diff --git a/apps/desktop/src/App.vue b/apps/desktop/src/App.vue
index 8d392f082..31cc105cc 100644
--- a/apps/desktop/src/App.vue
+++ b/apps/desktop/src/App.vue
@@ -756,6 +756,7 @@ function onLoginSuccess() {
 function initApp() {
   const t0 = performance.now();
   console.log("[STARTUP] initApp begin");
+  settingsStore.initDesktopSettings().catch(() => {});
   savedSqlStore
     .initFromStorage()
     .then(() => {
diff --git a/crates/dbx-core/src/storage.rs b/crates/dbx-core/src/storage.rs
index c24a234fa..8bf30874e 100644
--- a/crates/dbx-core/src/storage.rs
+++ b/crates/dbx-core/src/storage.rs
@@ -335,6 +335,7 @@ impl Storage {
             show_tray_icon: settings
                 .get("show_tray_icon")
                 .and_then(|value| value.as_bool())
+                .or_else(|| settings.get("run_in_background").and_then(|value| value.as_bool()))
                 .unwrap_or_else(|| DesktopSettings::default().show_tray_icon),
         })
     }
@@ -1079,14 +1080,14 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn desktop_settings_ignore_legacy_background_preference() {
+    async fn desktop_settings_fall_back_to_legacy_background_preference() {
         let path = temp_db_path("desktop-settings-legacy-background");
         let storage = Storage::open(&path).await.unwrap();
         let mut settings = serde_json::Map::new();
         settings.insert("run_in_background".to_string(), serde_json::Value::Bool(false));
         storage.save_app_settings_json(&settings).await.unwrap();
 
-        assert_eq!(storage.load_desktop_settings().await.unwrap(), DesktopSettings { show_tray_icon: true });
+        assert_eq!(storage.load_desktop_settings().await.unwrap(), DesktopSettings { show_tray_icon: false });
     }
 
     #[tokio::test]
diff --git a/packages/app-tests/desktopTraySettingsMigration.test.ts b/packages/app-tests/desktopTraySettingsMigration.test.ts
new file mode 100644
index 000000000..2f35b601f
--- /dev/null
+++ b/packages/app-tests/desktopTraySettingsMigration.test.ts
@@ -0,0 +1,9 @@
+import test from "node:test";
+import assert from "node:assert/strict";
+import { readFileSync } from "node:fs";
+
+test("desktop settings fall back to the legacy run_in_background preference during upgrades", () => {
+  const source = readFileSync("crates/dbx-core/src/storage.rs", "utf8");
+
+  assert.match(source, /\.or_else\(\|\| settings\.get\("run_in_background"\)\.and_then\(\|value\| value\.as_bool\(\)\)\)/);
+});
diff --git a/packages/app-tests/desktopTraySettingsStartup.test.ts b/packages/app-tests/desktopTraySettingsStartup.test.ts
new file mode 100644
index 000000000..f1e69c71b
--- /dev/null
+++ b/packages/app-tests/desktopTraySettingsStartup.test.ts
@@ -0,0 +1,9 @@
+import test from "node:test";
+import assert from "node:assert/strict";
+import { readFileSync } from "node:fs";
+
+test("app startup eagerly loads desktop settings so tray preference is not reset in the UI", () => {
+  const source = readFileSync("apps/desktop/src/App.vue", "utf8");
+
+  assert.match(source, /settingsStore\.initDesktopSettings\(\)\.catch\(\(\) => \{\}\);/);
+});