TF-3864 Support pasting multiple address with multiple format mixed

Signed-off-by: dab246 <tdvu@linagora.com>

core/lib/utils/mail/named_address.dart

@@ -8,4 +8,7 @@ class NamedAddress with EquatableMixin {
 
   @override
   List<Object?> get props => [name, address];
+
+  @override
+  String toString() => name.isNotEmpty ? '$name <$address>' : address;
 }

core/lib/utils/string_convert.dart

@@ -139,15 +139,61 @@ class StringConvert {
     return isMarkdown || isAsciiArt;
   }
 
-  static NamedAddress? parseNamedAddress(String input) {
-    final regex = RegExp(r'''^(['"])(.+?)\1\s*<([^>\s]+)>$''');
-    final match = regex.firstMatch(input.trim());
-    if (match != null) {
-      final name = match.group(2)!;
-      final address = match.group(3)!;
+  static List<NamedAddress> extractNamedAddresses(String input) {
+    try {
+      if (input.contains('%')) {
+        input = Uri.decodeComponent(input);
+      }
 
-      return NamedAddress(name: name, address: address);
+      if (input.length % 4 == 0 &&
+          input.contains(RegExp(r'^[A-Za-z0-9+/=]+$'))) {
+        try {
+          input = utf8.decode(base64.decode(input));
+        } catch (_) {}
+      }
+
+      input = input.replaceAll('\n', ' ');
+      final results = <NamedAddress>[];
+
+      final pattern = RegExp(r'''(?:"([^"]+)"|'([^']+)'|)\s*<([^>]+)>''');
+
+      int currentIndex = 0;
+      final matches = pattern.allMatches(input).toList();
+
+      for (final match in matches) {
+        if (match.start > currentIndex) {
+          final between = input.substring(currentIndex, match.start);
+          results.addAll(_splitPlainAddresses(between, emailSeparatorPattern));
+        }
+
+        final name = match.group(1) ?? match.group(2) ?? '';
+        final email = match.group(3) ?? '';
+        results.add(NamedAddress(name: name.trim(), address: email.trim()));
+
+        currentIndex = match.end;
+      }
+
+      if (currentIndex < input.length) {
+        final tail = input.substring(currentIndex);
+        results.addAll(_splitPlainAddresses(tail, emailSeparatorPattern));
+      }
+      log('StringConvert::extractNamedAddresses:results = $results');
+      return results;
+    } catch (_) {
+      return [];
     }
-    return null;
+  }
+
+  static List<NamedAddress> _splitPlainAddresses(
+    String input,
+    String emailSeparatorPattern,
+  ) {
+    final separator = RegExp(emailSeparatorPattern);
+    return input
+        .split(separator)
+        .map((e) => e.trim())
+        .where((e) => e.isNotEmpty)
+        .map((e) => NamedAddress(name: '', address: e))
+        .toList();
   }
 }

core/test/utils/string_convert_test.dart

@@ -518,62 +518,302 @@ void main() {
     });
   });
 
-  group('StringConvert.parseNamedAddress', () {
-    test('Parses valid double-quoted input', () {
-      const input = '"John Doe" <john@example.com>';
-      final result = StringConvert.parseNamedAddress(input);
+  group('StringConvert.extractNamedAddresses', () {
+    test('Extracts plain emails', () {
+      const input = 'user1@example.com, user2@example.com; user3@example.com';
+      final result = StringConvert.extractNamedAddresses(input);
+
       expect(
         result,
-        NamedAddress(name: 'John Doe', address: 'john@example.com'),
+        equals([
+          NamedAddress(name: '', address: 'user1@example.com'),
+          NamedAddress(name: '', address: 'user2@example.com'),
+          NamedAddress(name: '', address: 'user3@example.com'),
+        ]),
       );
     });
 
-    test('Parses valid single-quoted input', () {
-      const input = "'Jane Smith' <jane123@abc.com>";
-      final result = StringConvert.parseNamedAddress(input);
+    test('Extracts quoted name and email', () {
+      const input = '"John Doe" <john@example.com>, "Jane" <jane@example.com>';
+      final result = StringConvert.extractNamedAddresses(input);
+
       expect(
         result,
-        NamedAddress(name: 'Jane Smith', address: 'jane123@abc.com'),
+        equals([
+          NamedAddress(name: 'John Doe', address: 'john@example.com'),
+          NamedAddress(name: 'Jane', address: 'jane@example.com'),
+        ]),
       );
     });
 
-    test('Keeps encoded values as-is (no decode)', () {
-      const input = '"John%20Doe" <john%40example.com>';
-      final result = StringConvert.parseNamedAddress(input);
+    test('Extracts mixed quoted and plain emails', () {
+      const input =
+          '"Alex" <alex@example.com>, user@example.com, "Sara" <sara@example.com>';
+      final result = StringConvert.extractNamedAddresses(input);
+
       expect(
         result,
-        NamedAddress(name: 'John%20Doe', address: 'john%40example.com'),
+        equals([
+          NamedAddress(name: 'Alex', address: 'alex@example.com'),
+          NamedAddress(name: '', address: 'user@example.com'),
+          NamedAddress(name: 'Sara', address: 'sara@example.com'),
+        ]),
       );
     });
 
-    test('Accepts whitespace between name and <address>', () {
-      const input = '"Name"     <value>';
-      final result = StringConvert.parseNamedAddress(input);
-      expect(result, NamedAddress(name: 'Name', address: 'value'));
+    test('Handles URL-encoded input', () {
+      const input =
+          'user1%40example.com%2C%20%22User%202%22%20%3Cuser2%40example.com%3E';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'user1@example.com'),
+          NamedAddress(name: 'User 2', address: 'user2@example.com'),
+        ]),
+      );
     });
 
-    test('Returns null for empty name', () {
-      const input = '"" <something>';
-      final result = StringConvert.parseNamedAddress(input);
-      expect(result, isNull);
+    test('Handles base64 encoded input', () {
+      const raw =
+          'user1@example.com user2@example.com "Name Three" <user3@example.com>';
+      final encoded = base64.encode(utf8.encode(raw));
+
+      final result = StringConvert.extractNamedAddresses(encoded);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'user1@example.com'),
+          NamedAddress(name: '', address: 'user2@example.com'),
+          NamedAddress(name: 'Name Three', address: 'user3@example.com'),
+        ]),
+      );
     });
 
-    test('Returns null for empty address', () {
-      const input = '"Valid" <>';
-      final result = StringConvert.parseNamedAddress(input);
-      expect(result, isNull);
+    test('Parses even invalid-looking emails without filtering', () {
+      const input = 'user@example.com, , ; not-an-email, "Bad" <not-email>';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'user@example.com'),
+          NamedAddress(name: '', address: 'not-an-email'),
+          NamedAddress(name: 'Bad', address: 'not-email'),
+        ]),
+      );
     });
 
-    test('Returns null for missing quotes', () {
-      const input = 'NoQuotes <abc>';
-      final result = StringConvert.parseNamedAddress(input);
-      expect(result, isNull);
+    test('Extracts duplicated emails without filtering', () {
+      const input =
+          '"A" <user@example.com>, user@EXAMPLE.com, "B" <USER@example.com>';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: 'A', address: 'user@example.com'),
+          NamedAddress(name: '', address: 'user@EXAMPLE.com'),
+          NamedAddress(name: 'B', address: 'USER@example.com'),
+        ]),
+      );
     });
 
-    test('Returns null for mismatched quotes', () {
-      const input = "'Mismatch\" <abc>";
-      final result = StringConvert.parseNamedAddress(input);
-      expect(result, isNull);
+    test('Handles single email', () {
+      const input = 'single@example.com';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'single@example.com'),
+        ]),
+      );
+    });
+
+    test('Handles input with newlines and spacing', () {
+      const input = '''
+        "John" <john@example.com>
+        user2@example.com ;
+        "Jane"   <jane@example.com>
+      ''';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: 'John', address: 'john@example.com'),
+          NamedAddress(name: '', address: 'user2@example.com'),
+          NamedAddress(name: 'Jane', address: 'jane@example.com'),
+        ]),
+      );
+    });
+
+    test('Parses mixed plain and quoted named emails', () {
+      const input =
+          'john.doe@example.com, jane.smith@example.com, alex.wilson@example.com, "ng van a" <ttnn@gmail.com>';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'john.doe@example.com'),
+          NamedAddress(name: '', address: 'jane.smith@example.com'),
+          NamedAddress(name: '', address: 'alex.wilson@example.com'),
+          NamedAddress(name: 'ng van a', address: 'ttnn@gmail.com'),
+        ]),
+      );
+    });
+
+    test('Parses multiple quoted named emails without delimiters', () {
+      const input =
+          '"ng van a" <ttnn@gmail.com> "ng van b" <ttnn1@gmail.com> "ng van c" <ttnn2@gmail.com> "ng van d" <ttnn3@gmail.com>';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: 'ng van a', address: 'ttnn@gmail.com'),
+          NamedAddress(name: 'ng van b', address: 'ttnn1@gmail.com'),
+          NamedAddress(name: 'ng van c', address: 'ttnn2@gmail.com'),
+          NamedAddress(name: 'ng van d', address: 'ttnn3@gmail.com'),
+        ]),
+      );
+    });
+
+    test('Handles semicolon after an email', () {
+      const input =
+          'john.doe@example.com;, jane.smith@example.com, alex.wilson@example.com';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'john.doe@example.com'),
+          NamedAddress(name: '', address: 'jane.smith@example.com'),
+          NamedAddress(name: '', address: 'alex.wilson@example.com'),
+        ]),
+      );
+    });
+
+    test('Handles completely empty string', () {
+      const input = '';
+      final result = StringConvert.extractNamedAddresses(input);
+      expect(result, isEmpty);
+    });
+
+    test('Handles only spaces and separators', () {
+      const inputs = [
+        '   ',
+        ',',
+        ';',
+        ',, ;;   ',
+        ' , ; ',
+        '   , ;  \n',
+        '\n',
+      ];
+
+      for (final input in inputs) {
+        final result = StringConvert.extractNamedAddresses(input);
+        expect(result, isEmpty, reason: 'Failed on input: "$input"');
+      }
+    });
+
+    test('Handles multiple delimiters between addresses', () {
+      const input = 'user1@example.com,,;  user2@example.com;;  user3@example.com';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'user1@example.com'),
+          NamedAddress(name: '', address: 'user2@example.com'),
+          NamedAddress(name: '', address: 'user3@example.com'),
+        ]),
+      );
+    });
+
+    test('Handles multiple delimiters and spaces', () {
+      const input =
+          'user1@example.com   ,   user2@example.com ;   user3@example.com';
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'user1@example.com'),
+          NamedAddress(name: '', address: 'user2@example.com'),
+          NamedAddress(name: '', address: 'user3@example.com'),
+        ]),
+      );
+    });
+
+    test('Handles a large number of addresses', () {
+      const base = 'user';
+      const domain = '@example.com';
+      final buffer = StringBuffer();
+
+      for (var i = 0; i < 1000; i++) {
+        buffer.write('$base$i$domain');
+        if (i != 999) buffer.write(', ');
+      }
+
+      final input = buffer.toString();
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(result.length, equals(1000));
+      expect(result.first, equals(NamedAddress(name: '', address: 'user0@example.com')));
+      expect(result.last, equals(NamedAddress(name: '', address: 'user999@example.com')));
+    });
+
+    test('Handles mixed valid, invalid, and named addresses correctly', () {
+      const input = '''
+        user@example.com, , ; not-an-email,
+        "Bad" <not-email>  "Bad-2" <not-email-2>,
+        'Bad-3' <not-email-3>;
+        'useb' <userb@example.com>
+      ''';
+
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'user@example.com'),
+          NamedAddress(name: '', address: 'not-an-email'),
+          NamedAddress(name: 'Bad', address: 'not-email'),
+          NamedAddress(name: 'Bad-2', address: 'not-email-2'),
+          NamedAddress(name: 'Bad-3', address: 'not-email-3'),
+          NamedAddress(name: 'useb', address: 'userb@example.com'),
+        ]),
+      );
+    });
+
+    test('Handles subaddressing with + and subfolders', () {
+      const input = '''
+        john.doe@example.com;
+        <userA+foldeA@example.com>;
+        <userA+folder Hello@exmaple.com>;
+        <userA+folderA.subFolderA@exmaple.com>;
+        <user+folder Hello.subFolder Hello@exmaple.com>;
+        alex.wilson@example.com
+      ''';
+
+      final result = StringConvert.extractNamedAddresses(input);
+
+      expect(
+        result,
+        equals([
+          NamedAddress(name: '', address: 'john.doe@example.com'),
+          NamedAddress(name: '', address: 'userA+foldeA@example.com'),
+          NamedAddress(name: '', address: 'userA+folder Hello@exmaple.com'),
+          NamedAddress(name: '', address: 'userA+folderA.subFolderA@exmaple.com'),
+          NamedAddress(name: '', address: 'user+folder Hello.subFolder Hello@exmaple.com'),
+          NamedAddress(name: '', address: 'alex.wilson@example.com'),
+        ]),
+      );
     });
   });
 }

lib/features/composer/presentation/extensions/auto_create_tag_for_recipients_extension.dart

@@ -1,14 +1,12 @@
-
-import 'package:core/utils/mail/mail_address.dart';
+import 'package:core/utils/app_logger.dart';
 import 'package:core/utils/string_convert.dart';
 import 'package:flutter/cupertino.dart';
 import 'package:jmap_dart_client/jmap/mail/email/email_address.dart';
 import 'package:model/email/prefix_email_address.dart';
-import 'package:model/extensions/email_address_extension.dart';
 import 'package:super_tag_editor/tag_editor.dart';
 import 'package:tmail_ui_user/features/composer/presentation/composer_controller.dart';
-import 'package:tmail_ui_user/features/composer/presentation/extensions/mail_address_extension.dart';
-import 'package:tmail_ui_user/features/composer/presentation/extensions/named_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/list_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/list_named_address_extension.dart';
 
 extension AutoCreateTagForRecipientsExtension on ComposerController {
 
@@ -42,36 +40,28 @@ extension AutoCreateTagForRecipientsExtension on ComposerController {
   };
 
   void autoCreateEmailTagForType(PrefixEmailAddress type, String input) {
-    final namedAddress = StringConvert.parseNamedAddress(input);
-    Set<String> addressSet = {};
+    final namedAddresses = StringConvert.extractNamedAddresses(input);
+    List<EmailAddress> newListEmailAddress = [];
+    final existingEmailList = _emailLists[type]!;
 
-    if (namedAddress == null) {
-      addressSet = StringConvert.extractEmailAddress(input).toSet();
-      if (addressSet.isEmpty) return;
+    if (namedAddresses.isNotEmpty) {
+      final emailAddressListFromNamed = namedAddresses
+          .toFilteredEmailAddressList(existingEmailList);
+      log('$runtimeType::autoCreateEmailTagForType: Create email tag from named address list with length ${emailAddressListFromNamed.length}');
+      newListEmailAddress = emailAddressListFromNamed;
     }
 
-    final emailList = _emailLists[type]!;
-    final keyEditor = _emailEditors[type]!;
-    List<EmailAddress> listEmailAddress = [];
-
-    final emailSet = emailList.map((email) => email.emailAddress).toSet();
-
-    if (namedAddress != null && !emailSet.contains(namedAddress.address)) {
-      listEmailAddress.add(namedAddress.toEmailAddress());
-    } else if (addressSet.isNotEmpty) {
-      final listEmailAddressRecord = addressSet
-        .map(_generateEmailAddressFromString)
-        .toList();
-
-      listEmailAddress = listEmailAddressRecord
-        .where((emailRecord) => !emailSet.contains(emailRecord.$1))
-        .map((emailRecord) => emailRecord.$2)
-        .toList();
+    if (newListEmailAddress.isEmpty) {
+      List<String> addresses = StringConvert.extractEmailAddress(input);
+      final emailAddressListFromAddress =
+          addresses.toFilteredEmailAddressList(existingEmailList);
+      log('$runtimeType::autoCreateEmailTagForType: Create email tag from address list with length ${emailAddressListFromAddress.length}');
+      newListEmailAddress = emailAddressListFromAddress;
     }
 
-    if (listEmailAddress.isEmpty) return;
+    if (newListEmailAddress.isEmpty) return;
 
-    emailList.addAll(listEmailAddress);
+    existingEmailList.addAll(newListEmailAddress);
 
     if (!isInitialRecipient.value) {
       isInitialRecipient.value = true;
@@ -80,19 +70,11 @@ extension AutoCreateTagForRecipientsExtension on ComposerController {
 
     updateStatusEmailSendButton();
 
+    final keyEditor = _emailEditors[type]!;
     keyEditor.currentState?.resetTextField();
     Future.delayed(
       const Duration(milliseconds: 300),
       keyEditor.currentState?.closeSuggestionBox,
     );
   }
-
-  (String email, EmailAddress emailAddress) _generateEmailAddressFromString(String input) {
-    try {
-      final mailAddress = MailAddress.validateAddress(input);
-      return (mailAddress.asEncodedString(), mailAddress.asEmailAddress());
-    } catch (e) {
-      return (input, EmailAddress(null, input));
-    }
-  }
 }

lib/features/composer/presentation/extensions/list_address_extension.dart

@@ -0,0 +1,38 @@
+import 'package:core/utils/mail/mail_address.dart';
+import 'package:jmap_dart_client/jmap/mail/email/email_address.dart';
+import 'package:model/extensions/email_address_extension.dart';
+import 'package:model/extensions/list_email_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/mail_address_extension.dart';
+
+extension ListAddressExtension on List<String> {
+  List<EmailAddress> toFilteredEmailAddressList(
+    List<EmailAddress> existingEmails,
+  ) {
+    final existingEmailSet = existingEmails.toNormalizedEmailSet();
+
+    final seen = <String>{};
+    final result = <EmailAddress>[];
+
+    for (final address in this) {
+      final emailAddress = _validateToEmailAddress(address);
+      final lowerAddress = emailAddress.emailAddress.toLowerCase();
+
+      if (existingEmailSet.contains(lowerAddress) || !seen.add(lowerAddress)) {
+        continue;
+      }
+
+      result.add(emailAddress);
+    }
+
+    return result;
+  }
+
+  EmailAddress _validateToEmailAddress(String address) {
+    try {
+      final mailAddress = MailAddress.validateAddress(address);
+      return mailAddress.asEmailAddress();
+    } catch (_) {
+      return EmailAddress(null, address);
+    }
+  }
+}

lib/features/composer/presentation/extensions/list_named_address_extension.dart

@@ -0,0 +1,17 @@
+import 'package:core/utils/mail/named_address.dart';
+import 'package:jmap_dart_client/jmap/mail/email/email_address.dart';
+import 'package:model/extensions/list_email_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/named_address_extension.dart';
+
+extension ListNamedAddressExtension on List<NamedAddress> {
+  List<EmailAddress> toFilteredEmailAddressList(
+    List<EmailAddress> existingEmails,
+  ) {
+    final existingEmailSet = existingEmails.toNormalizedEmailSet();
+    final seen = <String>{};
+    return where((named) {
+      final normalized = named.normalizedAddress;
+      return !existingEmailSet.contains(normalized) && seen.add(normalized);
+    }).map((named) => named.validateToEmailAddress()).toList();
+  }
+}

lib/features/composer/presentation/extensions/named_address_extension.dart

@@ -1,7 +1,25 @@
-
+import 'package:core/utils/mail/mail_address.dart';
 import 'package:core/utils/mail/named_address.dart';
 import 'package:jmap_dart_client/jmap/mail/email/email_address.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/mail_address_extension.dart';
 
 extension NamedAddressExtension on NamedAddress {
+  bool get isValid => name.isNotEmpty && address.isNotEmpty;
+
+  String get normalizedAddress => address.toLowerCase();
+
   EmailAddress toEmailAddress() => EmailAddress(name, address);
+
+  EmailAddress validateToEmailAddress() {
+    try {
+      if (isValid) {
+        return toEmailAddress();
+      } else {
+        final mailAddress = MailAddress.validateAddress(address);
+        return mailAddress.asEmailAddress();
+      }
+    } catch (_) {
+      return toEmailAddress();
+    }
+  }
 }

lib/features/composer/presentation/widgets/recipient_composer_widget.dart

@@ -18,7 +18,8 @@ import 'package:model/email/prefix_email_address.dart';
 import 'package:model/extensions/email_address_extension.dart';
 import 'package:model/mailbox/expand_mode.dart';
 import 'package:super_tag_editor/tag_editor.dart';
-import 'package:tmail_ui_user/features/composer/presentation/extensions/named_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/list_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/list_named_address_extension.dart';
 import 'package:tmail_ui_user/features/composer/presentation/extensions/prefix_email_address_extension.dart';
 import 'package:tmail_ui_user/features/composer/presentation/extensions/mail_address_extension.dart';
 import 'package:tmail_ui_user/features/composer/presentation/model/draggable_email_address.dart';
@@ -558,34 +559,33 @@ class _RecipientComposerWidgetState extends State<RecipientComposerWidget> {
   ) => _createMailTag(value, stateSetter);
 
   void _createMailTag(String value, StateSetter stateSetter) {
-    final namedAddress = StringConvert.parseNamedAddress(value.trim());
-    if (namedAddress != null) {
-      if (!_isDuplicatedRecipient(namedAddress.address)) {
+    final valueTrimmed = value.trim();
+    final namedAddresses = StringConvert.extractNamedAddresses(valueTrimmed);
+    if (namedAddresses.isNotEmpty) {
+      final emailAddressListFromNamed = namedAddresses
+          .toFilteredEmailAddressList(_currentListEmailAddress);
+      log('$runtimeType::_createMailTag: Create email tag from named address list with length ${emailAddressListFromNamed.length}');
+      if (emailAddressListFromNamed.isNotEmpty) {
         stateSetter(
-          () => _currentListEmailAddress.add(namedAddress.toEmailAddress()),
+          () => _currentListEmailAddress.addAll(emailAddressListFromNamed),
         );
         _updateListEmailAddressAction();
       }
       return;
     }
 
-    final listString = StringConvert.extractEmailAddress(value.trim()).toSet();
+    List<String> addresses = StringConvert.extractEmailAddress(valueTrimmed);
+    final emailAddressListFromAddress =
+      addresses.toFilteredEmailAddressList(_currentListEmailAddress);
+    log('$runtimeType::_createMailTag: Create email tag from address list with length ${emailAddressListFromAddress.length}');
 
-    if (listString.isEmpty && !_isDuplicatedRecipient(value)) {
+    if (emailAddressListFromAddress.isNotEmpty) {
+      stateSetter(
+        () => _currentListEmailAddress.addAll(emailAddressListFromAddress),
+      );
+      _updateListEmailAddressAction();
+    } else if (!_isDuplicatedRecipient(valueTrimmed)) {
       _onEmailAddressReceived(value, stateSetter);
-    } else if (listString.isNotEmpty) {
-      final listStringNotExist = listString
-        .where((text) => !_isDuplicatedRecipient(text))
-        .toList();
-
-      if (listStringNotExist.isNotEmpty) {
-        final listAddress = listStringNotExist
-          .map((text) => EmailAddress(null, text))
-          .toList();
-        
-        stateSetter(() => _currentListEmailAddress.addAll(listAddress));
-        _updateListEmailAddressAction();
-      }
     }
   }
 

model/lib/extensions/list_email_address_extension.dart

@@ -69,6 +69,9 @@ extension SetEmailAddressExtension on Set<EmailAddress>? {
 extension ListEmailAddressExtension on List<EmailAddress> {
   Set<String> asSetAddress() => map((emailAddress) => emailAddress.emailAddress).toSet();
 
+  Set<String> toNormalizedEmailSet() =>
+      map((e) => e.email?.toLowerCase()).whereType<String>().toSet();
+
   List<EmailAddress> removeInvalidEmails(String username) {
     final Set<String> seenEmails = {};
     return where((email) {

test/features/composer/presentation/extensions/list_address_extension_test.dart

@@ -0,0 +1,93 @@
+import 'package:flutter_test/flutter_test.dart';
+import 'package:jmap_dart_client/jmap/mail/email/email_address.dart';
+import 'package:model/extensions/email_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/list_address_extension.dart';
+
+void main() {
+  group('ListAddressExtension.toFilteredEmailAddressList', () {
+    test('removes existing emails and duplicates', () {
+      final addresses = [
+        'a@example.com',
+        'b@example.com',
+        'B@EXAMPLE.COM', // duplicate in different case
+        'c@example.com',
+      ];
+      final existingEmails = [
+        EmailAddress('B', 'b@example.com'),
+        EmailAddress('X', 'x@example.com'),
+      ];
+
+      final result = addresses.toFilteredEmailAddressList(existingEmails);
+
+      expect(result.map((e) => e.emailAddress), [
+        'a@example.com',
+        'c@example.com',
+      ]);
+    });
+
+    test('keeps all unique and non-existing emails', () {
+      final addresses = [
+        'a@example.com',
+        'b@example.com',
+        'c@example.com',
+      ];
+      final existingEmails = [
+        EmailAddress('Someone', 'z@example.com'),
+      ];
+
+      final result = addresses.toFilteredEmailAddressList(existingEmails);
+
+      expect(result.map((e) => e.emailAddress), [
+        'a@example.com',
+        'b@example.com',
+        'c@example.com',
+      ]);
+    });
+
+    test('skips invalid emails', () {
+      final addresses = [
+        'invalid-email',
+        'valid@example.com',
+      ];
+      final existingEmails = <EmailAddress>[];
+
+      final result = addresses.toFilteredEmailAddressList(existingEmails);
+
+      expect(result.length, 2);
+      expect(result[0].emailAddress, 'invalid-email');
+      expect(result[0].name, isNull);
+      expect(result[1].emailAddress, 'valid@example.com');
+    });
+
+    test('removes duplicates within the list', () {
+      final addresses = [
+        'a@example.com',
+        'A@EXAMPLE.COM', // duplicate in different case
+        'b@example.com',
+        'b@example.com',
+      ];
+      final existingEmails = <EmailAddress>[];
+
+      final result = addresses.toFilteredEmailAddressList(existingEmails);
+
+      expect(result.map((e) => e.emailAddress), [
+        'a@example.com',
+        'b@example.com',
+      ]);
+    });
+
+    test('removes addresses matching normalized existingEmails', () {
+      final addresses = [
+        '  A@Example.Com  ',
+        'b@example.com',
+      ];
+      final existingEmails = [
+        EmailAddress('A', 'a@example.com'),
+      ];
+
+      final result = addresses.toFilteredEmailAddressList(existingEmails);
+
+      expect(result.map((e) => e.emailAddress), ['b@example.com']);
+    });
+  });
+}

test/features/composer/presentation/extensions/list_named_address_extension_test.dart

@@ -0,0 +1,76 @@
+import 'package:core/utils/mail/named_address.dart';
+import 'package:flutter_test/flutter_test.dart';
+import 'package:jmap_dart_client/jmap/mail/email/email_address.dart';
+import 'package:model/extensions/email_address_extension.dart';
+import 'package:tmail_ui_user/features/composer/presentation/extensions/list_named_address_extension.dart';
+
+void main() {
+  group('ListNamedAddressExtension.toFilteredEmailAddressList', () {
+    test('filters out emails already in existingEmails list', () {
+      final namedList = [
+        NamedAddress(name: 'A', address: 'a@example.com'),
+        NamedAddress(name: 'B', address: 'b@example.com'),
+        NamedAddress(name: 'C', address: 'c@example.com'),
+      ];
+
+      final existingEmails = [
+        EmailAddress('B', 'b@example.com'),
+      ];
+
+      final result = namedList.toFilteredEmailAddressList(existingEmails);
+
+      expect(
+        result.map((e) => e.emailAddress),
+        containsAll(['a@example.com', 'c@example.com']),
+      );
+      expect(
+        result.map((e) => e.emailAddress),
+        isNot(contains('b@example.com')),
+      );
+    });
+
+    test('removes duplicate emails within the same list', () {
+      final namedList = [
+        NamedAddress(name: 'A1', address: 'a@example.com'),
+        NamedAddress(name: 'A2', address: 'A@Example.com'),
+        // Duplicate with different case
+        NamedAddress(name: 'B', address: 'b@example.com'),
+      ];
+
+      final result = namedList.toFilteredEmailAddressList([]);
+
+      expect(result.length, 2);
+      expect(
+        result.map((e) => e.emailAddress),
+        containsAll(['a@example.com', 'b@example.com']),
+      );
+    });
+
+    test('returns empty list if all emails are either existing or duplicates',
+        () {
+      final namedList = [
+        NamedAddress(name: 'A', address: 'a@example.com'),
+        NamedAddress(name: 'A2', address: 'A@Example.com'),
+      ];
+
+      final existingEmails = [
+        EmailAddress('Existing A', 'a@example.com'),
+      ];
+
+      final result = namedList.toFilteredEmailAddressList(existingEmails);
+
+      expect(result, isEmpty);
+    });
+
+    test('handles emails with empty name fields', () {
+      final namedList = [
+        NamedAddress(name: '', address: 'test@example.com'),
+      ];
+
+      final result = namedList.toFilteredEmailAddressList([]);
+
+      expect(result.length, 1);
+      expect(result.first.emailAddress, 'test@example.com');
+    });
+  });
+}