diff --git a/rust/connlib/socket-factory/src/lib.rs b/rust/connlib/socket-factory/src/lib.rs
index 7d0d0f910..9189dc20d 100644
--- a/rust/connlib/socket-factory/src/lib.rs
+++ b/rust/connlib/socket-factory/src/lib.rs
@@ -356,6 +356,9 @@ impl UdpSocket {
                         if e.raw_os_error().is_some_and(|e| e == libc::ENOBUFS)
                             && firezone_telemetry::feature_flags::map_enobufs_to_would_block() =>
                     {
+                        firezone_telemetry::analytics::feature_flag_called(
+                            "map-enobufs-to-wouldblock",
+                        );
                         tracing::debug!("Encountered ENOBUFS, treating as WouldBlock");
 
                         Err(io::Error::from(io::ErrorKind::WouldBlock))
diff --git a/rust/telemetry/src/analytics.rs b/rust/telemetry/src/analytics.rs
index 1c165d037..f9c0bc280 100644
--- a/rust/telemetry/src/analytics.rs
+++ b/rust/telemetry/src/analytics.rs
@@ -65,6 +65,36 @@ pub fn identify(release: String, account_slug: Option<String>) {
     });
 }
 
+pub fn feature_flag_called(name: impl Into<String>) {
+    let Some(env) = Telemetry::current_env() else {
+        tracing::debug!("Cannot send $feature_flag_called: Unknown env");
+        return;
+    };
+    let Some(distinct_id) = Telemetry::current_user() else {
+        tracing::debug!("Cannot send $feature_flag_called: Unknown user");
+        return;
+    };
+    let feature_flag = name.into();
+
+    RUNTIME.spawn({
+        async move {
+            if let Err(e) = capture(
+                "$feature_flag_called",
+                distinct_id,
+                env,
+                FeatureFlagCalledProperties {
+                    feature_flag,
+                    feature_flag_response: "true".to_owned(),
+                },
+            )
+            .await
+            {
+                tracing::debug!("Failed to log `$feature_flag_called` event: {e:#}");
+            }
+        }
+    });
+}
+
 async fn capture<P>(
     event: impl Into<String>,
     distinct_id: String,
@@ -137,3 +167,11 @@ struct PersonProperties {
     #[serde(rename = "$os")]
     os: String,
 }
+
+#[derive(serde::Serialize)]
+struct FeatureFlagCalledProperties {
+    #[serde(rename = "$feature_flag")]
+    feature_flag: String,
+    #[serde(rename = "$feature_flag_response")]
+    feature_flag_response: String,
+}