diff --git a/app/(main)/chat/page.tsx b/app/(main)/chat/page.tsx
index 3d1e651..bda1634 100644
--- a/app/(main)/chat/page.tsx
+++ b/app/(main)/chat/page.tsx
@@ -16,8 +16,8 @@ import {
   ChatEmptyState,
   ChatInput,
   ChatMessageList,
+  VoiceInput,
 } from "@/app/components/chat";
-import VoiceInput from "@/app/components/chat/VoiceInput";
 import { useConfigs } from "@/app/hooks";
 import { useVoiceChat } from "@/app/hooks/useVoiceChat";
 import {
@@ -33,6 +33,7 @@ import {
   ChatMessage,
   LLMCallRequest,
   LLMInput,
+  LLMStructuredInput,
   SendInput,
 } from "@/app/lib/types/chat";
 import { SavedConfig } from "@/app/lib/types/configs";
@@ -45,7 +46,7 @@ function genId() {
 }
 
 function buildUserMessage(input: SendInput): ChatMessage {
-  return {
+  const base: ChatMessage = {
     id: genId(),
     role: "user",
     content:
@@ -56,18 +57,49 @@ function buildUserMessage(input: SendInput): ChatMessage {
     status: "complete",
     isVoice: input.kind === "audio",
   };
+  if (input.kind === "text" && input.attachments?.length) {
+    base.attachments = input.attachments.map((a) => ({
+      kind: a.kind,
+      name: a.name,
+      mimeType: a.mimeType,
+      previewUrl: `data:${a.mimeType};base64,${a.base64}`,
+    }));
+  }
+  return base;
 }
 
 function buildLLMInput(input: SendInput): LLMInput {
-  if (input.kind === "text") return input.text.trim();
-  return {
-    type: "audio",
-    content: {
-      format: "base64",
-      value: input.base64,
-      mime_type: input.mimeType,
-    },
-  };
+  if (input.kind === "audio") {
+    return {
+      type: "audio",
+      content: {
+        format: "base64",
+        value: input.base64,
+        mime_type: input.mimeType,
+      },
+    };
+  }
+  const text = input.text.trim();
+  const files = input.attachments ?? [];
+  if (files.length === 0) return text;
+  const items: LLMStructuredInput[] = [];
+  if (text) {
+    items.push({
+      type: "text",
+      content: { format: "text", value: text },
+    });
+  }
+  for (const a of files) {
+    items.push({
+      type: a.kind,
+      content: {
+        format: "base64",
+        value: a.base64,
+        mime_type: a.mimeType,
+      },
+    });
+  }
+  return items;
 }
 
 function buildPayload(
@@ -180,6 +212,11 @@ export default function ChatPage() {
     return () => abortRef.current?.abort();
   }, []);
 
+  useEffect(() => {
+    if (!configId || !configVersion) return;
+    void loadSingleVersion(configId, configVersion);
+  }, [configId, configVersion, loadSingleVersion]);
+
   const handleNewChat = useCallback(() => {
     abortRef.current?.abort();
     abortRef.current = null;
@@ -201,7 +238,13 @@ export default function ChatPage() {
 
   const sendMessage = useCallback(
     async (input: SendInput): Promise<string | null> => {
-      if (input.kind === "text" && !input.text.trim()) return null;
+      if (
+        input.kind === "text" &&
+        !input.text.trim() &&
+        !input.attachments?.length
+      ) {
+        return null;
+      }
 
       if (!isAuthenticated) {
         setShowLoginModal(true);
@@ -459,7 +502,10 @@ export default function ChatPage() {
             <ChatInput
               value={draft}
               onChange={setDraft}
-              onSend={() => sendMessage({ kind: "text", text: draft })}
+              onSend={(attachments) =>
+                sendMessage({ kind: "text", text: draft, attachments })
+              }
+              onAttachmentError={(msg) => toast.error(msg)}
               isPending={isPending}
               onStartVoice={handleStartVoice}
               voiceConfigReady={hasConfig ? voiceConfigReady : undefined}
diff --git a/app/components/chat/AttachmentChip.tsx b/app/components/chat/AttachmentChip.tsx
new file mode 100644
index 0000000..e07ca8e
--- /dev/null
+++ b/app/components/chat/AttachmentChip.tsx
@@ -0,0 +1,88 @@
+"use client";
+
+import { MouseEvent } from "react";
+import { CloseIcon, DocumentFileIcon } from "@/app/components/icons";
+
+export interface AttachmentChipFile {
+  id: string;
+  kind: "image" | "pdf";
+  name: string;
+  mimeType: string;
+  previewUrl: string;
+}
+
+interface AttachmentChipProps {
+  file: AttachmentChipFile;
+  onRemove: () => void;
+  onPreview: () => void;
+}
+
+export default function AttachmentChip({
+  file,
+  onRemove,
+  onPreview,
+}: AttachmentChipProps) {
+  const handleRemove = (e: MouseEvent) => {
+    e.stopPropagation();
+    onRemove();
+  };
+  if (file.kind === "image") {
+    return (
+      <div className="relative group">
+        <button
+          type="button"
+          onClick={onPreview}
+          aria-label={`Preview ${file.name}`}
+          title={`Preview ${file.name}`}
+          className="block rounded-lg overflow-hidden cursor-pointer focus:outline-none focus:ring-2 focus:ring-accent-primary"
+        >
+          <img
+            src={file.previewUrl}
+            alt={file.name}
+            className="w-16 h-16 rounded-lg object-cover bg-bg-primary shadow-[0_2px_6px_rgba(0,0,0,0.08),0_1px_2px_rgba(0,0,0,0.05)]"
+          />
+        </button>
+        <button
+          type="button"
+          onClick={handleRemove}
+          aria-label={`Remove ${file.name}`}
+          className="absolute -top-1.5 -right-1.5 w-5 h-5 rounded-full bg-text-primary text-white flex items-center justify-center shadow-[0_1px_3px_rgba(0,0,0,0.2)] hover:bg-neutral-800 transition-colors cursor-pointer"
+        >
+          <CloseIcon className="w-3 h-3" />
+        </button>
+      </div>
+    );
+  }
+  return (
+    <div className="relative">
+      <button
+        type="button"
+        onClick={onPreview}
+        aria-label={`Preview ${file.name}`}
+        title={`Preview ${file.name}`}
+        className="inline-flex items-center gap-2 pr-7 pl-2 py-1.5 rounded-lg bg-bg-primary shadow-[0_2px_6px_rgba(0,0,0,0.08),0_1px_2px_rgba(0,0,0,0.05)] hover:bg-bg-secondary transition-colors cursor-pointer text-left"
+      >
+        <span className="inline-flex items-center justify-center w-8 h-8 rounded-md bg-accent-primary text-white shrink-0">
+          <DocumentFileIcon className="w-4 h-4" />
+        </span>
+        <span className="flex flex-col min-w-0 max-w-[180px]">
+          <span
+            className="text-sm font-medium text-text-primary truncate"
+            title={file.name}
+          >
+            {file.name}
+          </span>
+          <span className="text-[11px] text-text-secondary">PDF</span>
+        </span>
+      </button>
+      <button
+        type="button"
+        onClick={handleRemove}
+        aria-label={`Remove ${file.name}`}
+        className="absolute -top-1.5 -right-1.5 w-5 h-5 rounded-full bg-text-primary text-white flex items-center justify-center shadow-[0_1px_3px_rgba(0,0,0,0.2)] hover:bg-neutral-800 transition-colors cursor-pointer"
+      >
+        <CloseIcon className="w-3 h-3" />
+      </button>
+    </div>
+  );
+}
diff --git a/app/components/chat/AttachmentPreviewModal.tsx b/app/components/chat/AttachmentPreviewModal.tsx
new file mode 100644
index 0000000..3559854
--- /dev/null
+++ b/app/components/chat/AttachmentPreviewModal.tsx
@@ -0,0 +1,53 @@
+"use client";
+
+import { Modal } from "@/app/components/ui";
+
+export interface PreviewableAttachment {
+  kind: "image" | "pdf";
+  name: string;
+  mimeType: string;
+  previewUrl?: string;
+}
+
+interface AttachmentPreviewModalProps {
+  attachment: PreviewableAttachment | null;
+  onClose: () => void;
+}
+
+export default function AttachmentPreviewModal({
+  attachment,
+  onClose,
+}: AttachmentPreviewModalProps) {
+  const open = !!attachment;
+  return (
+    <Modal
+      open={open}
+      onClose={onClose}
+      title={attachment?.name ?? "Preview"}
+      maxWidth="max-w-4xl"
+      maxHeight="max-h-[90vh]"
+    >
+      <div className="px-6 pb-6 h-full">
+        {attachment?.kind === "image" && attachment.previewUrl ? (
+          <div className="flex items-center justify-center h-full">
+            <img
+              src={attachment.previewUrl}
+              alt={attachment.name}
+              className="max-w-full max-h-[75vh] object-contain rounded-lg"
+            />
+          </div>
+        ) : attachment?.previewUrl ? (
+          <iframe
+            src={attachment.previewUrl}
+            title={attachment.name}
+            className="w-full h-[75vh] rounded-lg border border-border"
+          />
+        ) : (
+          <p className="text-sm text-text-secondary text-center py-12">
+            Preview is not available for this attachment.
+          </p>
+        )}
+      </div>
+    </Modal>
+  );
+}
diff --git a/app/components/chat/ChatInput.tsx b/app/components/chat/ChatInput.tsx
index 815fb85..80a329c 100644
--- a/app/components/chat/ChatInput.tsx
+++ b/app/components/chat/ChatInput.tsx
@@ -1,16 +1,31 @@
 /**
- * ChatInput - Auto-growing textarea with a send button.
+ * ChatInput - Auto-growing textarea with a send button, attachments
+ * (image / pdf, max 2) and drag-and-drop.
  */
 
 "use client";
 
-import { KeyboardEvent, ReactNode, useEffect, useRef } from "react";
-import { InfoIcon, MicIcon, SendIcon } from "@/app/components/icons";
+import {
+  ChangeEvent,
+  DragEvent,
+  KeyboardEvent,
+  ReactNode,
+  useEffect,
+  useRef,
+  useState,
+} from "react";
+import { InfoIcon, MicIcon, PlusIcon, SendIcon } from "@/app/components/icons";
+import { SendAttachment } from "@/app/lib/types/chat";
+import {
+  AttachmentChip,
+  AttachmentPreviewModal,
+  PreviewableAttachment,
+} from "@/app/components/chat";
 
 interface ChatInputProps {
   value: string;
   onChange: (next: string) => void;
-  onSend: () => void;
+  onSend: (attachments?: SendAttachment[]) => void;
   disabled?: boolean;
   isPending?: boolean;
   placeholder?: string;
@@ -19,9 +34,47 @@ interface ChatInputProps {
   onStartVoice?: () => void;
   voiceConfigReady?: boolean;
   textConfigReady?: boolean;
+  onAttachmentError?: (message: string) => void;
 }
 
 const MAX_HEIGHT_PX = 200;
+const MAX_FILES = 2;
+const ALLOWED_IMAGE_TYPES = [
+  "image/jpeg",
+  "image/png",
+  "image/gif",
+  "image/webp",
+];
+const ALLOWED_PDF_TYPE = "application/pdf";
+const ACCEPT_ATTR = [...ALLOWED_IMAGE_TYPES, ALLOWED_PDF_TYPE].join(",");
+
+interface AttachedFile {
+  id: string;
+  kind: "image" | "pdf";
+  name: string;
+  mimeType: string;
+  base64: string;
+  previewUrl: string;
+}
+
+function classifyMime(mime: string): "image" | "pdf" | null {
+  if (ALLOWED_IMAGE_TYPES.includes(mime)) return "image";
+  if (mime === ALLOWED_PDF_TYPE) return "pdf";
+  return null;
+}
+
+function readFileAsBase64(file: File): Promise<string> {
+  return new Promise((resolve, reject) => {
+    const reader = new FileReader();
+    reader.onload = () => {
+      const result = reader.result as string;
+      const comma = result.indexOf(",");
+      resolve(comma >= 0 ? result.slice(comma + 1) : result);
+    };
+    reader.onerror = () => reject(reader.error);
+    reader.readAsDataURL(file);
+  });
+}
 
 export default function ChatInput({
   value,
@@ -35,8 +88,14 @@ export default function ChatInput({
   onStartVoice,
   voiceConfigReady,
   textConfigReady,
+  onAttachmentError,
 }: ChatInputProps) {
   const ref = useRef<HTMLTextAreaElement>(null);
+  const fileInputRef = useRef<HTMLInputElement>(null);
+  const [attachments, setAttachments] = useState<AttachedFile[]>([]);
+  const [isDragging, setIsDragging] = useState(false);
+  const [preview, setPreview] = useState<PreviewableAttachment | null>(null);
+  const dragCounterRef = useRef(0);
 
   useEffect(() => {
     const el = ref.current;
@@ -45,21 +104,151 @@ export default function ChatInput({
     el.style.height = `${Math.min(el.scrollHeight, MAX_HEIGHT_PX)}px`;
   }, [value]);
 
+  const reportError = (msg: string) => {
+    if (onAttachmentError) onAttachmentError(msg);
+  };
+
+  const ingestFiles = async (incoming: FileList | File[]) => {
+    const list = Array.from(incoming);
+    if (list.length === 0) return;
+    const rejected: string[] = [];
+    const accepted: File[] = [];
+    for (const file of list) {
+      const kind = classifyMime(file.type);
+      if (!kind) {
+        rejected.push(file.name);
+        continue;
+      }
+      accepted.push(file);
+    }
+    if (rejected.length) {
+      reportError(
+        `Unsupported file type: ${rejected.join(", ")}. Allowed: JPG, PNG, GIF, WebP, PDF.`,
+      );
+    }
+    const room = MAX_FILES - attachments.length;
+    const toAdd = accepted.slice(0, Math.max(0, room));
+    if (accepted.length > toAdd.length) {
+      reportError(`You can attach up to ${MAX_FILES} files at once.`);
+    }
+
+    const added: AttachedFile[] = await Promise.all(
+      toAdd.map(async (file) => {
+        const base64 = await readFileAsBase64(file);
+        const kind = classifyMime(file.type) as "image" | "pdf";
+        return {
+          id: `${Date.now()}-${Math.random().toString(36).slice(2, 9)}`,
+          kind,
+          name: file.name,
+          mimeType: file.type,
+          base64,
+          previewUrl: `data:${file.type};base64,${base64}`,
+        };
+      }),
+    );
+    if (added.length === 0) return;
+    setAttachments((prev) => [...prev, ...added].slice(0, MAX_FILES));
+  };
+
+  const handleFileInputChange = async (e: ChangeEvent<HTMLInputElement>) => {
+    if (e.target.files) await ingestFiles(e.target.files);
+    e.target.value = "";
+  };
+
+  const handleDragEnter = (e: DragEvent<HTMLDivElement>) => {
+    e.preventDefault();
+    e.stopPropagation();
+    if (!e.dataTransfer?.types.includes("Files")) return;
+    if (attachments.length >= MAX_FILES) return;
+    dragCounterRef.current += 1;
+    setIsDragging(true);
+  };
+  const handleDragLeave = (e: DragEvent<HTMLDivElement>) => {
+    e.preventDefault();
+    e.stopPropagation();
+    dragCounterRef.current = Math.max(0, dragCounterRef.current - 1);
+    if (dragCounterRef.current === 0) setIsDragging(false);
+  };
+  const handleDragOver = (e: DragEvent<HTMLDivElement>) => {
+    e.preventDefault();
+    e.stopPropagation();
+    if (e.dataTransfer) e.dataTransfer.dropEffect = "copy";
+  };
+  const handleDrop = async (e: DragEvent<HTMLDivElement>) => {
+    e.preventDefault();
+    e.stopPropagation();
+    dragCounterRef.current = 0;
+    setIsDragging(false);
+    if (attachments.length >= MAX_FILES) {
+      reportError(`You can attach up to ${MAX_FILES} files at once.`);
+      return;
+    }
+    if (e.dataTransfer?.files) await ingestFiles(e.dataTransfer.files);
+  };
+
+  const removeAttachment = (id: string) => {
+    setAttachments((prev) => prev.filter((a) => a.id !== id));
+  };
+
+  const handleSend = () => {
+    if (!canSend) return;
+    const payload: SendAttachment[] | undefined = attachments.length
+      ? attachments.map((a) => ({
+          kind: a.kind,
+          name: a.name,
+          mimeType: a.mimeType,
+          base64: a.base64,
+        }))
+      : undefined;
+    onSend(payload);
+    setAttachments([]);
+  };
+
   const handleKeyDown = (e: KeyboardEvent<HTMLTextAreaElement>) => {
     if (e.key === "Enter" && !e.shiftKey) {
       e.preventDefault();
-      if (!disabled && !isPending && value.trim()) {
-        onSend();
-      }
+      handleSend();
     }
   };
 
-  const canSend = !disabled && !isPending && value.trim().length > 0;
+  const hasContent = value.trim().length > 0 || attachments.length > 0;
+  const canSend = !disabled && !isPending && hasContent;
+  const canAttachMore = attachments.length < MAX_FILES;
 
   return (
     <div className="px-4 sm:px-6 pb-6 pt-2 bg-bg-primary">
       <div className="max-w-3xl mx-auto">
-        <div className="rounded-3xl border border-border bg-bg-primary shadow-[0_2px_12px_rgba(0,0,0,0.04)] transition-colors">
+        <div
+          className={`relative rounded-3xl border bg-bg-primary shadow-[0_2px_12px_rgba(0,0,0,0.04)] transition-colors ${
+            isDragging
+              ? "border-accent-primary bg-accent-primary/5"
+              : "border-border"
+          }`}
+          onDragEnter={handleDragEnter}
+          onDragOver={handleDragOver}
+          onDragLeave={handleDragLeave}
+          onDrop={handleDrop}
+        >
+          {attachments.length > 0 && (
+            <div className="flex flex-wrap items-start gap-2 px-3 pt-3">
+              {attachments.map((a) => (
+                <AttachmentChip
+                  key={a.id}
+                  file={a}
+                  onRemove={() => removeAttachment(a.id)}
+                  onPreview={() =>
+                    setPreview({
+                      kind: a.kind,
+                      name: a.name,
+                      mimeType: a.mimeType,
+                      previewUrl: a.previewUrl,
+                    })
+                  }
+                />
+              ))}
+            </div>
+          )}
+
           <textarea
             ref={ref}
             value={value}
@@ -72,6 +261,32 @@ export default function ChatInput({
             style={{ maxHeight: MAX_HEIGHT_PX }}
           />
           <div className="flex items-center gap-2 px-3 pb-2 pt-1">
+            <button
+              type="button"
+              onClick={() => fileInputRef.current?.click()}
+              disabled={disabled || isPending || !canAttachMore}
+              aria-label="Attach files"
+              title={
+                canAttachMore
+                  ? "Attach an image or PDF (max 2)"
+                  : `You've attached the maximum ${MAX_FILES} files`
+              }
+              className={`shrink-0 w-9 h-9 rounded-full border border-border bg-bg-primary flex items-center justify-center transition-colors ${
+                canAttachMore && !disabled && !isPending
+                  ? "text-text-secondary hover:text-accent-primary hover:border-accent-primary hover:bg-accent-primary/5 cursor-pointer"
+                  : "text-text-secondary/40 opacity-60 cursor-not-allowed"
+              }`}
+            >
+              <PlusIcon className="w-4 h-4" />
+            </button>
+            <input
+              ref={fileInputRef}
+              type="file"
+              accept={ACCEPT_ATTR}
+              multiple
+              hidden
+              onChange={handleFileInputChange}
+            />
             <div className="flex-1" />
             {trailingAccessory && (
               <div className="flex items-center gap-2 min-w-0">
@@ -100,7 +315,7 @@ export default function ChatInput({
             )}
             <button
               type="button"
-              onClick={onSend}
+              onClick={handleSend}
               disabled={!canSend}
               aria-label="Send message"
               className={`shrink-0 w-9 h-9 rounded-full flex items-center justify-center transition-colors ${
@@ -112,6 +327,14 @@ export default function ChatInput({
               <SendIcon className="w-4 h-4" />
             </button>
           </div>
+
+          {isDragging && (
+            <div className="pointer-events-none absolute inset-0 rounded-3xl border-2 border-dashed border-accent-primary bg-accent-primary/10 flex items-center justify-center">
+              <span className="text-sm font-medium text-accent-primary">
+                Drop image or PDF to attach
+              </span>
+            </div>
+          )}
         </div>
         {textConfigReady === false ? (
           <div className="mt-2 flex items-start justify-center gap-1.5 text-[11px] text-status-warning-text">
@@ -138,6 +361,10 @@ export default function ChatInput({
           </p>
         )}
       </div>
+      <AttachmentPreviewModal
+        attachment={preview}
+        onClose={() => setPreview(null)}
+      />
     </div>
   );
 }
diff --git a/app/components/chat/ChatMessage.tsx b/app/components/chat/ChatMessage.tsx
index 4f59fa2..d198543 100644
--- a/app/components/chat/ChatMessage.tsx
+++ b/app/components/chat/ChatMessage.tsx
@@ -5,41 +5,25 @@
 "use client";
 
 import { useState } from "react";
-import { ChatMessage as ChatMessageType } from "@/app/lib/types/chat";
+import {
+  ChatAttachment,
+  ChatMessage as ChatMessageType,
+} from "@/app/lib/types/chat";
 import {
   ChatIcon,
   CheckLineIcon,
   CopyIcon,
+  DocumentFileIcon,
   MicIcon,
   SpeakerIcon,
 } from "@/app/components/icons";
+import { AttachmentPreviewModal, MarkdownContent } from "@/app/components/chat";
 import { useTextToSpeech } from "@/app/hooks/useTextToSpeech";
 
 interface ChatMessageProps {
   message: ChatMessageType;
 }
 
-interface WordSegment {
-  text: string;
-  start: number;
-  isWord: boolean;
-}
-
-function tokenizeWords(text: string): WordSegment[] {
-  const segments: WordSegment[] = [];
-  const re = /(\S+|\s+)/g;
-  let match: RegExpExecArray | null;
-  while ((match = re.exec(text)) !== null) {
-    const value = match[0];
-    segments.push({
-      text: value,
-      start: match.index,
-      isWord: !/^\s+$/.test(value),
-    });
-  }
-  return segments;
-}
-
 function VoiceMessageBody() {
   return (
     <span className="inline-flex items-center gap-2.5 align-middle">
@@ -74,44 +58,17 @@ function ThinkingDots() {
   );
 }
 
-/**
- * Renders the assistant text with optional karaoke highlight.
- */
 function AssistantBody({
   text,
-  charIndex,
   baseClass,
   trailing,
 }: {
   text: string;
-  charIndex: number | null;
   baseClass: string;
   trailing?: React.ReactNode;
 }) {
-  const segments = tokenizeWords(text);
-  const isKaraoke = typeof charIndex === "number";
   return (
-    <div
-      className={`${baseClass} whitespace-pre-wrap wrap-break-word transition-colors`}
-    >
-      {segments.map((seg, i) => {
-        if (!seg.isWord) return <span key={i}>{seg.text}</span>;
-        const isRead = !isKaraoke || seg.start <= charIndex;
-        return (
-          <span
-            key={i}
-            className={
-              isRead
-                ? "text-text-primary transition-colors duration-150"
-                : "text-text-secondary/60 transition-colors duration-150"
-            }
-          >
-            {seg.text}
-          </span>
-        );
-      })}
-      {trailing}
-    </div>
+    <MarkdownContent text={text} className={baseClass} trailing={trailing} />
   );
 }
 
@@ -162,7 +119,7 @@ function AssistantMessage({ message }: { message: ChatMessageType }) {
     isError ? "text-status-error" : "text-text-primary"
   }`;
 
-  const { isSpeaking, charIndex, speak, stop } = useTextToSpeech();
+  const { isSpeaking, speak, stop } = useTextToSpeech();
   const [copied, setCopied] = useState(false);
 
   const handleSpeak = () => {
@@ -200,7 +157,6 @@ function AssistantMessage({ message }: { message: ChatMessageType }) {
         ) : (
           <AssistantBody
             text={message.content}
-            charIndex={isSpeaking ? charIndex : null}
             baseClass={baseClass}
             trailing={
               isPending && message.content ? (
@@ -244,30 +200,94 @@ function AssistantMessage({ message }: { message: ChatMessageType }) {
   );
 }
 
+function UserAttachments({ items }: { items: ChatAttachment[] }) {
+  const [preview, setPreview] = useState<ChatAttachment | null>(null);
+  const cardClass =
+    "flex-1 min-w-0 basis-[180px] max-w-xs rounded-xl bg-bg-primary shadow-[0_2px_6px_rgba(0,0,0,0.08),0_1px_2px_rgba(0,0,0,0.05)] overflow-hidden cursor-pointer hover:shadow-[0_4px_12px_rgba(0,0,0,0.12),0_2px_4px_rgba(0,0,0,0.06)] transition-shadow";
+  return (
+    <>
+      <div className="flex flex-wrap justify-end gap-2 mb-2 max-w-full">
+        {items.map((a, i) =>
+          a.kind === "image" && a.previewUrl ? (
+            <button
+              key={i}
+              type="button"
+              onClick={() => setPreview(a)}
+              title={a.name}
+              aria-label={`Preview ${a.name}`}
+              className={`${cardClass} bg-bg-secondary text-left`}
+            >
+              <img
+                src={a.previewUrl}
+                alt={a.name}
+                className="block w-full max-h-56 object-contain"
+              />
+            </button>
+          ) : (
+            <button
+              key={i}
+              type="button"
+              onClick={() => setPreview(a)}
+              className={`${cardClass} flex items-center gap-2.5 px-3 py-2.5 hover:bg-bg-secondary text-left`}
+              title={a.name}
+              aria-label={`Preview ${a.name}`}
+            >
+              <span className="inline-flex items-center justify-center w-9 h-9 rounded-md bg-accent-primary text-white shrink-0">
+                <DocumentFileIcon className="w-4 h-4" />
+              </span>
+              <span className="flex flex-col min-w-0 flex-1">
+                <span className="text-[13px] font-medium text-text-primary truncate">
+                  {a.name}
+                </span>
+                <span className="text-[11px] text-text-secondary">
+                  {a.kind === "pdf" ? "PDF" : a.mimeType}
+                </span>
+              </span>
+            </button>
+          ),
+        )}
+      </div>
+      <AttachmentPreviewModal
+        attachment={preview}
+        onClose={() => setPreview(null)}
+      />
+    </>
+  );
+}
+
 export default function ChatMessage({ message }: ChatMessageProps) {
   const isUser = message.role === "user";
 
   if (isUser) {
     const isVoiceWithoutTranscript =
       !!message.isVoice && !message.content.trim();
+    const attachments = message.attachments ?? [];
+    const hasAttachments = attachments.length > 0;
     return (
       <div className="flex justify-end px-4 sm:px-6">
-        <div className="max-w-[85%] sm:max-w-[75%] rounded-2xl bg-neutral-100 px-4 py-2.5 text-[15px] leading-relaxed text-text-primary whitespace-pre-wrap wrap-break-word">
-          {isVoiceWithoutTranscript ? (
-            <VoiceMessageBody />
-          ) : (
-            <>
-              {message.isVoice && (
-                <span
-                  className="mr-2 inline-flex items-center justify-center w-5 h-5 rounded-full bg-accent-primary/10 text-accent-primary align-text-bottom"
-                  title="Voice message"
-                  aria-label="Voice message"
-                >
-                  <MicIcon className="w-3 h-3" />
-                </span>
+        <div className="max-w-[85%] sm:max-w-[75%] flex flex-col items-end gap-1">
+          {hasAttachments && <UserAttachments items={attachments} />}
+          {(isVoiceWithoutTranscript ||
+            message.content.trim() ||
+            !hasAttachments) && (
+            <div className="rounded-2xl bg-neutral-100 px-4 py-2.5 text-[15px] leading-relaxed text-text-primary whitespace-pre-wrap wrap-break-word">
+              {isVoiceWithoutTranscript ? (
+                <VoiceMessageBody />
+              ) : (
+                <>
+                  {message.isVoice && (
+                    <span
+                      className="mr-2 inline-flex items-center justify-center w-5 h-5 rounded-full bg-accent-primary/10 text-accent-primary align-text-bottom"
+                      title="Voice message"
+                      aria-label="Voice message"
+                    >
+                      <MicIcon className="w-3 h-3" />
+                    </span>
+                  )}
+                  {message.content}
+                </>
               )}
-              {message.content}
-            </>
+            </div>
           )}
         </div>
       </div>
diff --git a/app/components/chat/ChatMessageList.tsx b/app/components/chat/ChatMessageList.tsx
index a3cba56..7a529c3 100644
--- a/app/components/chat/ChatMessageList.tsx
+++ b/app/components/chat/ChatMessageList.tsx
@@ -6,7 +6,7 @@
 
 import { useEffect, useRef } from "react";
 import { ChatMessage as ChatMessageType } from "@/app/lib/types/chat";
-import ChatMessage from "@/app/components/chat/ChatMessage";
+import { ChatMessage } from "@/app/components/chat";
 
 interface ChatMessageListProps {
   messages: ChatMessageType[];
diff --git a/app/components/chat/MarkdownContent.tsx b/app/components/chat/MarkdownContent.tsx
new file mode 100644
index 0000000..4416723
--- /dev/null
+++ b/app/components/chat/MarkdownContent.tsx
@@ -0,0 +1,165 @@
+"use client";
+
+import { ReactNode, useState } from "react";
+import ReactMarkdown, { Components } from "react-markdown";
+import remarkGfm from "remark-gfm";
+import rehypeHighlight from "rehype-highlight";
+import { CheckLineIcon, CopyIcon } from "@/app/components/icons";
+
+interface MarkdownContentProps {
+  text: string;
+  className?: string;
+  trailing?: ReactNode;
+}
+
+function CodeBlock({
+  className,
+  children,
+}: {
+  className?: string;
+  children: ReactNode;
+}) {
+  const [copied, setCopied] = useState(false);
+  const language = className?.replace(/^language-/, "") ?? "";
+  const handleCopy = async () => {
+    const raw =
+      typeof children === "string" ? children : String(children ?? "");
+    try {
+      await navigator.clipboard.writeText(raw.replace(/\n$/, ""));
+      setCopied(true);
+      setTimeout(() => setCopied(false), 1500);
+    } catch {
+      // ignore
+    }
+  };
+  return (
+    <div className="relative my-3 rounded-lg border border-border bg-bg-secondary overflow-hidden">
+      <div className="flex items-center justify-between px-3 py-1.5 bg-neutral-100 border-b border-border">
+        <span className="text-[11px] font-medium text-text-secondary uppercase tracking-wide">
+          {language || "code"}
+        </span>
+        <button
+          type="button"
+          onClick={handleCopy}
+          aria-label={copied ? "Copied" : "Copy code"}
+          title={copied ? "Copied" : "Copy code"}
+          className="p-1 rounded text-text-secondary hover:text-text-primary hover:bg-neutral-200 transition-colors cursor-pointer"
+        >
+          {copied ? (
+            <CheckLineIcon className="w-3.5 h-3.5 text-status-success" />
+          ) : (
+            <CopyIcon className="w-3.5 h-3.5" />
+          )}
+        </button>
+      </div>
+      <pre className="overflow-x-auto px-3 py-2.5 text-[13px] leading-relaxed">
+        <code className={className}>{children}</code>
+      </pre>
+    </div>
+  );
+}
+
+const components: Components = {
+  p: ({ children }) => (
+    <p className="my-2 first:mt-0 last:mb-0 leading-relaxed">{children}</p>
+  ),
+  strong: ({ children }) => (
+    <strong className="font-semibold text-text-primary">{children}</strong>
+  ),
+  em: ({ children }) => <em className="italic">{children}</em>,
+  a: ({ href, children }) => (
+    <a
+      href={href}
+      target="_blank"
+      rel="noopener noreferrer"
+      className="text-accent-primary underline underline-offset-2 hover:text-accent-secondary"
+    >
+      {children}
+    </a>
+  ),
+  ul: ({ children }) => (
+    <ul className="my-2 list-disc pl-5 space-y-1">{children}</ul>
+  ),
+  ol: ({ children }) => (
+    <ol className="my-2 list-decimal pl-5 space-y-1">{children}</ol>
+  ),
+  li: ({ children }) => <li className="leading-relaxed">{children}</li>,
+  h1: ({ children }) => (
+    <h1 className="mt-4 mb-2 text-xl font-semibold text-text-primary">
+      {children}
+    </h1>
+  ),
+  h2: ({ children }) => (
+    <h2 className="mt-4 mb-2 text-lg font-semibold text-text-primary">
+      {children}
+    </h2>
+  ),
+  h3: ({ children }) => (
+    <h3 className="mt-3 mb-1.5 text-base font-semibold text-text-primary">
+      {children}
+    </h3>
+  ),
+  h4: ({ children }) => (
+    <h4 className="mt-3 mb-1.5 text-[15px] font-semibold text-text-primary">
+      {children}
+    </h4>
+  ),
+  blockquote: ({ children }) => (
+    <blockquote className="my-2 border-l-4 border-border pl-3 italic text-text-secondary">
+      {children}
+    </blockquote>
+  ),
+  hr: () => <hr className="my-3 border-border" />,
+  table: ({ children }) => (
+    <div className="my-3 overflow-x-auto">
+      <table className="w-full border-collapse text-[13px]">{children}</table>
+    </div>
+  ),
+  thead: ({ children }) => (
+    <thead className="bg-bg-secondary">{children}</thead>
+  ),
+  th: ({ children }) => (
+    <th className="border border-border px-2 py-1.5 text-left font-semibold">
+      {children}
+    </th>
+  ),
+  td: ({ children }) => (
+    <td className="border border-border px-2 py-1.5 align-top">{children}</td>
+  ),
+  code: ({ className, children, ...rest }) => {
+    const isBlock = /language-/.test(className ?? "");
+    if (isBlock) {
+      return <CodeBlock className={className}>{children}</CodeBlock>;
+    }
+    return (
+      <code
+        className="px-1 py-0.5 rounded bg-bg-secondary border border-border text-[0.9em] font-mono"
+        {...rest}
+      >
+        {children}
+      </code>
+    );
+  },
+  pre: ({ children }) => <>{children}</>,
+};
+
+export default function MarkdownContent({
+  text,
+  className,
+  trailing,
+}: MarkdownContentProps) {
+  return (
+    <div
+      className={`${className ?? ""} wrap-break-word [&_pre]:whitespace-pre-wrap`}
+    >
+      <ReactMarkdown
+        remarkPlugins={[remarkGfm]}
+        rehypePlugins={[rehypeHighlight]}
+        components={components}
+      >
+        {text}
+      </ReactMarkdown>
+      {trailing}
+    </div>
+  );
+}
diff --git a/app/components/chat/VoiceInput.tsx b/app/components/chat/VoiceInput.tsx
index 561717f..71f968a 100644
--- a/app/components/chat/VoiceInput.tsx
+++ b/app/components/chat/VoiceInput.tsx
@@ -103,7 +103,7 @@ export default function VoiceInput({
             aria-label="Send voice message"
             className={`shrink-0 w-9 h-9 rounded-full flex items-center justify-center transition-colors ${
               canSubmit
-                ? "bg-text-primary text-white hover:bg-neutral-800 cursor-pointer"
+                ? "bg-accent-primary text-white hover:bg-accent-secondary cursor-pointer"
                 : "bg-neutral-200 text-text-secondary cursor-not-allowed"
             }`}
           >
diff --git a/app/components/chat/index.ts b/app/components/chat/index.ts
index 241de39..1133616 100644
--- a/app/components/chat/index.ts
+++ b/app/components/chat/index.ts
@@ -3,3 +3,9 @@ export { default as ChatMessageList } from "./ChatMessageList";
 export { default as ChatInput } from "./ChatInput";
 export { default as ChatConfigPicker } from "./ChatConfigPicker";
 export { default as ChatEmptyState } from "./ChatEmptyState";
+export { default as VoiceInput } from "./VoiceInput";
+export { default as MarkdownContent } from "./MarkdownContent";
+export { default as AttachmentChip } from "./AttachmentChip";
+export type { AttachmentChipFile } from "./AttachmentChip";
+export { default as AttachmentPreviewModal } from "./AttachmentPreviewModal";
+export type { PreviewableAttachment } from "./AttachmentPreviewModal";
diff --git a/app/globals.css b/app/globals.css
index e52ddf0..bd9ea2e 100644
--- a/app/globals.css
+++ b/app/globals.css
@@ -1,4 +1,5 @@
 @import "tailwindcss";
+@import "highlight.js/styles/github.css";
 
 :root {
   --background: #ffffff;
diff --git a/app/lib/chatClient.ts b/app/lib/chatClient.ts
index 84ae90e..1f9fac3 100644
--- a/app/lib/chatClient.ts
+++ b/app/lib/chatClient.ts
@@ -86,9 +86,11 @@ export async function pollLLMCall(
     }
     if (FAILURE_STATUSES.has(status)) {
       throw new Error(
-        res.data.error_message ||
-          res.error ||
-          `Job ${status}. Please try again.`,
+        sanitizeAssistantText(
+          res.data.error_message ||
+            res.error ||
+            `Job ${status}. Please try again.`,
+        ),
       );
     }
 
@@ -156,14 +158,24 @@ function findText(node: unknown, depth = 0): string | null {
   return null;
 }
 
+const DATA_URL_RE = /data:([\w.+-]+\/[\w.+-]+);base64,[A-Za-z0-9+/=]{32,}/g;
+
+function sanitizeAssistantText(text: string): string {
+  return text.replace(DATA_URL_RE, (_match, mime: string) => {
+    const [, sub] = mime.split("/");
+    const label = (sub ?? mime).toUpperCase();
+    return `[${label} attachment]`;
+  });
+}
+
 export function extractAssistantText(
   response?: LLMResponseBody | null,
 ): string {
   if (!response) return "";
   const text = findText(response.output);
-  if (text) return text;
+  if (text) return sanitizeAssistantText(text);
   try {
-    return JSON.stringify(response.output ?? "");
+    return sanitizeAssistantText(JSON.stringify(response.output ?? ""));
   } catch {
     return "";
   }
diff --git a/app/lib/types/chat.ts b/app/lib/types/chat.ts
index 8db36fb..0c25ccb 100644
--- a/app/lib/types/chat.ts
+++ b/app/lib/types/chat.ts
@@ -9,6 +9,15 @@ export interface ChatAudioPayload {
   mimeType: string;
 }
 
+export type ChatAttachmentKind = "image" | "pdf";
+
+export interface ChatAttachment {
+  kind: ChatAttachmentKind;
+  name: string;
+  mimeType: string;
+  previewUrl?: string;
+}
+
 export interface ChatMessage {
   id: string;
   role: ChatRole;
@@ -19,6 +28,7 @@ export interface ChatMessage {
   error?: string;
   isVoice?: boolean;
   audio?: ChatAudioPayload;
+  attachments?: ChatAttachment[];
 }
 
 export interface ChatConfigSelection {
@@ -26,8 +36,15 @@ export interface ChatConfigSelection {
   version: number;
 }
 
+export interface SendAttachment {
+  kind: ChatAttachmentKind;
+  name: string;
+  mimeType: string;
+  base64: string;
+}
+
 export type SendInput =
-  | { kind: "text"; text: string }
+  | { kind: "text"; text: string; attachments?: SendAttachment[] }
   | {
       kind: "audio";
       base64: string;
diff --git a/package-lock.json b/package-lock.json
index ec1ccdc..6510ab3 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -11,10 +11,14 @@
         "@react-oauth/google": "^0.13.4",
         "date-fns": "^4.1.0",
         "date-fns-tz": "^3.2.0",
+        "highlight.js": "^11.11.1",
         "next": "^16.0.7",
         "react": "19.2.0",
         "react-dom": "19.2.0",
+        "react-markdown": "^10.1.0",
         "react-router-dom": "^7.9.5",
+        "rehype-highlight": "^7.0.2",
+        "remark-gfm": "^4.0.1",
         "swr": "^2.3.6",
         "zustand": "^5.0.12"
       },
@@ -1561,13 +1565,39 @@
         "tslib": "^2.4.0"
       }
     },
+    "node_modules/@types/debug": {
+      "version": "4.1.13",
+      "resolved": "https://registry.npmjs.org/@types/debug/-/debug-4.1.13.tgz",
+      "integrity": "sha512-KSVgmQmzMwPlmtljOomayoR89W4FynCAi3E8PPs7vmDVPe84hT+vGPKkJfThkmXs0x0jAaa9U8uW8bbfyS2fWw==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/ms": "*"
+      }
+    },
     "node_modules/@types/estree": {
       "version": "1.0.8",
       "resolved": "https://registry.npmjs.org/@types/estree/-/estree-1.0.8.tgz",
       "integrity": "sha512-dWHzHa2WqEXI/O1E9OjrocMTKJl2mSrEolh1Iomrv6U+JuNwaHXsXx9bLu5gG7BUWFIN0skIQJQ/L1rIex4X6w==",
-      "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/estree-jsx": {
+      "version": "1.0.5",
+      "resolved": "https://registry.npmjs.org/@types/estree-jsx/-/estree-jsx-1.0.5.tgz",
+      "integrity": "sha512-52CcUVNFyfb1A2ALocQw/Dd1BQFNmSdkuC3BkZ6iqhdMfQz7JWOFRuJFloOzjk+6WijU56m9oKXFAXc7o3Towg==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/estree": "*"
+      }
+    },
+    "node_modules/@types/hast": {
+      "version": "3.0.4",
+      "resolved": "https://registry.npmjs.org/@types/hast/-/hast-3.0.4.tgz",
+      "integrity": "sha512-WPs+bbQw5aCj+x6laNGWLH3wviHtoCv/P3+otBhbOhJgG8qtpdAMlTCxLtsTWA7LH1Oh/bFCHsBn0TPS5m30EQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "*"
+      }
+    },
     "node_modules/@types/json-schema": {
       "version": "7.0.15",
       "resolved": "https://registry.npmjs.org/@types/json-schema/-/json-schema-7.0.15.tgz",
@@ -1582,6 +1612,21 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/mdast": {
+      "version": "4.0.4",
+      "resolved": "https://registry.npmjs.org/@types/mdast/-/mdast-4.0.4.tgz",
+      "integrity": "sha512-kGaNbPh1k7AFzgpud/gMdvIm5xuECykRR+JnWKQno9TAXVa6WIVCGTPvYGekIDL4uwCZQSYbUxNBSb1aUo79oA==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "*"
+      }
+    },
+    "node_modules/@types/ms": {
+      "version": "2.1.0",
+      "resolved": "https://registry.npmjs.org/@types/ms/-/ms-2.1.0.tgz",
+      "integrity": "sha512-GsCCIZDE/p3i96vtEqx+7dBUGXrc7zeSK3wwPHIaRThS+9OhWIXRqzs4d6k1SVU8g91DrNRWxWUGhp5KXQb2VA==",
+      "license": "MIT"
+    },
     "node_modules/@types/node": {
       "version": "20.19.24",
       "resolved": "https://registry.npmjs.org/@types/node/-/node-20.19.24.tgz",
@@ -1596,7 +1641,6 @@
       "version": "19.2.2",
       "resolved": "https://registry.npmjs.org/@types/react/-/react-19.2.2.tgz",
       "integrity": "sha512-6mDvHUFSjyT2B2yeNx2nUgMxh9LtOWvkhIU3uePn2I2oyNymUAX1NIsdgviM4CH+JSrp2D2hsMvJOkxY+0wNRA==",
-      "devOptional": true,
       "license": "MIT",
       "dependencies": {
         "csstype": "^3.0.2"
@@ -1612,6 +1656,12 @@
         "@types/react": "^19.2.0"
       }
     },
+    "node_modules/@types/unist": {
+      "version": "3.0.3",
+      "resolved": "https://registry.npmjs.org/@types/unist/-/unist-3.0.3.tgz",
+      "integrity": "sha512-ko/gIFJRv177XgZsZcBwnqJN5x/Gien8qNOn0D5bQU/zAzVf9Zt3BlcUiLqhV9y4ARk0GbT3tnUiPNgnTXzc/Q==",
+      "license": "MIT"
+    },
     "node_modules/@typescript-eslint/eslint-plugin": {
       "version": "8.49.0",
       "resolved": "https://registry.npmjs.org/@typescript-eslint/eslint-plugin/-/eslint-plugin-8.49.0.tgz",
@@ -1881,6 +1931,12 @@
         "url": "https://opencollective.com/typescript-eslint"
       }
     },
+    "node_modules/@ungap/structured-clone": {
+      "version": "1.3.1",
+      "resolved": "https://registry.npmjs.org/@ungap/structured-clone/-/structured-clone-1.3.1.tgz",
+      "integrity": "sha512-mUFwbeTqrVgDQxFveS+df2yfap6iuP20NAKAsBt5jDEoOTDew+zwLAOilHCeQJOVSvmgCX4ogqIrA0mnyr08yQ==",
+      "license": "ISC"
+    },
     "node_modules/@unrs/resolver-binding-android-arm-eabi": {
       "version": "1.11.1",
       "resolved": "https://registry.npmjs.org/@unrs/resolver-binding-android-arm-eabi/-/resolver-binding-android-arm-eabi-1.11.1.tgz",
@@ -2436,6 +2492,16 @@
         "node": ">= 0.4"
       }
     },
+    "node_modules/bail": {
+      "version": "2.0.2",
+      "resolved": "https://registry.npmjs.org/bail/-/bail-2.0.2.tgz",
+      "integrity": "sha512-0xO6mYd7JB2YesxDKplafRpsiOzPt9V02ddPCLbY1xYGPOX24NTyN50qnUxgCPcSoYMhKpAuBTjQoRZCAkUDRw==",
+      "license": "MIT",
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/wooorm"
+      }
+    },
     "node_modules/balanced-match": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/balanced-match/-/balanced-match-1.0.2.tgz",
@@ -2614,6 +2680,16 @@
       ],
       "license": "CC-BY-4.0"
     },
+    "node_modules/ccount": {
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/ccount/-/ccount-2.0.1.tgz",
+      "integrity": "sha512-eyrF0jiFpY+3drT6383f1qhkbGsLSifNAjA61IUjZjmLCWjItY6LB9ft9YhoDgwfmclB2zhu51Lc7+95b8NRAg==",
+      "license": "MIT",
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/wooorm"
+      }
+    },
     "node_modules/chalk": {
       "version": "4.1.2",
       "resolved": "https://registry.npmjs.org/chalk/-/chalk-4.1.2.tgz",
@@ -2631,6 +2707,46 @@
         "url": "https://github.com/chalk/chalk?sponsor=1"
       }
     },
+    "node_modules/character-entities": {
+      "version": "2.0.2",
+      "resolved": "https://registry.npmjs.org/character-entities/-/character-entities-2.0.2.tgz",
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@@ -6099,6 +7356,89 @@
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@@ -6581,6 +7921,16 @@
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+      "funding": {
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@@ -6725,6 +8075,20 @@
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@@ -6777,6 +8141,24 @@
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@@ -6931,6 +8313,26 @@
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+      "license": "MIT",
+      "funding": {
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+        "url": "https://github.com/sponsors/wooorm"
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+      "license": "MIT",
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/wooorm"
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@@ -7131,6 +8533,107 @@
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@@ -7216,6 +8719,34 @@
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@@ -7418,6 +8949,16 @@
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+      "license": "MIT",
+      "funding": {
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+        "url": "https://github.com/sponsors/wooorm"
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   }
 }
diff --git a/package.json b/package.json
index c1dfc47..fcdd376 100644
--- a/package.json
+++ b/package.json
@@ -16,10 +16,14 @@
     "@react-oauth/google": "^0.13.4",
     "date-fns": "^4.1.0",
     "date-fns-tz": "^3.2.0",
+    "highlight.js": "^11.11.1",
     "next": "^16.0.7",
     "react": "19.2.0",
     "react-dom": "19.2.0",
+    "react-markdown": "^10.1.0",
     "react-router-dom": "^7.9.5",
+    "rehype-highlight": "^7.0.2",
+    "remark-gfm": "^4.0.1",
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