diff --git a/apps/desktop/src-tauri/src/backend.rs b/apps/desktop/src-tauri/src/backend.rs
index 4571aa3cbd..bc12ebdee6 100644
--- a/apps/desktop/src-tauri/src/backend.rs
+++ b/apps/desktop/src-tauri/src/backend.rs
@@ -76,7 +76,14 @@ where
                 let backend = backend.clone();
                 scope.add_event_processor(move |mut event| {
                     event.user = Some(sentry_user()).map(|mut user| {
-                        user.username = backend.user();
+                        let auth = backend.user();
+                        user.id = backend
+                            .analytics
+                            .as_ref()
+                            .zip(auth.clone())
+                            .map(|(a, u)| a.tracking_id(&u.into()))
+                            .or_else(|| Some(get_device_id()));
+                        user.username = auth;
                         user
                     });
 
@@ -126,11 +133,13 @@ fn initialize_sentry(dsn: &str) {
         // the safe side, make sure we blow up
         panic!("in the disco");
     }
+
+    sentry::configure_scope(|scope| scope.set_user(Some(sentry_user())));
 }
 
 fn sentry_user() -> sentry::User {
     sentry::User {
-        id: Some(get_device_id()),
+        other: [("device_id".to_string(), get_device_id().into())].into(),
         ..Default::default()
     }
 }
diff --git a/client/src/utils/services.ts b/client/src/utils/services.ts
index 2aff82eae6..5c7c8fac0b 100644
--- a/client/src/utils/services.ts
+++ b/client/src/utils/services.ts
@@ -34,7 +34,8 @@ export const initializeSentry = (envConfig: EnvConfig, release: string) => {
   });
 
   Sentry.setUser({
-    id: envConfig.device_id,
+    id: envConfig.tracking_id,
     username: envConfig.user_login,
+    device_id: envConfig.device_id,
   });
 };
diff --git a/server/bleep/src/lib.rs b/server/bleep/src/lib.rs
index 8a6482545f..0517dbc0fe 100644
--- a/server/bleep/src/lib.rs
+++ b/server/bleep/src/lib.rs
@@ -92,7 +92,7 @@ pub struct Application {
     cookie_key: axum_extra::extract::cookie::Key,
 
     /// Analytics backend -- may be unintialized
-    analytics: Option<Arc<analytics::RudderHub>>,
+    pub analytics: Option<Arc<analytics::RudderHub>>,
 }
 
 impl Application {
diff --git a/server/bleep/src/state.rs b/server/bleep/src/state.rs
index d4ba0369f8..9beecef654 100644
--- a/server/bleep/src/state.rs
+++ b/server/bleep/src/state.rs
@@ -65,10 +65,13 @@ impl<T: Serialize + DeserializeOwned + Default + Send + Sync> PersistedState<T>
 
     fn load_or(name: &'static str, source: &StateSource, val: T) -> Self {
         let path = source.directory().join(name).with_extension("json");
-        Self {
+        let new = Self {
             state: Arc::new(read_file(&path).unwrap_or(val)),
             path,
-        }
+        };
+
+        new.store().unwrap();
+        new
     }
 
     pub fn store(&self) -> Result<()> {
diff --git a/server/bleep/src/webserver/middleware.rs b/server/bleep/src/webserver/middleware.rs
index e25781a1a8..41e2fda749 100644
--- a/server/bleep/src/webserver/middleware.rs
+++ b/server/bleep/src/webserver/middleware.rs
@@ -12,6 +12,12 @@ use sentry::{Hub, SentryFutureExt};
 #[derive(Clone)]
 pub struct User(pub Option<String>);
 
+impl From<String> for User {
+    fn from(value: String) -> Self {
+        User(Some(value))
+    }
+}
+
 pub fn sentry_layer(router: Router) -> Router {
     router.layer(from_fn(sentry_layer_mw))
 }