diff --git a/ios/Podfile.lock b/ios/Podfile.lock
index 4b3aae7..3525633 100644
--- a/ios/Podfile.lock
+++ b/ios/Podfile.lock
@@ -65,6 +65,8 @@ PODS:
     - onnxruntime-c (= 1.22.0)
   - package_info_plus (0.4.5):
     - Flutter
+  - pasteboard (0.0.1):
+    - Flutter
   - path_provider_foundation (0.0.1):
     - Flutter
     - FlutterMacOS
@@ -120,6 +122,7 @@ DEPENDENCIES:
   - home_widget (from `.symlinks/plugins/home_widget/ios`)
   - image_picker_ios (from `.symlinks/plugins/image_picker_ios/ios`)
   - package_info_plus (from `.symlinks/plugins/package_info_plus/ios`)
+  - pasteboard (from `.symlinks/plugins/pasteboard/ios`)
   - path_provider_foundation (from `.symlinks/plugins/path_provider_foundation/darwin`)
   - quick_actions_ios (from `.symlinks/plugins/quick_actions_ios/ios`)
   - record_ios (from `.symlinks/plugins/record_ios/ios`)
@@ -171,6 +174,8 @@ EXTERNAL SOURCES:
     :path: ".symlinks/plugins/image_picker_ios/ios"
   package_info_plus:
     :path: ".symlinks/plugins/package_info_plus/ios"
+  pasteboard:
+    :path: ".symlinks/plugins/pasteboard/ios"
   path_provider_foundation:
     :path: ".symlinks/plugins/path_provider_foundation/darwin"
   quick_actions_ios:
@@ -218,6 +223,7 @@ SPEC CHECKSUMS:
   onnxruntime-c: 7f778680e96145956c0a31945f260321eed2611a
   onnxruntime-objc: 83d28b87525bd971259a66e153ea32b5d023de19
   package_info_plus: af8e2ca6888548050f16fa2f1938db7b5a5df499
+  pasteboard: 49088aeb6119d51f976a421db60d8e1ab079b63c
   path_provider_foundation: bb55f6dbba17d0dccd6737fe6f7f34fbd0376880
   quick_actions_ios: 500fcc11711d9f646739093395c4ae8eec25f779
   record_ios: f75fa1d57f840012775c0e93a38a7f3ceea1a374
diff --git a/lib/features/chat/services/clipboard_attachment_service.dart b/lib/features/chat/services/clipboard_attachment_service.dart
index 0bcd429..9987e0a 100644
--- a/lib/features/chat/services/clipboard_attachment_service.dart
+++ b/lib/features/chat/services/clipboard_attachment_service.dart
@@ -1,6 +1,7 @@
 import 'dart:io';
 import 'dart:typed_data';
 import 'package:flutter/material.dart';
+import 'package:pasteboard/pasteboard.dart';
 import 'package:path_provider/path_provider.dart';
 import 'package:path/path.dart' as path;
 import 'file_attachment_service.dart';
@@ -9,6 +10,11 @@ import 'file_attachment_service.dart';
 ///
 /// This service converts pasted image data into [LocalAttachment] objects
 /// that integrate with the existing file attachment flow.
+///
+/// Uses the pasteboard package to read images from the system clipboard,
+/// which works across iOS, Android, and desktop platforms. On iOS 16+,
+/// this properly handles privacy restrictions that prevent standard paste
+/// operations from accessing image content.
 class ClipboardAttachmentService {
   /// Supported MIME types for image paste operations.
   static const Set<String> supportedImageMimeTypes = {
@@ -20,6 +26,95 @@ class ClipboardAttachmentService {
     'image/bmp',
   };
 
+  /// Reads an image from the system clipboard.
+  ///
+  /// Returns the image data as bytes if an image is present, null otherwise.
+  /// This uses the pasteboard package which properly interfaces with iOS's
+  /// UIPasteboard and works on other platforms as well.
+  Future<Uint8List?> getClipboardImage() async {
+    try {
+      final imageBytes = await Pasteboard.image;
+      return imageBytes;
+    } catch (e) {
+      debugPrint('ClipboardAttachmentService: Failed to read clipboard: $e');
+      return null;
+    }
+  }
+
+  /// Gets files from the clipboard (supported on desktop platforms).
+  ///
+  /// Returns a list of file paths if files are present, empty list otherwise.
+  Future<List<String>> getClipboardFiles() async {
+    try {
+      final files = await Pasteboard.files();
+      return files;
+    } catch (e) {
+      debugPrint(
+        'ClipboardAttachmentService: Failed to read clipboard files: $e',
+      );
+      return [];
+    }
+  }
+
+  /// Checks if the clipboard currently contains image data.
+  ///
+  /// Note: This reads the full image data from the clipboard because the
+  /// pasteboard package doesn't provide a lightweight check method. On iOS,
+  /// this also triggers the paste confirmation dialog.
+  Future<bool> hasClipboardImage() async {
+    try {
+      // The pasteboard package doesn't have a dedicated hasImage method,
+      // so we need to attempt to read the image. On iOS this is required
+      // for the user to see the paste confirmation.
+      final imageBytes = await Pasteboard.image;
+      return imageBytes != null && imageBytes.isNotEmpty;
+    } catch (e) {
+      debugPrint('ClipboardAttachmentService: Failed to check clipboard: $e');
+      return false;
+    }
+  }
+
+  /// Creates a [LocalAttachment] from the current clipboard image.
+  ///
+  /// Works on iOS, Android, and desktop platforms via the pasteboard package.
+  /// Returns null if no image is in the clipboard or if the operation fails.
+  Future<LocalAttachment?> createAttachmentFromClipboard() async {
+    final imageData = await getClipboardImage();
+    if (imageData == null || imageData.isEmpty) {
+      return null;
+    }
+
+    // Pasteboard returns PNG data by default
+    return createAttachmentFromImageData(
+      imageData: imageData,
+      mimeType: 'image/png',
+    );
+  }
+
+  /// Creates [LocalAttachment]s from clipboard files.
+  ///
+  /// Useful on desktop platforms where files can be copied directly.
+  Future<List<LocalAttachment>> createAttachmentsFromClipboardFiles() async {
+    final filePaths = await getClipboardFiles();
+    final attachments = <LocalAttachment>[];
+
+    for (final filePath in filePaths) {
+      try {
+        final file = File(filePath);
+        if (await file.exists()) {
+          final fileName = path.basename(file.path);
+          attachments.add(LocalAttachment(file: file, displayName: fileName));
+        }
+      } catch (e) {
+        debugPrint(
+          'ClipboardAttachmentService: Failed to process file $filePath: $e',
+        );
+      }
+    }
+
+    return attachments;
+  }
+
   /// Creates a [LocalAttachment] from pasted image data.
   ///
   /// The image data is saved to a temporary file with an appropriate extension
diff --git a/lib/features/chat/views/chat_page.dart b/lib/features/chat/views/chat_page.dart
index e88f721..19d979f 100644
--- a/lib/features/chat/views/chat_page.dart
+++ b/lib/features/chat/views/chat_page.dart
@@ -76,10 +76,6 @@ class _ChatPageState extends ConsumerState<ChatPage> {
     return name.trim();
   }
 
-  bool validateFileCount(int currentCount, int newCount, int maxCount) {
-    return (currentCount + newCount) <= maxCount;
-  }
-
   bool validateFileSize(int fileSize, int maxSizeMB) {
     return fileSize <= (maxSizeMB * 1024 * 1024);
   }
@@ -479,13 +475,6 @@ class _ChatPageState extends ConsumerState<ChatPage> {
       final attachments = await fileService.pickFiles();
       if (attachments.isEmpty) return;
 
-      // Validate file count
-      final currentFiles = ref.read(attachedFilesProvider);
-      if (!validateFileCount(currentFiles.length, attachments.length, 10)) {
-        if (!mounted) return;
-        return;
-      }
-
       // Validate file sizes
       for (final attachment in attachments) {
         final fileSize = await attachment.file.length();
@@ -570,13 +559,6 @@ class _ChatPageState extends ConsumerState<ChatPage> {
         return;
       }
 
-      // Validate file count (default 10 files limit like OpenWebUI)
-      final currentFiles = ref.read(attachedFilesProvider);
-      if (!validateFileCount(currentFiles.length, 1, 10)) {
-        if (!mounted) return;
-        return;
-      }
-
       // Add image to the attachment list
       ref.read(attachedFilesProvider.notifier).addFiles([attachment]);
       DebugLogger.log('Image added to attachment list', scope: 'chat/page');
@@ -613,15 +595,11 @@ class _ChatPageState extends ConsumerState<ChatPage> {
       scope: 'chat/page',
     );
 
-    // Validate file count (default 10 files limit like OpenWebUI)
-    final currentFiles = ref.read(attachedFilesProvider);
-    if (!validateFileCount(currentFiles.length, attachments.length, 10)) {
-      if (!mounted) return;
-      return;
-    }
+    // Add attachments to the list
+    ref.read(attachedFilesProvider.notifier).addFiles(attachments);
 
-    // Validate file sizes and process each attachment
-    final validAttachments = <LocalAttachment>[];
+    // Enqueue uploads via task queue for unified retry/progress
+    final activeConv = ref.read(activeConversationProvider);
     for (final attachment in attachments) {
       try {
         final fileSize = await attachment.file.length();
@@ -629,35 +607,6 @@ class _ChatPageState extends ConsumerState<ChatPage> {
           'Pasted file: ${attachment.displayName}, size: $fileSize bytes',
           scope: 'chat/page',
         );
-
-        // Validate file size (default 20MB limit like OpenWebUI)
-        if (!validateFileSize(fileSize, 20)) {
-          DebugLogger.log(
-            'Skipping oversized pasted file: ${attachment.displayName}',
-            scope: 'chat/page',
-          );
-          continue;
-        }
-
-        validAttachments.add(attachment);
-      } catch (e) {
-        DebugLogger.log(
-          'Error processing pasted attachment: $e',
-          scope: 'chat/page',
-        );
-      }
-    }
-
-    if (validAttachments.isEmpty) return;
-
-    // Add attachments to the list
-    ref.read(attachedFilesProvider.notifier).addFiles(validAttachments);
-
-    // Enqueue uploads via task queue for unified retry/progress
-    final activeConv = ref.read(activeConversationProvider);
-    for (final attachment in validAttachments) {
-      try {
-        final fileSize = await attachment.file.length();
         await ref
             .read(taskQueueProvider.notifier)
             .enqueueUploadMedia(
@@ -672,7 +621,7 @@ class _ChatPageState extends ConsumerState<ChatPage> {
     }
 
     DebugLogger.log(
-      'Added ${validAttachments.length} pasted attachment(s)',
+      'Added ${attachments.length} pasted attachment(s)',
       scope: 'chat/page',
     );
   }
diff --git a/lib/features/chat/widgets/modern_chat_input.dart b/lib/features/chat/widgets/modern_chat_input.dart
index 8b5f9b6..bf261f1 100644
--- a/lib/features/chat/widgets/modern_chat_input.dart
+++ b/lib/features/chat/widgets/modern_chat_input.dart
@@ -9,6 +9,7 @@ import 'package:flutter_riverpod/flutter_riverpod.dart';
 
 import 'dart:io' show Platform;
 import 'dart:async';
+import 'dart:typed_data';
 import 'dart:ui';
 import 'dart:math' as math;
 import '../providers/chat_providers.dart';
@@ -285,6 +286,90 @@ class _ModernChatInputState extends ConsumerState<ModernChatInput>
     }
   }
 
+  /// Handles pasting images/files from clipboard with pre-loaded image data.
+  ///
+  /// This avoids a second clipboard read by using data already fetched when
+  /// building the context menu.
+  Future<void> _handleClipboardPasteWithData(Uint8List imageData) async {
+    if (!widget.enabled) return;
+
+    final onPasted = widget.onPastedAttachments;
+    if (onPasted == null) return;
+
+    PlatformUtils.lightHaptic();
+
+    final attachment = await _clipboardService.createAttachmentFromImageData(
+      imageData: imageData,
+      mimeType: 'image/png',
+    );
+    if (attachment != null) {
+      await onPasted([attachment]);
+    }
+  }
+
+  /// Builds a custom context menu with standard options plus "Paste Image".
+  ///
+  /// The standard paste only works for text. This adds a "Paste Image"
+  /// option that uses the pasteboard package to read images from clipboard
+  /// on both iOS and Android. The option only appears when there's actually
+  /// an image in the clipboard.
+  Widget _buildContextMenu(
+    BuildContext context,
+    EditableTextState editableTextState,
+  ) {
+    final List<ContextMenuButtonItem> buttonItems = List.from(
+      editableTextState.contextMenuButtonItems,
+    );
+
+    // Only add "Paste Image" if we have a callback for pasted attachments
+    if (widget.onPastedAttachments == null) {
+      return AdaptiveTextSelectionToolbar.buttonItems(
+        anchors: editableTextState.contextMenuAnchors,
+        buttonItems: buttonItems,
+      );
+    }
+
+    // Check clipboard for images - the data is captured in the closure to
+    // avoid double-read and stale cache issues
+    return FutureBuilder<Uint8List?>(
+      future: _clipboardService.getClipboardImage(),
+      builder: (context, snapshot) {
+        final imageData = snapshot.data;
+        final hasImage = imageData != null && imageData.isNotEmpty;
+
+        if (hasImage) {
+          // Find the index of the standard Paste button to insert after it
+          final pasteIndex = buttonItems.indexWhere(
+            (item) => item.type == ContextMenuButtonType.paste,
+          );
+
+          // Capture imageData in closure to avoid re-reading clipboard
+          final pasteImageItem = ContextMenuButtonItem(
+            label: AppLocalizations.of(context)?.pasteImage ?? 'Paste Image',
+            onPressed: () {
+              // Close the context menu first
+              ContextMenuController.removeAny();
+              // Use the captured imageData directly
+              _handleClipboardPasteWithData(imageData);
+            },
+          );
+
+          // Insert after Paste if found, otherwise add at the end
+          if (pasteIndex >= 0) {
+            buttonItems.insert(pasteIndex + 1, pasteImageItem);
+          } else {
+            buttonItems.add(pasteImageItem);
+          }
+        }
+
+        return AdaptiveTextSelectionToolbar.buttonItems(
+          anchors: editableTextState.contextMenuAnchors,
+          buttonItems: buttonItems,
+        );
+      },
+    );
+  }
+
   void _insertNewline() {
     final text = _controller.text;
     TextSelection sel = _controller.selection;
@@ -1545,6 +1630,10 @@ class _ModernChatInputState extends ConsumerState<ModernChatInput>
                         .toList(),
                     onContentInserted: _handleContentInserted,
                   ),
+                  // Custom context menu with "Paste Image" option for iOS
+                  contextMenuBuilder: (context, editableTextState) {
+                    return _buildContextMenu(context, editableTextState);
+                  },
                   onSubmitted: (_) {
                     if (sendOnEnter) {
                       _sendMessage();
diff --git a/lib/l10n/app_de.arb b/lib/l10n/app_de.arb
index cd74f40..8e1bf87 100644
--- a/lib/l10n/app_de.arb
+++ b/lib/l10n/app_de.arb
@@ -128,6 +128,8 @@
   "file": "Datei",
   "photo": "Foto",
   "camera": "Kamera",
+  "pasteFromClipboard": "Einfügen",
+  "pasteImage": "Bild einfügen",
   "apiUnavailable": "API-Dienst nicht verfügbar",
   "unableToLoadImage": "Bild kann nicht geladen werden",
   "notAnImageFile": "Keine Bilddatei: {fileName}",
diff --git a/lib/l10n/app_en.arb b/lib/l10n/app_en.arb
index 30001dd..5ad189b 100644
--- a/lib/l10n/app_en.arb
+++ b/lib/l10n/app_en.arb
@@ -606,6 +606,14 @@
   "@camera": {
     "description": "Camera source label."
   },
+  "pasteFromClipboard": "Paste",
+  "@pasteFromClipboard": {
+    "description": "Action label to paste images or files from the clipboard."
+  },
+  "pasteImage": "Paste Image",
+  "@pasteImage": {
+    "description": "Context menu action to paste an image from the clipboard."
+  },
   "apiUnavailable": "API service not available",
   "@apiUnavailable": {
     "description": "Shown when backend API service is unavailable."
diff --git a/lib/l10n/app_es.arb b/lib/l10n/app_es.arb
index 530b240..9d55839 100644
--- a/lib/l10n/app_es.arb
+++ b/lib/l10n/app_es.arb
@@ -128,6 +128,8 @@
   "file": "Archivo",
   "photo": "Foto",
   "camera": "Cámara",
+  "pasteFromClipboard": "Pegar",
+  "pasteImage": "Pegar imagen",
   "apiUnavailable": "Servicio de API no disponible",
   "unableToLoadImage": "No se puede cargar la imagen",
   "notAnImageFile": "No es un archivo de imagen: {fileName}",
diff --git a/lib/l10n/app_fr.arb b/lib/l10n/app_fr.arb
index fe657b1..4210baf 100644
--- a/lib/l10n/app_fr.arb
+++ b/lib/l10n/app_fr.arb
@@ -128,6 +128,8 @@
   "file": "Fichier",
   "photo": "Photo",
   "camera": "Appareil photo",
+  "pasteFromClipboard": "Coller",
+  "pasteImage": "Coller l'image",
   "apiUnavailable": "Service API indisponible",
   "unableToLoadImage": "Impossible de charger l'image",
   "notAnImageFile": "Ce n'est pas un fichier image : {fileName}",
diff --git a/lib/l10n/app_it.arb b/lib/l10n/app_it.arb
index abf359e..1dc20d2 100644
--- a/lib/l10n/app_it.arb
+++ b/lib/l10n/app_it.arb
@@ -128,6 +128,8 @@
   "file": "File",
   "photo": "Foto",
   "camera": "Fotocamera",
+  "pasteFromClipboard": "Incolla",
+  "pasteImage": "Incolla immagine",
   "apiUnavailable": "Servizio API non disponibile",
   "unableToLoadImage": "Impossibile caricare l'immagine",
   "notAnImageFile": "Non è un file immagine: {fileName}",
diff --git a/lib/l10n/app_ko.arb b/lib/l10n/app_ko.arb
index 9b07977..49436cd 100644
--- a/lib/l10n/app_ko.arb
+++ b/lib/l10n/app_ko.arb
@@ -192,6 +192,8 @@
   "chooseDifferentFile": "다른 파일 선택",
   "photo": "사진",
   "camera": "카메라",
+  "pasteFromClipboard": "붙여넣기",
+  "pasteImage": "이미지 붙여넣기",
   "apiUnavailable": "API 서비스를 사용할 수 없습니다",
   "unableToLoadImage": "이미지를 불러올 수 없습니다",
   "notAnImageFile": "이미지 파일이 아닙니다: {fileName}",
diff --git a/lib/l10n/app_nl.arb b/lib/l10n/app_nl.arb
index 754d04a..d26423e 100644
--- a/lib/l10n/app_nl.arb
+++ b/lib/l10n/app_nl.arb
@@ -128,6 +128,8 @@
   "file": "Bestand",
   "photo": "Foto",
   "camera": "Camera",
+  "pasteFromClipboard": "Plakken",
+  "pasteImage": "Afbeelding plakken",
   "apiUnavailable": "API-service niet beschikbaar",
   "unableToLoadImage": "Kan afbeelding niet laden",
   "notAnImageFile": "Geen afbeeldingsbestand: {fileName}",
diff --git a/lib/l10n/app_ru.arb b/lib/l10n/app_ru.arb
index 2719705..643037c 100644
--- a/lib/l10n/app_ru.arb
+++ b/lib/l10n/app_ru.arb
@@ -128,6 +128,8 @@
   "file": "Файл",
   "photo": "Фото",
   "camera": "Камера",
+  "pasteFromClipboard": "Вставить",
+  "pasteImage": "Вставить изображение",
   "apiUnavailable": "Служба API недоступна",
   "unableToLoadImage": "Не удалось загрузить изображение",
   "notAnImageFile": "Не является файлом изображения: {fileName}",
diff --git a/lib/l10n/app_zh.arb b/lib/l10n/app_zh.arb
index 7bc07ba..35d6eeb 100644
--- a/lib/l10n/app_zh.arb
+++ b/lib/l10n/app_zh.arb
@@ -128,6 +128,8 @@
   "file": "文件",
   "photo": "照片",
   "camera": "相机",
+  "pasteFromClipboard": "粘贴",
+  "pasteImage": "粘贴图片",
   "apiUnavailable": "API 服务不可用",
   "unableToLoadImage": "无法加载图像",
   "notAnImageFile": "不是图像文件：{fileName}",
diff --git a/lib/l10n/app_zh_Hant.arb b/lib/l10n/app_zh_Hant.arb
index 09e9662..4713d59 100644
--- a/lib/l10n/app_zh_Hant.arb
+++ b/lib/l10n/app_zh_Hant.arb
@@ -128,6 +128,8 @@
   "file": "文件",
   "photo": "照片",
   "camera": "相機",
+  "pasteFromClipboard": "貼上",
+  "pasteImage": "貼上圖片",
   "apiUnavailable": "API 服務不可用",
   "unableToLoadImage": "無法加載圖像",
   "notAnImageFile": "不是圖像文件：{fileName}",
diff --git a/pubspec.lock b/pubspec.lock
index 627087a..06583da 100644
--- a/pubspec.lock
+++ b/pubspec.lock
@@ -1061,6 +1061,14 @@ packages:
       url: "https://pub.dev"
     source: hosted
     version: "3.2.1"
+  pasteboard:
+    dependency: "direct main"
+    description:
+      name: pasteboard
+      sha256: "9ff73ada33f79a59ff91f6c01881fd4ed0a0031cfc4ae2d86c0384471525fca1"
+      url: "https://pub.dev"
+    source: hosted
+    version: "0.4.0"
   path:
     dependency: "direct main"
     description:
diff --git a/pubspec.yaml b/pubspec.yaml
index fedaaf6..14320ea 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -79,6 +79,7 @@ dependencies:
   html_unescape: ^2.0.0
   home_widget: ^0.8.1
   flutter_highlight: ^0.7.0
+  pasteboard: ^0.4.0
   
   # Clipboard functionality is available through flutter/services (part of Flutter SDK)