diff --git a/lib/connection/connection_registry.dart b/lib/connection/connection_registry.dart
index df894293..eb692b47 100644
--- a/lib/connection/connection_registry.dart
+++ b/lib/connection/connection_registry.dart
@@ -42,14 +42,22 @@ class ConnectionRegistry {
 
   /// Insert or replace [connection]. If this is the first stored connection
   /// it is automatically marked default; re-upserting an existing row keeps
-  /// the row's current `isDefault` (so token/metadata refreshes don't clear
-  /// the default flag).
+  /// the row's current `isDefault` and `createdAt` (so token/metadata
+  /// refreshes don't clear the default flag or restamp creation order).
+  ///
+  /// Creation order is behaviour, not bookkeeping: it decides which
+  /// connection lends a profile its picture, and `remove` promotes the oldest
+  /// remaining row to default. Re-authenticating rebuilds the model with
+  /// `DateTime.now()` and reuses the same stable id, so without this the
+  /// originally-first connection would jump to last on every re-sign-in.
   Future<void> upsert(Connection connection) async {
     await _db.runIdentityMutation(() async {
       final existing = await (_db.select(_db.connections)..where((t) => t.id.equals(connection.id))).getSingleOrNull();
       final bool isDefault;
+      final int createdAt;
       if (existing != null) {
         isDefault = existing.isDefault;
+        createdAt = existing.createdAt;
       } else {
         final any =
             await (_db.selectOnly(_db.connections)
@@ -57,6 +65,7 @@ class ConnectionRegistry {
                   ..limit(1))
                 .getSingleOrNull();
         isDefault = any == null;
+        createdAt = connection.createdAt.millisecondsSinceEpoch;
       }
       final protectedConfig = await CredentialVault.protectConnectionConfig(
         connection.kind.id,
@@ -68,7 +77,7 @@ class ConnectionRegistry {
         displayName: Value(connection.displayName),
         configJson: Value(jsonEncode(protectedConfig)),
         isDefault: Value(isDefault),
-        createdAt: Value(connection.createdAt.millisecondsSinceEpoch),
+        createdAt: Value(createdAt),
         lastAuthenticatedAt: Value(connection.lastAuthenticatedAt?.millisecondsSinceEpoch),
       );
       await _db.into(_db.connections).insertOnConflictUpdate(row);
diff --git a/test/connection/connection_registry_test.dart b/test/connection/connection_registry_test.dart
index fda42bc4..1a50beac 100644
--- a/test/connection/connection_registry_test.dart
+++ b/test/connection/connection_registry_test.dart
@@ -20,7 +20,7 @@ Future<String?> _defaultConnectionId(AppDatabase db) async {
   return null;
 }
 
-JellyfinConnection _jellyfin({String id = 'srv-1', String userName = 'edde'}) {
+JellyfinConnection _jellyfin({String id = 'srv-1', String userName = 'edde', int createdAtMs = 1_000_000}) {
   return JellyfinConnection(
     id: id,
     baseUrl: 'https://jellyfin.local',
@@ -30,7 +30,7 @@ JellyfinConnection _jellyfin({String id = 'srv-1', String userName = 'edde'}) {
     userName: userName,
     accessToken: 'tok-$id',
     deviceId: 'dev-1',
-    createdAt: DateTime.fromMillisecondsSinceEpoch(1_000_000),
+    createdAt: DateTime.fromMillisecondsSinceEpoch(createdAtMs),
   );
 }
 
@@ -184,6 +184,28 @@ void main() {
       expect(await _defaultConnectionId(db), 'a');
     });
 
+    test('re-upsert preserves the original creation order', () async {
+      // Regression: creation order decides which connection lends a profile
+      // its picture (issue #1667) and which row `remove` promotes to default.
+      // Re-authenticating rebuilds the model with `DateTime.now()` under the
+      // same stable id, so an unguarded writer restamped the originally-first
+      // connection and shuffled it to last.
+      await registry.upsert(_jellyfin(id: 'first', createdAtMs: 1_000_000));
+      await registry.upsert(_jellyfin(id: 'second', createdAtMs: 2_000_000));
+
+      await registry.upsert(_jellyfin(id: 'first', createdAtMs: 9_000_000));
+
+      final list = await registry.list();
+      expect(list.map((c) => c.id).toList(), ['first', 'second']);
+      expect(list.first.createdAt, DateTime.fromMillisecondsSinceEpoch(1_000_000));
+    });
+
+    test('a genuinely new connection keeps the creation time it was built with', () async {
+      await registry.upsert(_jellyfin(id: 'a', createdAtMs: 5_000_000));
+
+      expect((await registry.list()).single.createdAt, DateTime.fromMillisecondsSinceEpoch(5_000_000));
+    });
+
     test('recordAuthSuccess updates lastAuthenticatedAt without losing config', () async {
       await registry.upsert(_jellyfin(id: 'a'));
       final at = DateTime.fromMillisecondsSinceEpoch(2_000_000);