterprise/replicasync/replicasync.go b/enterprise/replicasync/replicasync.go
index f69db6ed94..fc37554477 100644
--- a/enterprise/replicasync/replicasync.go
+++ b/enterprise/replicasync/replicasync.go
@@ -122,10 +122,10 @@ type Manager struct {
 	closed      chan (struct{})
 	closeCancel context.CancelFunc
 
-	self     database.Replica
-	mutex    sync.Mutex
-	peers    []database.Replica
-	callback func()
+	self      database.Replica
+	mutex     sync.Mutex
+	peers     []database.Replica
+	callbacks []func()
 }
 
 func (m *Manager) ID() uuid.UUID {
@@ -312,7 +312,6 @@ func (m *Manager) syncReplicas(ctx context.Context) error {
 	}
 
 	m.mutex.Lock()
-	defer m.mutex.Unlock()
 	// nolint:gocritic // Updating a replica is a system function.
 	replica, err := m.db.UpdateReplica(dbauthz.AsSystemRestricted(ctx), database.UpdateReplicaParams{
 		ID:           m.self.ID,
@@ -330,6 +329,7 @@ func (m *Manager) syncReplicas(ctx context.Context) error {
 	})
 	if err != nil {
 		if !errors.Is(err, sql.ErrNoRows) {
+			m.mutex.Unlock()
 			return xerrors.Errorf("update replica: %w", err)
 		}
 		// self replica has been cleaned up, we must reinsert
@@ -348,6 +348,7 @@ func (m *Manager) syncReplicas(ctx context.Context) error {
 			Primary:         m.self.Primary,
 		})
 		if err != nil {
+			m.mutex.Unlock()
 			return xerrors.Errorf("update replica: %w", err)
 		}
 	}
@@ -355,12 +356,15 @@ func (m *Manager) syncReplicas(ctx context.Context) error {
 		// Publish an update occurred!
 		err = m.PublishUpdate()
 		if err != nil {
+			m.mutex.Unlock()
 			return xerrors.Errorf("publish replica update: %w", err)
 		}
 	}
 	m.self = replica
-	if m.callback != nil {
-		go m.callback()
+	callbacks := append([]func(){}, m.callbacks...)
+	m.mutex.Unlock()
+	for _, callback := range callbacks {
+		go callback()
 	}
 	return nil
 }
@@ -439,12 +443,12 @@ func (m *Manager) regionID() int32 {
 	return m.self.RegionID
 }
 
-// SetCallback sets a function to execute whenever new peers
+// AddCallback adds a function to execute whenever new peers
 // are refreshed or updated.
-func (m *Manager) SetCallback(callback func()) {
+func (m *Manager) AddCallback(callback func()) {
 	m.mutex.Lock()
-	defer m.mutex.Unlock()
-	m.callback = callback
+	m.callbacks = append(m.callbacks, callback)
+	m.mutex.Unlock()
 	// Instantly call the callback to inform replicas!
 	go callback()
 }
diff --git a/enterprise/replicasync/replicasync_test.go b/enterprise/replicasync/replicasync_test.go
index 0438db8e21..64116e2a30 100644
--- a/enterprise/replicasync/replicasync_test.go
+++ b/enterprise/replicasync/replicasync_test.go
@@ -207,6 +207,34 @@ func TestReplica(t *testing.T) {
 			return len(server.Regional()) == 0
 		}, testutil.WaitShort, testutil.IntervalFast)
 	})
+	t.Run("MultipleCallbacks", func(t *testing.T) {
+		t.Parallel()
+		dh := &derpyHandler{}
+		defer dh.requireOnlyDERPPaths(t)
+		srv := httptest.NewServer(dh)
+		defer srv.Close()
+		db, pubsub := dbtestutil.NewDB(t)
+		ctx, cancelCtx := context.WithCancel(context.Background())
+		defer cancelCtx()
+		server, err := replicasync.New(ctx, testutil.Logger(t), db, pubsub, &replicasync.Options{
+			RelayAddress: srv.URL,
+		})
+		require.NoError(t, err)
+		defer server.Close()
+
+		var first atomic.Int64
+		var second atomic.Int64
+		server.AddCallback(func() { first.Add(1) })
+		server.AddCallback(func() { second.Add(1) })
+		require.Eventually(t, func() bool {
+			return first.Load() >= 1 && second.Load() >= 1
+		}, testutil.WaitShort, testutil.IntervalFast)
+
+		require.NoError(t, server.UpdateNow(ctx))
+		require.Eventually(t, func() bool {
+			return first.Load() >= 2 && second.Load() >= 2
+		}, testutil.WaitShort, testutil.IntervalFast)
+	})
 	t.Run("TwentyConcurrent", func(t *testing.T) {
 		// Ensures that twenty concurrent replicas can spawn and all
 		// discover each other in parallel!
@@ -233,7 +261,7 @@ func TestReplica(t *testing.T) {
 			done := false
 
 			var m sync.Mutex
-			server.SetCallback(func() {
+			server.AddCallback(func() {
 				m.Lock()
 				defer m.Unlock()
 				if len(server.AllPrimary()) != count {