diff --git a/crates/server/src/routes/config.rs b/crates/server/src/routes/config.rs
index 4504cb52..4fb33aad 100644
--- a/crates/server/src/routes/config.rs
+++ b/crates/server/src/routes/config.rs
@@ -88,12 +88,25 @@ async fn update_config(
 ) -> ResponseJson<ApiResponse<Config>> {
     let config_path = config_path();
 
+    // Get the current analytics_enabled state before updating
+    let old_analytics_enabled = {
+        let config = deployment.config().read().await;
+        config.analytics_enabled
+    };
+
     match save_config_to_file(&new_config, &config_path).await {
         Ok(_) => {
             let mut config = deployment.config().write().await;
             *config = new_config.clone();
             drop(config);
 
+            // If analytics was just enabled (changed from None/false to true), track session_start
+            if new_config.analytics_enabled == Some(true) && old_analytics_enabled != Some(true) {
+                deployment
+                    .track_if_analytics_allowed("session_start", serde_json::json!({}))
+                    .await;
+            }
+
             ResponseJson(ApiResponse::success(new_config))
         }
         Err(e) => ResponseJson(ApiResponse::error(&format!("Failed to save config: {}", e))),