diff --git a/changes/issue-3591-fix-usage-stats b/changes/issue-3591-fix-usage-stats
new file mode 100644
index 000000000..c7a8ca689
--- /dev/null
+++ b/changes/issue-3591-fix-usage-stats
@@ -0,0 +1 @@
+* Fix anonymous usage statistics to send missing `numLabels` field
\ No newline at end of file
diff --git a/cmd/fleet/serve_test.go b/cmd/fleet/serve_test.go
index 236d85f1d..e2251d0b7 100644
--- a/cmd/fleet/serve_test.go
+++ b/cmd/fleet/serve_test.go
@@ -47,6 +47,7 @@ func TestMaybeSendStatistics(t *testing.T) {
 			NumUsers:                  99,
 			NumTeams:                  9,
 			NumPolicies:               0,
+			NumLabels:                 3,
 			SoftwareInventoryEnabled:  true,
 			VulnDetectionEnabled:      true,
 			SystemUsersEnabled:        true,
@@ -62,7 +63,7 @@ func TestMaybeSendStatistics(t *testing.T) {
 	err := trySendStatistics(context.Background(), ds, fleet.StatisticsFrequency, ts.URL, &fleet.LicenseInfo{Tier: "premium"})
 	require.NoError(t, err)
 	assert.True(t, recorded)
-	assert.Equal(t, `{"anonymousIdentifier":"ident","fleetVersion":"1.2.3","licenseTier":"premium","numHostsEnrolled":999,"numUsers":99,"numTeams":9,"numPolicies":0,"softwareInventoryEnabled":true,"vulnDetectionEnabled":true,"systemUsersEnabled":true,"hostsStatusWebHookEnabled":true}`, requestBody)
+	assert.Equal(t, `{"anonymousIdentifier":"ident","fleetVersion":"1.2.3","licenseTier":"premium","numHostsEnrolled":999,"numUsers":99,"numTeams":9,"numPolicies":0,"numLabels":3,"softwareInventoryEnabled":true,"vulnDetectionEnabled":true,"systemUsersEnabled":true,"hostsStatusWebHookEnabled":true}`, requestBody)
 }
 
 func TestMaybeSendStatisticsSkipsSendingIfNotNeeded(t *testing.T) {
diff --git a/server/datastore/mysql/labels.go b/server/datastore/mysql/labels.go
index ce645e6e0..bdbe4e878 100644
--- a/server/datastore/mysql/labels.go
+++ b/server/datastore/mysql/labels.go
@@ -775,3 +775,12 @@ func (d *Datastore) AsyncBatchUpdateLabelTimestamp(ctx context.Context, ids []ui
 		return ctxerr.Wrap(ctx, err, "update hosts.label_updated_at")
 	})
 }
+
+func amountLabelsDB(db sqlx.Queryer) (int, error) {
+	var amount int
+	err := sqlx.Get(db, &amount, `SELECT count(*) FROM labels`)
+	if err != nil {
+		return 0, err
+	}
+	return amount, nil
+}
diff --git a/server/datastore/mysql/statistics.go b/server/datastore/mysql/statistics.go
index 0fa0ba088..237188820 100644
--- a/server/datastore/mysql/statistics.go
+++ b/server/datastore/mysql/statistics.go
@@ -32,7 +32,11 @@ func (d *Datastore) ShouldSendStatistics(ctx context.Context, frequency time.Dur
 	}
 	amountPolicies, err := amountPoliciesDB(d.writer)
 	if err != nil {
-		return fleet.StatisticsPayload{}, false, ctxerr.Wrap(ctx, err, "amount teams")
+		return fleet.StatisticsPayload{}, false, ctxerr.Wrap(ctx, err, "amount policies")
+	}
+	amountLabels, err := amountLabelsDB(d.writer)
+	if err != nil {
+		return fleet.StatisticsPayload{}, false, ctxerr.Wrap(ctx, err, "amount labels")
 	}
 	appConfig, err := d.AppConfig(ctx)
 	if err != nil {
@@ -59,6 +63,7 @@ func (d *Datastore) ShouldSendStatistics(ctx context.Context, frequency time.Dur
 				NumUsers:                  amountUsers,
 				NumTeams:                  amountTeams,
 				NumPolicies:               amountPolicies,
+				NumLabels:                 amountLabels,
 				SoftwareInventoryEnabled:  appConfig.HostSettings.EnableSoftwareInventory,
 				VulnDetectionEnabled:      appConfig.VulnerabilitySettings.DatabasesPath != "",
 				SystemUsersEnabled:        appConfig.HostSettings.EnableHostUsers,
@@ -82,8 +87,9 @@ func (d *Datastore) ShouldSendStatistics(ctx context.Context, frequency time.Dur
 		NumUsers:                  amountUsers,
 		NumTeams:                  amountTeams,
 		NumPolicies:               amountPolicies,
+		NumLabels:                 amountLabels,
 		SoftwareInventoryEnabled:  appConfig.HostSettings.EnableSoftwareInventory,
-		VulnDetectionEnabled:      &appConfig.VulnerabilitySettings.DatabasesPath != nil,
+		VulnDetectionEnabled:      appConfig.VulnerabilitySettings.DatabasesPath != "",
 		SystemUsersEnabled:        appConfig.HostSettings.EnableHostUsers,
 		HostsStatusWebHookEnabled: appConfig.WebhookSettings.HostStatusWebhook.Enable,
 	}, true, nil
diff --git a/server/datastore/mysql/statistics_test.go b/server/datastore/mysql/statistics_test.go
index 762228927..73df9a469 100644
--- a/server/datastore/mysql/statistics_test.go
+++ b/server/datastore/mysql/statistics_test.go
@@ -70,6 +70,15 @@ func testStatisticsShouldSend(t *testing.T, ds *Datastore) {
 	})
 	require.NoError(t, err)
 
+	// Create new label for test
+	_, err = ds.NewLabel(context.Background(), &fleet.Label{
+		Name:        "testlabel",
+		Query:       "select 1;",
+		Platform:    "darwin",
+		Description: "test label description",
+	})
+	require.NoError(t, err)
+
 	// Create new app config for test
 	config, err := ds.NewAppConfig(context.Background(), &fleet.AppConfig{
 		OrgInfo: fleet.OrgInfo{
@@ -80,7 +89,7 @@ func testStatisticsShouldSend(t *testing.T, ds *Datastore) {
 	require.NoError(t, err)
 	config.HostSettings.EnableSoftwareInventory = false
 	config.HostSettings.EnableHostUsers = false
-	config.VulnerabilitySettings.DatabasesPath = "foo/bar"
+	config.VulnerabilitySettings.DatabasesPath = ""
 	config.WebhookSettings.HostStatusWebhook.Enable = true
 
 	err = ds.SaveAppConfig(context.Background(), config)
@@ -99,9 +108,10 @@ func testStatisticsShouldSend(t *testing.T, ds *Datastore) {
 	assert.Equal(t, stats.NumUsers, 1)
 	assert.Equal(t, stats.NumTeams, 1)
 	assert.Equal(t, stats.NumPolicies, 1)
+	assert.Equal(t, stats.NumLabels, 1)
 	assert.Equal(t, stats.SoftwareInventoryEnabled, false)
 	assert.Equal(t, stats.SystemUsersEnabled, false)
-	assert.Equal(t, stats.VulnDetectionEnabled, true)
+	assert.Equal(t, stats.VulnDetectionEnabled, false)
 	assert.Equal(t, stats.HostsStatusWebHookEnabled, true)
 
 	firstIdentifier := stats.AnonymousIdentifier
diff --git a/server/fleet/statistics.go b/server/fleet/statistics.go
index d8ff4d271..1bdb0e883 100644
--- a/server/fleet/statistics.go
+++ b/server/fleet/statistics.go
@@ -10,6 +10,7 @@ type StatisticsPayload struct {
 	NumUsers                  int    `json:"numUsers"`
 	NumTeams                  int    `json:"numTeams"`
 	NumPolicies               int    `json:"numPolicies"`
+	NumLabels                 int    `json:"numLabels"`
 	SoftwareInventoryEnabled  bool   `json:"softwareInventoryEnabled"`
 	VulnDetectionEnabled      bool   `json:"vulnDetectionEnabled"`
 	SystemUsersEnabled        bool   `json:"systemUsersEnabled"`