✨ upload attachments and custom feedback

demo/main.tsx

@@ -15,6 +15,7 @@ import '@renderer/styles/app.css'
   removeAIListener: () => {},
   getProjectWordCount: () => Promise.resolve(0),
   saveOrder: () => Promise.resolve(),
+  pickAttachments: () => Promise.resolve([]),
   saveRevision: () => Promise.resolve(),
   listRevisions: () => Promise.resolve([]),
   loadRevision: () => Promise.resolve(''),

package-lock.json

@@ -21,6 +21,7 @@
         "codemirror": "^6.0.1",
         "dompurify": "^3.3.1",
         "marked": "^17.0.3",
+        "pdf-parse": "^2.4.5",
         "react": "^18.2.0",
         "react-dom": "^18.2.0",
         "zustand": "^4.5.0"
@@ -28,6 +29,7 @@
       "devDependencies": {
         "@electron-toolkit/tsconfig": "^1.0.1",
         "@types/node": "^20.0.0",
+        "@types/pdf-parse": "^1.1.5",
         "@types/react": "^18.2.0",
         "@types/react-dom": "^18.2.0",
         "@vitejs/plugin-react": "^4.2.0",
@@ -1520,6 +1522,190 @@
       "integrity": "sha512-l0h88YhZFyKdXIFNfSWpyjStDjGHwZ/U7iobcK1cQQD8sejsONdQtTVU+1wVN1PBw40PiiHB1vA5S7VTfQiP9g==",
       "license": "MIT"
     },
+    "node_modules/@napi-rs/canvas": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas/-/canvas-0.1.80.tgz",
+      "integrity": "sha512-DxuT1ClnIPts1kQx8FBmkk4BQDTfI5kIzywAaMjQSXfNnra5UFU9PwurXrl+Je3bJ6BGsp/zmshVVFbCmyI+ww==",
+      "license": "MIT",
+      "workspaces": [
+        "e2e/*"
+      ],
+      "engines": {
+        "node": ">= 10"
+      },
+      "optionalDependencies": {
+        "@napi-rs/canvas-android-arm64": "0.1.80",
+        "@napi-rs/canvas-darwin-arm64": "0.1.80",
+        "@napi-rs/canvas-darwin-x64": "0.1.80",
+        "@napi-rs/canvas-linux-arm-gnueabihf": "0.1.80",
+        "@napi-rs/canvas-linux-arm64-gnu": "0.1.80",
+        "@napi-rs/canvas-linux-arm64-musl": "0.1.80",
+        "@napi-rs/canvas-linux-riscv64-gnu": "0.1.80",
+        "@napi-rs/canvas-linux-x64-gnu": "0.1.80",
+        "@napi-rs/canvas-linux-x64-musl": "0.1.80",
+        "@napi-rs/canvas-win32-x64-msvc": "0.1.80"
+      }
+    },
+    "node_modules/@napi-rs/canvas-android-arm64": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-android-arm64/-/canvas-android-arm64-0.1.80.tgz",
+      "integrity": "sha512-sk7xhN/MoXeuExlggf91pNziBxLPVUqF2CAVnB57KLG/pz7+U5TKG8eXdc3pm0d7Od0WreB6ZKLj37sX9muGOQ==",
+      "cpu": [
+        "arm64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "android"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-darwin-arm64": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-darwin-arm64/-/canvas-darwin-arm64-0.1.80.tgz",
+      "integrity": "sha512-O64APRTXRUiAz0P8gErkfEr3lipLJgM6pjATwavZ22ebhjYl/SUbpgM0xcWPQBNMP1n29afAC/Us5PX1vg+JNQ==",
+      "cpu": [
+        "arm64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "darwin"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-darwin-x64": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-darwin-x64/-/canvas-darwin-x64-0.1.80.tgz",
+      "integrity": "sha512-FqqSU7qFce0Cp3pwnTjVkKjjOtxMqRe6lmINxpIZYaZNnVI0H5FtsaraZJ36SiTHNjZlUB69/HhxNDT1Aaa9vA==",
+      "cpu": [
+        "x64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "darwin"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-arm-gnueabihf": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-arm-gnueabihf/-/canvas-linux-arm-gnueabihf-0.1.80.tgz",
+      "integrity": "sha512-eyWz0ddBDQc7/JbAtY4OtZ5SpK8tR4JsCYEZjCE3dI8pqoWUC8oMwYSBGCYfsx2w47cQgQCgMVRVTFiiO38hHQ==",
+      "cpu": [
+        "arm"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-arm64-gnu": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-arm64-gnu/-/canvas-linux-arm64-gnu-0.1.80.tgz",
+      "integrity": "sha512-qwA63t8A86bnxhuA/GwOkK3jvb+XTQaTiVML0vAWoHyoZYTjNs7BzoOONDgTnNtr8/yHrq64XXzUoLqDzU+Uuw==",
+      "cpu": [
+        "arm64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-arm64-musl": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-arm64-musl/-/canvas-linux-arm64-musl-0.1.80.tgz",
+      "integrity": "sha512-1XbCOz/ymhj24lFaIXtWnwv/6eFHXDrjP0jYkc6iHQ9q8oXKzUX1Lc6bu+wuGiLhGh2GS/2JlfORC5ZcXimRcg==",
+      "cpu": [
+        "arm64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-riscv64-gnu": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-riscv64-gnu/-/canvas-linux-riscv64-gnu-0.1.80.tgz",
+      "integrity": "sha512-XTzR125w5ZMs0lJcxRlS1K3P5RaZ9RmUsPtd1uGt+EfDyYMu4c6SEROYsxyatbbu/2+lPe7MPHOO/0a0x7L/gw==",
+      "cpu": [
+        "riscv64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-x64-gnu": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-x64-gnu/-/canvas-linux-x64-gnu-0.1.80.tgz",
+      "integrity": "sha512-BeXAmhKg1kX3UCrJsYbdQd3hIMDH/K6HnP/pG2LuITaXhXBiNdh//TVVVVCBbJzVQaV5gK/4ZOCMrQW9mvuTqA==",
+      "cpu": [
+        "x64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-linux-x64-musl": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-linux-x64-musl/-/canvas-linux-x64-musl-0.1.80.tgz",
+      "integrity": "sha512-x0XvZWdHbkgdgucJsRxprX/4o4sEed7qo9rCQA9ugiS9qE2QvP0RIiEugtZhfLH3cyI+jIRFJHV4Fuz+1BHHMg==",
+      "cpu": [
+        "x64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@napi-rs/canvas-win32-x64-msvc": {
+      "version": "0.1.80",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-win32-x64-msvc/-/canvas-win32-x64-msvc-0.1.80.tgz",
+      "integrity": "sha512-Z8jPsM6df5V8B1HrCHB05+bDiCxjE9QA//3YrkKIdVDEwn5RKaqOxCJDRJkl48cJbylcrJbW4HxZbTte8juuPg==",
+      "cpu": [
+        "x64"
+      ],
+      "license": "MIT",
+      "optional": true,
+      "os": [
+        "win32"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
     "node_modules/@pkgjs/parseargs": {
       "version": "0.11.0",
       "resolved": "https://registry.npmjs.org/@pkgjs/parseargs/-/parseargs-0.11.0.tgz",
@@ -2056,6 +2242,16 @@
         "form-data": "^4.0.4"
       }
     },
+    "node_modules/@types/pdf-parse": {
+      "version": "1.1.5",
+      "resolved": "https://registry.npmjs.org/@types/pdf-parse/-/pdf-parse-1.1.5.tgz",
+      "integrity": "sha512-kBfrSXsloMnUJOKi25s3+hRmkycHfLK6A09eRGqF/N8BkQoPUmaCr+q8Cli5FnfohEz/rsv82zAiPz/LXtOGhA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": "*"
+      }
+    },
     "node_modules/@types/plist": {
       "version": "3.0.5",
       "resolved": "https://registry.npmjs.org/@types/plist/-/plist-3.0.5.tgz",
@@ -5107,6 +5303,38 @@
       "dev": true,
       "license": "ISC"
     },
+    "node_modules/pdf-parse": {
+      "version": "2.4.5",
+      "resolved": "https://registry.npmjs.org/pdf-parse/-/pdf-parse-2.4.5.tgz",
+      "integrity": "sha512-mHU89HGh7v+4u2ubfnevJ03lmPgQ5WU4CxAVmTSh/sxVTEDYd1er/dKS/A6vg77NX47KTEoihq8jZBLr8Cxuwg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@napi-rs/canvas": "0.1.80",
+        "pdfjs-dist": "5.4.296"
+      },
+      "bin": {
+        "pdf-parse": "bin/cli.mjs"
+      },
+      "engines": {
+        "node": ">=20.16.0 <21 || >=22.3.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/mehmet-kozan"
+      }
+    },
+    "node_modules/pdfjs-dist": {
+      "version": "5.4.296",
+      "resolved": "https://registry.npmjs.org/pdfjs-dist/-/pdfjs-dist-5.4.296.tgz",
+      "integrity": "sha512-DlOzet0HO7OEnmUmB6wWGJrrdvbyJKftI1bhMitK7O2N8W2gc757yyYBbINy9IDafXAV9wmKr9t7xsTaNKRG5Q==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=20.16.0 || >=22.3.0"
+      },
+      "optionalDependencies": {
+        "@napi-rs/canvas": "^0.1.80"
+      }
+    },
     "node_modules/pend": {
       "version": "1.2.0",
       "resolved": "https://registry.npmjs.org/pend/-/pend-1.2.0.tgz",

package.json

@@ -12,6 +12,7 @@
   "devDependencies": {
     "@electron-toolkit/tsconfig": "^1.0.1",
     "@types/node": "^20.0.0",
+    "@types/pdf-parse": "^1.1.5",
     "@types/react": "^18.2.0",
     "@types/react-dom": "^18.2.0",
     "@vitejs/plugin-react": "^4.2.0",
@@ -35,6 +36,7 @@
     "codemirror": "^6.0.1",
     "dompurify": "^3.3.1",
     "marked": "^17.0.3",
+    "pdf-parse": "^2.4.5",
     "react": "^18.2.0",
     "react-dom": "^18.2.0",
     "zustand": "^4.5.0"

src/main/aiService.ts

@@ -1,5 +1,5 @@
 import Anthropic from '@anthropic-ai/sdk'
-import type { AIPayload } from '../renderer/types/editor'
+import type { AIPayload, Attachment } from '../renderer/types/editor'
 
 let _client: Anthropic | null = null
 
@@ -89,7 +89,54 @@ SUGGESTION: [concrete direction]
 Name the single most important thing to fix in a revision of this chapter.`
   }
 
-  return `${chapterContext}\n\n${modeInstructions[payload.mode]}`
+  let prompt = `${chapterContext}\n\n${modeInstructions[payload.mode]}`
+
+  if (payload.attachments && payload.attachments.length > 0) {
+    const names = payload.attachments.map((a) => a.name).join(', ')
+    prompt += `\n\nThe user has attached the following reference file(s): ${names}.
+When suggesting edits based on the attached material, identify exact passages in the chapter and use this format for each suggestion:
+ISSUE: [category of improvement]
+PASSAGE: "[exact quoted text from the chapter]"
+PROBLEM: [brief explanation of why this needs changing]
+SUGGESTION: "[revised text]"`
+  }
+
+  return prompt
+}
+
+type UserContentBlock = Anthropic.ImageBlockParam | Anthropic.TextBlockParam
+
+function buildUserContent(
+  userMessage: string,
+  attachments: Attachment[] | undefined
+): string | UserContentBlock[] {
+  if (!attachments || attachments.length === 0) {
+    return userMessage
+  }
+
+  const content: UserContentBlock[] = []
+
+  for (const att of attachments) {
+    if (att.mimeType.startsWith('image/')) {
+      content.push({
+        type: 'image',
+        source: {
+          type: 'base64',
+          media_type: att.mimeType as 'image/jpeg' | 'image/png' | 'image/gif' | 'image/webp',
+          data: att.data
+        }
+      })
+    } else {
+      // Text or PDF — include as a fenced text block
+      content.push({
+        type: 'text',
+        text: `--- Attached: ${att.name} ---\n${att.data}\n--- End of ${att.name} ---`
+      })
+    }
+  }
+
+  content.push({ type: 'text', text: userMessage })
+  return content
 }
 
 export async function streamMessage(
@@ -98,9 +145,12 @@ export async function streamMessage(
 ): Promise<void> {
   const client = getClient()
 
-  const messages = [
+  const messages: Anthropic.MessageParam[] = [
     ...payload.conversationHistory.slice(-10),
-    { role: 'user' as const, content: payload.userMessage }
+    {
+      role: 'user' as const,
+      content: buildUserContent(payload.userMessage, payload.attachments)
+    }
   ]
 
   const stream = client.messages.stream({

src/main/ipcHandlers.ts

@@ -1,7 +1,9 @@
-import { ipcMain } from 'electron'
+import { ipcMain, dialog, BrowserWindow } from 'electron'
+import { readFileSync } from 'fs'
+import { extname, basename } from 'path'
 import { listDraftFiles, readMarkdownFile, writeMarkdownFile, getProjectWordCount, saveOrderFile, readSession, writeSession, saveRevision, listRevisions, loadRevision, deleteRevision } from './fileSystem'
 import { streamMessage } from './aiService'
-import type { AIPayload } from '../renderer/types/editor'
+import type { AIPayload, Attachment } from '../renderer/types/editor'
 
 export function registerIpcHandlers(): void {
   ipcMain.handle('fs:listFiles', async () => {
@@ -48,6 +50,48 @@ export function registerIpcHandlers(): void {
     await deleteRevision(filePath, revisionId)
   })
 
+  ipcMain.handle('fs:pickAttachments', async (event): Promise<Attachment[]> => {
+    const win = BrowserWindow.fromWebContents(event.sender)
+    const result = await dialog.showOpenDialog(win!, {
+      properties: ['openFile', 'multiSelections'],
+      filters: [
+        { name: 'Supported Files', extensions: ['jpg', 'jpeg', 'png', 'gif', 'webp', 'txt', 'md', 'pdf'] },
+        { name: 'Images', extensions: ['jpg', 'jpeg', 'png', 'gif', 'webp'] },
+        { name: 'Text Files', extensions: ['txt', 'md'] },
+        { name: 'PDF', extensions: ['pdf'] }
+      ]
+    })
+
+    if (result.canceled || result.filePaths.length === 0) return []
+
+    const attachments: Attachment[] = []
+    for (const filePath of result.filePaths) {
+      const name = basename(filePath)
+      const ext = extname(filePath).toLowerCase()
+
+      if (['.jpg', '.jpeg', '.png', '.gif', '.webp'].includes(ext)) {
+        const data = readFileSync(filePath).toString('base64')
+        const mimeType =
+          ext === '.jpg' || ext === '.jpeg' ? 'image/jpeg'
+          : ext === '.png' ? 'image/png'
+          : ext === '.gif' ? 'image/gif'
+          : 'image/webp'
+        attachments.push({ name, mimeType, data })
+      } else if (['.txt', '.md'].includes(ext)) {
+        const data = readFileSync(filePath, 'utf-8')
+        attachments.push({ name, mimeType: 'text/plain', data })
+      } else if (ext === '.pdf') {
+        // Dynamically require pdf-parse to avoid CJS/ESM issues at module load time
+        // eslint-disable-next-line @typescript-eslint/no-require-imports
+        const pdfParse = require('pdf-parse') as (buf: Buffer) => Promise<{ text: string }>
+        const buffer = readFileSync(filePath)
+        const parsed = await pdfParse(buffer)
+        attachments.push({ name, mimeType: 'application/pdf', data: parsed.text })
+      }
+    }
+    return attachments
+  })
+
   ipcMain.handle('ai:streamMessage', async (event, payload: AIPayload) => {
     try {
       await streamMessage(payload, (chunk: string) => {

src/preload/index.ts

@@ -1,5 +1,5 @@
 import { contextBridge, ipcRenderer } from 'electron'
-import type { FileNode, AIPayload, RevisionMeta } from '../renderer/types/editor'
+import type { FileNode, AIPayload, RevisionMeta, Attachment } from '../renderer/types/editor'
 
 contextBridge.exposeInMainWorld('api', {
   listFiles: (): Promise<FileNode[]> => ipcRenderer.invoke('fs:listFiles'),
@@ -39,6 +39,9 @@ contextBridge.exposeInMainWorld('api', {
     })
   },
 
+  pickAttachments: (): Promise<Attachment[]> =>
+    ipcRenderer.invoke('fs:pickAttachments'),
+
   removeAIListener: (): void => {
     ipcRenderer.removeAllListeners('ai:chunk')
     ipcRenderer.removeAllListeners('ai:done')

src/renderer/components/AIChat/Chat.css

@@ -278,13 +278,129 @@
 
 .chat-input-area {
   display: flex;
-  align-items: flex-end;
+  flex-direction: column;
-  gap: 8px;
+  gap: 6px;
   padding: 10px 12px;
   border-top: 1px solid var(--border);
   flex-shrink: 0;
 }
 
+/* ── Attachment chips bar (above the input row) ─── */
+.chat-attachments-bar {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 6px;
+}
+
+.chat-attachment-chip {
+  display: flex;
+  align-items: center;
+  gap: 5px;
+  background: var(--input-bg);
+  border: 1px solid var(--border);
+  border-radius: 20px;
+  padding: 3px 8px 3px 4px;
+  font-size: 11px;
+  color: var(--text-secondary);
+  max-width: 180px;
+}
+
+.chat-attachment-thumb {
+  width: 22px;
+  height: 22px;
+  object-fit: cover;
+  border-radius: 12px;
+  flex-shrink: 0;
+}
+
+.chat-attachment-icon {
+  font-size: 14px;
+  flex-shrink: 0;
+  line-height: 1;
+}
+
+.chat-attachment-name {
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+  flex: 1;
+  min-width: 0;
+}
+
+.chat-attachment-remove {
+  background: none;
+  border: none;
+  color: var(--text-muted);
+  cursor: pointer;
+  font-size: 14px;
+  line-height: 1;
+  padding: 0 1px;
+  flex-shrink: 0;
+  transition: color 0.12s;
+}
+
+.chat-attachment-remove:hover {
+  color: var(--text-primary);
+}
+
+/* ── Input row: paperclip + textarea + send ─── */
+.chat-input-row {
+  display: flex;
+  align-items: flex-end;
+  gap: 8px;
+}
+
+.chat-paperclip-btn {
+  background: none;
+  border: 1px solid var(--border);
+  border-radius: 6px;
+  color: var(--text-muted);
+  font-size: 18px;
+  width: 34px;
+  height: 34px;
+  cursor: pointer;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  flex-shrink: 0;
+  transition: color 0.15s, border-color 0.15s;
+  padding: 0;
+}
+
+.chat-paperclip-btn:hover:not(:disabled) {
+  color: var(--text-primary);
+  border-color: var(--text-muted);
+}
+
+.chat-paperclip-btn:disabled {
+  opacity: 0.35;
+  cursor: default;
+}
+
+/* ── Attachment chips shown inside past chat messages ─── */
+.chat-message-attachments {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 5px;
+  margin-bottom: 2px;
+}
+
+.chat-message-attachment-chip {
+  display: inline-flex;
+  align-items: center;
+  gap: 4px;
+  background: var(--input-bg);
+  border: 1px solid var(--border);
+  border-radius: 20px;
+  padding: 2px 8px;
+  font-size: 11px;
+  color: var(--text-muted);
+  max-width: 200px;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
+
 .chat-textarea {
   flex: 1;
   background: var(--input-bg);

src/renderer/components/AIChat/ChatInput.tsx

@@ -1,19 +1,28 @@
 import { useState, useRef, type KeyboardEvent } from 'react'
+import type { Attachment } from '../../types/editor'
 
 interface Props {
-  onSend: (text: string) => void
+  onSend: (text: string, attachments: Attachment[]) => void
   disabled: boolean
 }
 
+function attachmentIcon(mimeType: string): string {
+  if (mimeType.startsWith('image/')) return '🖼'
+  if (mimeType === 'application/pdf') return '📄'
+  return '📝'
+}
+
 export function ChatInput({ onSend, disabled }: Props): JSX.Element {
   const [value, setValue] = useState('')
+  const [attachments, setAttachments] = useState<Attachment[]>([])
   const textareaRef = useRef<HTMLTextAreaElement>(null)
 
   const submit = (): void => {
     const trimmed = value.trim()
-    if (!trimmed || disabled) return
+    if ((!trimmed && attachments.length === 0) || disabled) return
-    onSend(trimmed)
+    onSend(trimmed, attachments)
     setValue('')
+    setAttachments([])
     if (textareaRef.current) {
       textareaRef.current.style.height = 'auto'
     }
@@ -34,8 +43,63 @@ export function ChatInput({ onSend, disabled }: Props): JSX.Element {
     }
   }
 
+  const handleAttach = async (): Promise<void> => {
+    const picked = await window.api.pickAttachments()
+    if (picked.length === 0) return
+    // Deduplicate by name
+    setAttachments((prev) => {
+      const existingNames = new Set(prev.map((a) => a.name))
+      const fresh = picked.filter((a) => !existingNames.has(a.name))
+      return [...prev, ...fresh]
+    })
+  }
+
+  const removeAttachment = (name: string): void => {
+    setAttachments((prev) => prev.filter((a) => a.name !== name))
+  }
+
+  const canSend = !disabled && (value.trim().length > 0 || attachments.length > 0)
+
   return (
     <div className="chat-input-area">
+      {attachments.length > 0 && (
+        <div className="chat-attachments-bar">
+          {attachments.map((att) => (
+            <div key={att.name} className="chat-attachment-chip">
+              {att.mimeType.startsWith('image/') ? (
+                <img
+                  className="chat-attachment-thumb"
+                  src={`data:${att.mimeType};base64,${att.data}`}
+                  alt={att.name}
+                />
+              ) : (
+                <span className="chat-attachment-icon">{attachmentIcon(att.mimeType)}</span>
+              )}
+              <span className="chat-attachment-name" title={att.name}>
+                {att.name.length > 22 ? att.name.slice(0, 20) + '…' : att.name}
+              </span>
+              <button
+                className="chat-attachment-remove"
+                onClick={() => removeAttachment(att.name)}
+                aria-label={`Remove ${att.name}`}
+              >
+                ×
+              </button>
+            </div>
+          ))}
+        </div>
+      )}
+
+      <div className="chat-input-row">
+        <button
+          className="chat-paperclip-btn"
+          onClick={handleAttach}
+          disabled={disabled}
+          title="Attach file (image, text, PDF)"
+          aria-label="Attach file"
+        >
+          ⌁
+        </button>
         <textarea
           ref={textareaRef}
           className="chat-textarea"
@@ -50,11 +114,12 @@ export function ChatInput({ onSend, disabled }: Props): JSX.Element {
         <button
           className="chat-send-btn"
           onClick={submit}
-        disabled={disabled || !value.trim()}
+          disabled={!canSend}
           aria-label="Send"
         >
           ↑
         </button>
       </div>
+    </div>
   )
 }

src/renderer/components/AIChat/ChatMessageItem.tsx

@@ -5,6 +5,12 @@ import type { ChatMessage } from '../../types/editor'
 
 marked.setOptions({ breaks: true })
 
+function attachmentIcon(mimeType: string): string {
+  if (mimeType.startsWith('image/')) return '🖼'
+  if (mimeType === 'application/pdf') return '📄'
+  return '📝'
+}
+
 interface Props {
   message: ChatMessage
 }
@@ -21,6 +27,16 @@ export function ChatMessageItem({ message }: Props): JSX.Element {
       <div className="chat-message-label">
         {message.role === 'user' ? 'You' : 'Editor AI'}
       </div>
+      {message.attachments && message.attachments.length > 0 && (
+        <div className="chat-message-attachments">
+          {message.attachments.map((att) => (
+            <span key={att.name} className="chat-message-attachment-chip" title={att.name}>
+              {attachmentIcon(att.mimeType)}{' '}
+              {att.name.length > 24 ? att.name.slice(0, 22) + '…' : att.name}
+            </span>
+          ))}
+        </div>
+      )}
       <div className="chat-message-content">
         {html ? (
           <div

src/renderer/components/AIChat/ChatPanel.tsx

@@ -4,6 +4,7 @@ import { ChatMessageItem } from './ChatMessageItem'
 import { ChatInput } from './ChatInput'
 import { FeedbackPanel } from '../Feedback/FeedbackPanel'
 import { parseAnnotationsFromAIResponse } from '../../utils/annotationParser'
+import type { Attachment } from '../../types/editor'
 import './Chat.css'
 
 type TabId = 'chat' | 'feedback'
@@ -40,11 +41,11 @@ export function ChatPanel(): JSX.Element {
     prevAnnotationCountRef.current = curr
   }, [annotations])
 
-  const sendMessage = async (text: string): Promise<void> => {
+  const sendMessage = async (text: string, attachments: Attachment[]): Promise<void> => {
     if (!activeFilePath || isAILoading) return
 
     setAIError(null)
-    addUserMessage(text)
+    addUserMessage(text, attachments.map(({ name, mimeType }) => ({ name, mimeType })))
     startAssistantMessage()
     setAILoading(true)
 
@@ -58,7 +59,8 @@ export function ChatPanel(): JSX.Element {
           conversationHistory: chatHistory
             .slice(-10)
             .map((m) => ({ role: m.role, content: m.content })),
-          userMessage: text
+          userMessage: text,
+          attachments: attachments.length > 0 ? attachments : undefined
         },
         (chunk: string) => {
           appendToLastAssistantMessage(chunk)

src/renderer/store/editorStore.ts

@@ -1,5 +1,5 @@
 import { create } from 'zustand'
-import type { FileNode, ChatMessage, TextAnnotation, AnalysisMode, RevisionMeta } from '../types/editor'
+import type { FileNode, ChatMessage, TextAnnotation, AnalysisMode, RevisionMeta, AttachmentMeta } from '../types/editor'
 
 interface AnnotationFileState {
   mode: AnalysisMode
@@ -24,7 +24,7 @@ interface EditorState {
   chatHistory: ChatMessage[]
   isAILoading: boolean
   aiError: string | null
-  addUserMessage: (text: string) => void
+  addUserMessage: (text: string, attachments?: AttachmentMeta[]) => void
   startAssistantMessage: () => void
   appendToLastAssistantMessage: (chunk: string) => void
   setAILoading: (loading: boolean) => void
@@ -148,8 +148,8 @@ export const useEditorStore = create<EditorState>((set, get) => ({
   isAILoading: false,
   aiError: null,
 
-  addUserMessage: (text) => {
+  addUserMessage: (text, attachments?) => {
-    const msg: ChatMessage = { id: `user-${Date.now()}`, role: 'user', content: text }
+    const msg: ChatMessage = { id: `user-${Date.now()}`, role: 'user', content: text, attachments }
     set((s) => {
       const history = [...s.chatHistory, msg]
       const byFile = s.activeFilePath

src/renderer/types/editor.ts

@@ -5,10 +5,20 @@ export interface FileNode {
   children?: FileNode[]
 }
 
+export interface AttachmentMeta {
+  name: string
+  mimeType: string
+}
+
+export interface Attachment extends AttachmentMeta {
+  data: string // base64 for images, extracted text for text/PDF
+}
+
 export interface ChatMessage {
   id: string
   role: 'user' | 'assistant'
   content: string
+  attachments?: AttachmentMeta[] // metadata only — stored in history for display
 }
 
 export type AnnotationType = 'passive_voice' | 'consistency' | 'style' | 'critique'
@@ -33,6 +43,7 @@ export interface AIPayload {
   documentPath: string
   conversationHistory: Array<{ role: 'user' | 'assistant'; content: string }>
   userMessage: string
+  attachments?: Attachment[] // full data for current API call only
 }
 
 export interface RevisionMeta {

src/renderer/types/global.d.ts

@@ -1,4 +1,4 @@
-import type { FileNode, AIPayload, RevisionMeta } from './editor'
+import type { FileNode, AIPayload, RevisionMeta, Attachment } from './editor'
 
 declare global {
   interface Window {
@@ -13,6 +13,7 @@ declare global {
       removeAIListener: () => void
       getProjectWordCount: () => Promise<number>
       saveOrder: (order: Record<string, string[]>) => Promise<void>
+      pickAttachments: () => Promise<Attachment[]>
       saveRevision: (filePath: string, content: string) => Promise<void>
       listRevisions: (filePath: string) => Promise<RevisionMeta[]>
       loadRevision: (filePath: string, revisionId: string) => Promise<string>