lib/data/repositories/email_repository_impl.dart

@@ -2963,6 +2963,20 @@ class EmailRepositoryImpl implements EmailRepository {
   }) async {
     if (query.length < 2) return [];
     final pattern = '%${query.toLowerCase()}%';
+
+    // Addresses we deliberately wrote to (sent folder) should appear before
+    // addresses that happened to email us (inbox/other folders).
+    final sentMailboxes = await (_db.select(_db.mailboxes)
+          ..where((t) {
+            Expression<bool> cond = t.role.equals('sent');
+            if (accountId != null) {
+              cond = t.accountId.equals(accountId) & cond;
+            }
+            return cond;
+          }))
+        .get();
+    final sentPaths = {for (final m in sentMailboxes) m.path};
+
     final rows = await (_db.select(_db.emails)
           ..where((t) {
             Expression<bool> cond = const Constant(true);
@@ -2977,11 +2991,22 @@ class EmailRepositoryImpl implements EmailRepository {
           ..limit(100))
         .get();
 
+    // Two passes: sent-folder rows first (prioritise recipients we chose),
+    // then other rows (senders who contacted us).
+    final sortedRows = [
+      ...rows.where((r) => sentPaths.contains(r.mailboxPath)),
+      ...rows.where((r) => !sentPaths.contains(r.mailboxPath)),
+    ];
+
     final seen = <String>{};
     final results = <model.EmailAddress>[];
     final lowerQuery = query.toLowerCase();
-    for (final row in rows) {
-      for (final jsonStr in [row.fromJson, row.toAddresses, row.ccJson]) {
+    for (final row in sortedRows) {
+      final isSent = sentPaths.contains(row.mailboxPath);
+      final fields = isSent
+          ? [row.toAddresses, row.ccJson, row.fromJson]
+          : [row.fromJson, row.toAddresses, row.ccJson];
+      for (final jsonStr in fields) {
         final list = jsonDecode(jsonStr) as List<dynamic>;
         for (final e in list) {
           final map = e as Map<String, dynamic>;

test/unit/email_repository_impl_test.dart

@@ -497,6 +497,60 @@ void main() {
       },
     );
 
+    test(
+      'searchAddresses prioritises sent-folder addresses over newer received',
+      () async {
+        final r = _makeRepos();
+        await r.accounts.addAccount(_account, 'pw');
+
+        // Register the Sent mailbox so searchAddresses knows its role.
+        await r.db.into(r.db.mailboxes).insert(
+              MailboxesCompanion.insert(
+                id: 'acc-1:Sent',
+                accountId: 'acc-1',
+                path: 'Sent',
+                name: 'Sent',
+                role: const Value('sent'),
+              ),
+            );
+
+        // Older sent email: user deliberately wrote to info@foo.de.
+        await r.db.into(r.db.emails).insert(
+              EmailsCompanion.insert(
+                id: 'acc-1:sent-1',
+                accountId: 'acc-1',
+                mailboxPath: 'Sent',
+                uid: 1,
+                receivedAt: DateTime(2025),
+                toAddresses: const Value(
+                  '[{"name":"Foo","email":"info@foo.de"}]',
+                ),
+              ),
+            );
+
+        // Newer received email: spam arrived today from info@spam.de.
+        await r.db.into(r.db.emails).insert(
+              EmailsCompanion.insert(
+                id: 'acc-1:inbox-1',
+                accountId: 'acc-1',
+                mailboxPath: 'INBOX',
+                uid: 2,
+                receivedAt: DateTime(2026),
+                fromJson: const Value(
+                  '[{"name":"Spam","email":"info@spam.de"}]',
+                ),
+              ),
+            );
+
+        // Even though spam is newer, the sent-folder address should win.
+        final results = await r.emails.searchAddresses(null, 'info');
+        expect(results.map((a) => a.email).toList(), [
+          'info@foo.de',
+          'info@spam.de',
+        ]);
+      },
+    );
+
     // ── IMAP method tests ────────────────────────────────────────────────────
 
     test(