diff --git a/electron/ipc/system.ts b/electron/ipc/system.ts
index befd1b7..ac0c5c3 100644
--- a/electron/ipc/system.ts
+++ b/electron/ipc/system.ts
@@ -1,5 +1,6 @@
 import {
   app,
+  clipboard,
   desktopCapturer,
   dialog,
   ipcMain,
@@ -7,6 +8,8 @@ import {
 } from 'electron';
 import * as fs from 'fs';
 import * as fsp from 'fs/promises';
+import * as path from 'path';
+import { fileURLToPath } from 'url';
 import { getDesktopSettingsSnapshot, updateDesktopSettings } from '../desktop-settings';
 import {
   activateLinuxScreenShareAudioRouting,
@@ -16,6 +19,166 @@ import {
   stopLinuxScreenShareMonitorCapture
 } from '../audio/linux-screen-share-routing';
 
+const DEFAULT_MIME_TYPE = 'application/octet-stream';
+const FILE_CLIPBOARD_FORMATS = [
+  'x-special/gnome-copied-files',
+  'text/uri-list',
+  'public.file-url',
+  'FileNameW'
+] as const;
+const MIME_TYPES_BY_EXTENSION: Record<string, string> = {
+  '.7z': 'application/x-7z-compressed',
+  '.aac': 'audio/aac',
+  '.avi': 'video/x-msvideo',
+  '.bmp': 'image/bmp',
+  '.csv': 'text/csv',
+  '.doc': 'application/msword',
+  '.docx': 'application/vnd.openxmlformats-officedocument.wordprocessingml.document',
+  '.gif': 'image/gif',
+  '.gz': 'application/gzip',
+  '.heic': 'image/heic',
+  '.jpeg': 'image/jpeg',
+  '.jpg': 'image/jpeg',
+  '.json': 'application/json',
+  '.m4a': 'audio/mp4',
+  '.md': 'text/markdown',
+  '.mov': 'video/quicktime',
+  '.mp3': 'audio/mpeg',
+  '.mp4': 'video/mp4',
+  '.ogg': 'audio/ogg',
+  '.pdf': 'application/pdf',
+  '.png': 'image/png',
+  '.ppt': 'application/vnd.ms-powerpoint',
+  '.pptx': 'application/vnd.openxmlformats-officedocument.presentationml.presentation',
+  '.rar': 'application/vnd.rar',
+  '.svg': 'image/svg+xml',
+  '.tar': 'application/x-tar',
+  '.txt': 'text/plain',
+  '.wav': 'audio/wav',
+  '.webm': 'video/webm',
+  '.webp': 'image/webp',
+  '.xls': 'application/vnd.ms-excel',
+  '.xlsx': 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',
+  '.xml': 'application/xml',
+  '.zip': 'application/zip'
+};
+
+interface ClipboardFilePayload {
+  data: string;
+  lastModified: number;
+  mime: string;
+  name: string;
+  path?: string;
+}
+
+function isSupportedClipboardFileFormat(format: string): boolean {
+  return FILE_CLIPBOARD_FORMATS.some(
+    (supportedFormat) => supportedFormat.toLowerCase() === format.toLowerCase()
+  );
+}
+
+function extractClipboardFilePaths(buffer: Buffer, format: string): string[] {
+  const textVariants = new Set<string>();
+  const utf8Text = buffer.toString('utf8').replace(/\0/g, '').trim();
+
+  if (utf8Text) {
+    textVariants.add(utf8Text);
+  }
+
+  if (format.toLowerCase() === 'filenamew') {
+    const utf16Text = buffer.toString('utf16le').replace(/\0/g, '\n').trim();
+
+    if (utf16Text) {
+      textVariants.add(utf16Text);
+    }
+  }
+
+  const filePaths = new Set<string>();
+
+  for (const text of textVariants) {
+    for (const filePath of parseClipboardFilePathText(text)) {
+      filePaths.add(filePath);
+    }
+  }
+
+  return [...filePaths];
+}
+
+function parseClipboardFilePathText(text: string): string[] {
+  return text
+    .split(/\r?\n/)
+    .map((line) => line.trim())
+    .filter(
+      (line) =>
+        !!line &&
+        !line.startsWith('#') &&
+        line.toLowerCase() !== 'copy' &&
+        line.toLowerCase() !== 'cut'
+    )
+    .flatMap((line) => {
+      if (line.startsWith('file://')) {
+        try {
+          return [fileURLToPath(line)];
+        } catch {
+          return [];
+        }
+      }
+
+      return path.isAbsolute(line) ? [line] : [];
+    });
+}
+
+function inferMimeType(filePath: string): string {
+  return MIME_TYPES_BY_EXTENSION[path.extname(filePath).toLowerCase()] ?? DEFAULT_MIME_TYPE;
+}
+
+async function readClipboardFiles(): Promise<ClipboardFilePayload[]> {
+  const formats = clipboard.availableFormats();
+  const filePaths = new Set<string>();
+
+  for (const format of formats) {
+    if (!isSupportedClipboardFileFormat(format)) {
+      continue;
+    }
+
+    try {
+      const buffer = clipboard.readBuffer(format);
+
+      for (const filePath of extractClipboardFilePaths(buffer, format)) {
+        filePaths.add(filePath);
+      }
+    } catch {
+      /* ignore unreadable clipboard formats */
+    }
+  }
+
+  const files: ClipboardFilePayload[] = [];
+
+  for (const filePath of filePaths) {
+    try {
+      const stats = await fsp.stat(filePath);
+
+      if (!stats.isFile()) {
+        continue;
+      }
+
+      const data = await fsp.readFile(filePath);
+
+      files.push({
+        data: data.toString('base64'),
+        lastModified: Math.round(stats.mtimeMs),
+        mime: inferMimeType(filePath),
+        name: path.basename(filePath),
+        path: filePath
+      });
+    } catch {
+      /* ignore files that are no longer readable */
+    }
+  }
+
+  return files;
+}
+
 export function setupSystemHandlers(): void {
   ipcMain.handle('open-external', async (_event, url: string) => {
     if (typeof url === 'string' && (url.startsWith('http://') || url.startsWith('https://'))) {
@@ -88,6 +251,10 @@ export function setupSystemHandlers(): void {
     return data.toString('base64');
   });
 
+  ipcMain.handle('read-clipboard-files', async () => {
+    return await readClipboardFiles();
+  });
+
   ipcMain.handle('write-file', async (_event, filePath: string, base64Data: string) => {
     const buffer = Buffer.from(base64Data, 'base64');
 
diff --git a/electron/preload.ts b/electron/preload.ts
index 4dfbff3..6e541ae 100644
--- a/electron/preload.ts
+++ b/electron/preload.ts
@@ -32,6 +32,14 @@ export interface LinuxScreenShareMonitorAudioEndedPayload {
   reason?: string;
 }
 
+export interface ClipboardFilePayload {
+  data: string;
+  lastModified: number;
+  mime: string;
+  name: string;
+  path?: string;
+}
+
 export interface ElectronAPI {
   minimizeWindow: () => void;
   maximizeWindow: () => void;
@@ -58,6 +66,7 @@ export interface ElectronAPI {
     restartRequired: boolean;
   }>;
   relaunchApp: () => Promise<boolean>;
+  readClipboardFiles: () => Promise<ClipboardFilePayload[]>;
   readFile: (filePath: string) => Promise<string>;
   writeFile: (filePath: string, data: string) => Promise<boolean>;
   saveFileAs: (defaultFileName: string, data: string) => Promise<{ saved: boolean; cancelled: boolean }>;
@@ -114,6 +123,7 @@ const electronAPI: ElectronAPI = {
   getDesktopSettings: () => ipcRenderer.invoke('get-desktop-settings'),
   setDesktopSettings: (patch) => ipcRenderer.invoke('set-desktop-settings', patch),
   relaunchApp: () => ipcRenderer.invoke('relaunch-app'),
+  readClipboardFiles: () => ipcRenderer.invoke('read-clipboard-files'),
   readFile: (filePath) => ipcRenderer.invoke('read-file', filePath),
   writeFile: (filePath, data) => ipcRenderer.invoke('write-file', filePath, data),
   saveFileAs: (defaultFileName, data) => ipcRenderer.invoke('save-file-as', defaultFileName, data),
diff --git a/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.html b/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.html
index 4244302..718e660 100644
--- a/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.html
+++ b/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.html
@@ -178,6 +178,7 @@
         (blur)="onInputBlur()"
         (keydown.enter)="onEnter($event)"
         (input)="onInputChange(); autoResizeTextarea()"
+        (paste)="onPaste($event)"
         (dragenter)="onDragEnter($event)"
         (dragover)="onDragOver($event)"
         (dragleave)="onDragLeave($event)"
diff --git a/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.ts b/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.ts
index f5d4756..5c09e49 100644
--- a/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.ts
+++ b/src/app/features/chat/chat-messages/components/message-composer/chat-message-composer.component.ts
@@ -25,6 +25,26 @@ import { TypingIndicatorComponent } from '../../../typing-indicator/typing-indic
 import { ChatMarkdownService } from '../../services/chat-markdown.service';
 import { ChatMessageComposerSubmitEvent } from '../../models/chat-messages.models';
 
+interface ClipboardFilePayload {
+  data: string;
+  lastModified: number;
+  mime: string;
+  name: string;
+  path?: string;
+}
+
+interface ClipboardElectronApi {
+  readClipboardFiles?: () => Promise<ClipboardFilePayload[]>;
+}
+
+type ClipboardWindow = Window & {
+  electronAPI?: ClipboardElectronApi;
+};
+
+type LocalFileWithPath = File & {
+  path?: string;
+};
+
 @Component({
   selector: 'app-chat-message-composer',
   standalone: true,
@@ -256,7 +276,7 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
   }
 
   onDragEnter(event: DragEvent): void {
-    if (!this.hasPotentialFilePayload(event))
+    if (!this.hasPotentialFilePayload(event.dataTransfer))
       return;
 
     event.preventDefault();
@@ -266,7 +286,7 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
   }
 
   onDragOver(event: DragEvent): void {
-    if (!this.hasPotentialFilePayload(event))
+    if (!this.hasPotentialFilePayload(event.dataTransfer))
       return;
 
     event.preventDefault();
@@ -296,17 +316,30 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
     event.preventDefault();
     event.stopPropagation();
     this.dragDepth = 0;
-    const droppedFiles = this.extractDroppedFiles(event);
+    const droppedFiles = this.extractFilesFromTransfer(event.dataTransfer);
 
     if (droppedFiles.length === 0) {
       this.dragActive.set(false);
       return;
     }
 
-    this.pendingFiles.push(...droppedFiles);
-    this.toolbarVisible.set(true);
+    this.addPendingFiles(droppedFiles);
     this.dragActive.set(false);
-    this.emitHeight();
+  }
+
+  async onPaste(event: ClipboardEvent): Promise<void> {
+    if (!this.hasPotentialFilePayload(event.clipboardData, false))
+      return;
+
+    event.preventDefault();
+    event.stopPropagation();
+
+    const pastedFiles = await this.extractPastedFiles(event);
+
+    if (pastedFiles.length === 0)
+      return;
+
+    this.addPendingFiles(pastedFiles);
   }
 
   autoResizeTextarea(): void {
@@ -375,8 +408,26 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
     }
   }
 
-  private hasPotentialFilePayload(event: DragEvent): boolean {
-    const dataTransfer = event.dataTransfer;
+  private addPendingFiles(files: File[]): void {
+    if (files.length === 0)
+      return;
+
+    const mergedFiles = this.mergeUniqueFiles(this.pendingFiles, files);
+
+    if (mergedFiles.length === this.pendingFiles.length)
+      return;
+
+    this.pendingFiles = mergedFiles;
+    this.toolbarVisible.set(true);
+    this.emitHeight();
+
+    requestAnimationFrame(() => this.messageInputRef?.nativeElement.focus());
+  }
+
+  private hasPotentialFilePayload(
+    dataTransfer: DataTransfer | null,
+    treatMissingTypesAsPotentialFile = true
+  ): boolean {
 
     if (!dataTransfer)
       return false;
@@ -397,14 +448,15 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
     const types = dataTransfer.types;
 
     if (!types || types.length === 0)
-      return true;
+      return treatMissingTypesAsPotentialFile;
 
     for (const type of types) {
       if (
         type === 'Files' ||
         type === 'application/x-moz-file' ||
         type === 'public.file-url' ||
-        type === 'text/uri-list'
+        type === 'text/uri-list' ||
+        type === 'x-special/gnome-copied-files'
       ) {
         return true;
       }
@@ -413,9 +465,9 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
     return false;
   }
 
-  private extractDroppedFiles(event: DragEvent): File[] {
-    const droppedFiles: File[] = [];
-    const items = event.dataTransfer?.items ?? null;
+  private extractFilesFromTransfer(dataTransfer: DataTransfer | null): File[] {
+    const extractedFiles: File[] = [];
+    const items = dataTransfer?.items ?? null;
 
     if (items && items.length) {
       for (const item of items) {
@@ -423,32 +475,128 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
           const file = item.getAsFile();
 
           if (file) {
-            droppedFiles.push(file);
+            this.pushUniqueFile(extractedFiles, file);
           }
         }
       }
     }
 
-    const files = event.dataTransfer?.files;
+    const files = dataTransfer?.files;
 
     if (!files?.length)
-      return droppedFiles;
+      return extractedFiles;
 
     for (const file of files) {
-      const exists = droppedFiles.some(
-        (existingFile) =>
-          existingFile.name === file.name &&
-          existingFile.size === file.size &&
-          existingFile.type === file.type &&
-          existingFile.lastModified === file.lastModified
-      );
+      this.pushUniqueFile(extractedFiles, file);
+    }
 
-      if (!exists) {
-        droppedFiles.push(file);
+    return extractedFiles;
+  }
+
+  private mergeUniqueFiles(existingFiles: File[], incomingFiles: File[]): File[] {
+    const mergedFiles = [...existingFiles];
+
+    for (const file of incomingFiles) {
+      this.pushUniqueFile(mergedFiles, file);
+    }
+
+    return mergedFiles;
+  }
+
+  private pushUniqueFile(target: File[], candidate: File): void {
+    const exists = target.some((file) => this.areFilesEquivalent(file, candidate));
+
+    if (!exists) {
+      target.push(candidate);
+    }
+  }
+
+  private areFilesEquivalent(left: File, right: File): boolean {
+    const leftPath = this.getLocalFilePath(left);
+    const rightPath = this.getLocalFilePath(right);
+
+    if (leftPath && rightPath) {
+      return leftPath === rightPath;
+    }
+
+    if (left.name !== right.name || left.size !== right.size) {
+      return false;
+    }
+
+    const leftType = left.type.trim();
+    const rightType = right.type.trim();
+
+    if (leftType && rightType && leftType !== rightType) {
+      return false;
+    }
+
+    const leftLastModified = Number.isFinite(left.lastModified) ? left.lastModified : 0;
+    const rightLastModified = Number.isFinite(right.lastModified) ? right.lastModified : 0;
+
+    if (!leftLastModified || !rightLastModified) {
+      return true;
+    }
+
+    return Math.abs(leftLastModified - rightLastModified) <= 1000;
+  }
+
+  private getLocalFilePath(file: File): string {
+    return ((file as LocalFileWithPath).path || '').trim();
+  }
+
+  private async extractPastedFiles(event: ClipboardEvent): Promise<File[]> {
+    const directFiles = this.extractFilesFromTransfer(event.clipboardData);
+
+    if (directFiles.length > 0)
+      return directFiles;
+
+    return await this.readFilesFromElectronClipboard();
+  }
+
+  private async readFilesFromElectronClipboard(): Promise<File[]> {
+    const electronApi = (window as ClipboardWindow).electronAPI;
+
+    if (!electronApi?.readClipboardFiles)
+      return [];
+
+    try {
+      const clipboardFiles = await electronApi.readClipboardFiles();
+
+      return clipboardFiles.map((clipboardFile) => this.createFileFromClipboardPayload(clipboardFile));
+    } catch {
+      return [];
+    }
+  }
+
+  private createFileFromClipboardPayload(payload: ClipboardFilePayload): File {
+    const file = new File([this.base64ToArrayBuffer(payload.data)], payload.name, {
+      lastModified: payload.lastModified,
+      type: payload.mime
+    });
+
+    if (payload.path) {
+      try {
+        Object.defineProperty(file, 'path', {
+          configurable: true,
+          value: payload.path
+        });
+      } catch {
+        (file as LocalFileWithPath).path = payload.path;
       }
     }
 
-    return droppedFiles;
+    return file;
+  }
+
+  private base64ToArrayBuffer(base64: string): ArrayBuffer {
+    const binaryString = atob(base64);
+    const bytes = new Uint8Array(binaryString.length);
+
+    for (let index = 0; index < binaryString.length; index++) {
+      bytes[index] = binaryString.charCodeAt(index);
+    }
+
+    return bytes.buffer;
   }
 
   private buildOutgoingMessageContent(raw: string): string {
diff --git a/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.html b/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.html
index 3ccc904..67f24ef 100644
--- a/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.html
+++ b/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.html
@@ -42,32 +42,36 @@
     </div>
 
     @if (isEditing()) {
-      <div class="mt-1 flex gap-2">
-        <input
-          type="text"
+      <div class="mt-1 flex items-start gap-2">
+        <textarea
+          #editTextareaRef
+          rows="1"
           [(ngModel)]="editContent"
-          (keydown.enter)="saveEdit()"
+          (keydown.enter)="onEditEnter($event)"
           (keydown.escape)="cancelEdit()"
-          class="flex-1 rounded border border-border bg-secondary px-3 py-1 text-foreground focus:outline-none focus:ring-2 focus:ring-primary"
-        />
-        <button
-          (click)="saveEdit()"
-          class="rounded p-1 text-primary hover:bg-primary/10"
-        >
-          <ng-icon
-            name="lucideCheck"
-            class="h-4 w-4"
-          />
-        </button>
-        <button
-          (click)="cancelEdit()"
-          class="rounded p-1 text-muted-foreground hover:bg-secondary"
-        >
-          <ng-icon
-            name="lucideX"
-            class="h-4 w-4"
-          />
-        </button>
+          (input)="autoResizeEditTextarea()"
+          class="edit-textarea flex-1 rounded border border-border bg-secondary px-3 py-2 text-foreground focus:outline-none focus:ring-2 focus:ring-primary"
+        ></textarea>
+        <div class="flex flex-col gap-2">
+          <button
+            (click)="saveEdit()"
+            class="rounded p-1 text-primary hover:bg-primary/10"
+          >
+            <ng-icon
+              name="lucideCheck"
+              class="h-4 w-4"
+            />
+          </button>
+          <button
+            (click)="cancelEdit()"
+            class="rounded p-1 text-muted-foreground hover:bg-secondary"
+          >
+            <ng-icon
+              name="lucideX"
+              class="h-4 w-4"
+            />
+          </button>
+        </div>
       </div>
     } @else {
       @if (msg.isDeleted) {
diff --git a/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.scss b/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.scss
index c246434..0dc88ea 100644
--- a/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.scss
+++ b/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.scss
@@ -179,3 +179,11 @@
     }
   }
 }
+
+.edit-textarea {
+  min-height: 42px;
+  max-height: 520px;
+  overflow-y: hidden;
+  resize: none;
+  transition: height 0.12s ease;
+}
diff --git a/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.ts b/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.ts
index 0de80ce..c744047 100644
--- a/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.ts
+++ b/src/app/features/chat/chat-messages/components/message-item/chat-message-item.component.ts
@@ -4,11 +4,13 @@ import { FormsModule } from '@angular/forms';
 import {
   Component,
   computed,
+  ElementRef,
   effect,
   inject,
   input,
   output,
-  signal
+  signal,
+  ViewChild
 } from '@angular/core';
 import { NgIcon, provideIcons } from '@ng-icons/core';
 import {
@@ -122,6 +124,8 @@ interface ChatMessageAttachmentViewModel extends Attachment {
   }
 })
 export class ChatMessageItemComponent {
+  @ViewChild('editTextareaRef') editTextareaRef?: ElementRef<HTMLTextAreaElement>;
+
   private readonly attachmentsSvc = inject(AttachmentService);
   private readonly klipy = inject(KlipyService);
   private readonly attachmentVersion = signal(this.attachmentsSvc.updated());
@@ -169,6 +173,28 @@ export class ChatMessageItemComponent {
   startEdit(): void {
     this.editContent = this.message().content;
     this.isEditing.set(true);
+
+    requestAnimationFrame(() => {
+      this.autoResizeEditTextarea();
+
+      const element = this.editTextareaRef?.nativeElement;
+
+      if (!element)
+        return;
+
+      element.focus();
+      element.setSelectionRange(element.value.length, element.value.length);
+    });
+  }
+
+  onEditEnter(event: Event): void {
+    const keyEvent = event as KeyboardEvent;
+
+    if (keyEvent.shiftKey)
+      return;
+
+    keyEvent.preventDefault();
+    this.saveEdit();
   }
 
   saveEdit(): void {
@@ -188,6 +214,17 @@ export class ChatMessageItemComponent {
     this.editContent = '';
   }
 
+  autoResizeEditTextarea(): void {
+    const element = this.editTextareaRef?.nativeElement;
+
+    if (!element)
+      return;
+
+    element.style.height = 'auto';
+    element.style.height = Math.min(element.scrollHeight, 520) + 'px';
+    element.style.overflowY = element.scrollHeight > 520 ? 'auto' : 'hidden';
+  }
+
   toggleEmojiPicker(): void {
     this.showEmojiPicker.update((current) => !current);
   }