diff --git a/server/src/services/chat.ts b/server/src/services/chat.ts
index 0ccb0004..d0e71e38 100644
--- a/server/src/services/chat.ts
+++ b/server/src/services/chat.ts
@@ -1,6 +1,6 @@
-import { and, asc, desc, eq, gt, ilike, isNull, lt, lte, sql } from "drizzle-orm";
+import { and, asc, desc, eq, gt, ilike, inArray, isNull, lt, lte, sql } from "drizzle-orm";
 import type { Db } from "@paperclipai/db";
-import { agents, chatConversations, chatMessageBookmarks, chatMessages } from "@paperclipai/db";
+import { agents, chatConversations, chatFiles, chatMessageBookmarks, chatMessages } from "@paperclipai/db";
 import { notFound } from "../errors.js";
 
 export function chatService(db: Db) {
@@ -132,7 +132,33 @@ export function chatService(db: Db) {
       const items = hasMore ? rows.slice(0, limit) : rows;
       const nextCursor = hasMore ? items[items.length - 1]!.createdAt.toISOString() : null;
 
-      return { items, hasMore, nextCursor };
+      // Load files for these messages and attach them
+      const messageIds = items.map((m) => m.id);
+      let filesByMessageId = new Map<string, typeof chatFiles.$inferSelect[]>();
+      if (messageIds.length > 0) {
+        const fileRows = await db
+          .select()
+          .from(chatFiles)
+          .where(inArray(chatFiles.messageId, messageIds))
+          .orderBy(asc(chatFiles.createdAt));
+        for (const f of fileRows) {
+          if (!f.messageId) continue;
+          const existing = filesByMessageId.get(f.messageId) ?? [];
+          existing.push(f);
+          filesByMessageId.set(f.messageId, existing);
+        }
+      }
+
+      const itemsWithFiles = items.map((m) => ({
+        ...m,
+        files: (filesByMessageId.get(m.id) ?? []).map((f) => ({
+          ...f,
+          createdAt: f.createdAt.toISOString(),
+          updatedAt: f.updatedAt.toISOString(),
+        })),
+      }));
+
+      return { items: itemsWithFiles, hasMore, nextCursor };
     },
 
     async addMessage(
@@ -164,7 +190,7 @@ export function chatService(db: Db) {
           .where(and(eq(chatConversations.id, conversationId), isNull(chatConversations.title)));
       }
 
-      return message!;
+      return { ...message!, files: [] };
     },
 
     async editMessage(messageId: string, content: string) {
diff --git a/ui/src/api/chat.ts b/ui/src/api/chat.ts
index e584df62..a7a4db0b 100644
--- a/ui/src/api/chat.ts
+++ b/ui/src/api/chat.ts
@@ -213,6 +213,14 @@ export const chatApi = {
     return `/api/conversations/${conversationId}/export?format=${format}`;
   },
 
+  async attachFilesToMessage(fileIds: string[], messageId: string) {
+    await Promise.all(
+      fileIds.map((fileId) =>
+        api.patch(`/files/${fileId}`, { messageId })
+      )
+    );
+  },
+
   async uploadFile(
     conversationId: string,
     file: File,
diff --git a/ui/src/components/ChatMessage.tsx b/ui/src/components/ChatMessage.tsx
index febae610..32558e99 100644
--- a/ui/src/components/ChatMessage.tsx
+++ b/ui/src/components/ChatMessage.tsx
@@ -7,9 +7,10 @@ import { ChatSpecCard } from "./ChatSpecCard";
 import { ChatHandoffIndicator } from "./ChatHandoffIndicator";
 import { ChatTaskCreatedBadge } from "./ChatTaskCreatedBadge";
 import { ChatStatusUpdateBadge } from "./ChatStatusUpdateBadge";
+import { ChatFilePreview } from "./ChatFilePreview";
 import { Button } from "@/components/ui/button";
 import { cn } from "../lib/utils";
-import type { AgentRole } from "@paperclipai/shared";
+import type { AgentRole, ChatFile } from "@paperclipai/shared";
 
 interface ChatMessageProps {
   id?: string;
@@ -28,6 +29,7 @@ interface ChatMessageProps {
   onHandoff?: (spec: { what: string; why: string; constraints: string; success: string }) => void;
   onBookmark?: (messageId: string) => void;
   isBookmarked?: boolean;
+  files?: ChatFile[];
 }
 
 export function ChatMessage({
@@ -47,6 +49,7 @@ export function ChatMessage({
   onHandoff,
   onBookmark,
   isBookmarked,
+  files,
 }: ChatMessageProps) {
   const [isEditing, setIsEditing] = useState(false);
   const [editValue, setEditValue] = useState(content);
@@ -135,6 +138,17 @@ export function ChatMessage({
           )}
         >
           {content}
+          {files && files.length > 0 && (
+            <div className="mt-2 flex flex-col gap-2">
+              {files.map((f) => (
+                <ChatFilePreview
+                  key={f.id}
+                  file={f}
+                  contentPath={`/api/files/${f.id}/content`}
+                />
+              ))}
+            </div>
+          )}
           <ChatMessageActions
             role="user"
             isStreaming={isAnyStreaming}
@@ -160,6 +174,17 @@ export function ChatMessage({
         />
       )}
       <ChatMarkdownMessage content={content} />
+      {files && files.length > 0 && (
+        <div className="mt-2 flex flex-col gap-2">
+          {files.map((f) => (
+            <ChatFilePreview
+              key={f.id}
+              file={f}
+              contentPath={`/api/files/${f.id}/content`}
+            />
+          ))}
+        </div>
+      )}
       {isStreaming && <ChatStreamingCursor />}
       <ChatMessageActions
         role="assistant"
diff --git a/ui/src/components/ChatMessageList.tsx b/ui/src/components/ChatMessageList.tsx
index 53b2d2c9..69e6cbaa 100644
--- a/ui/src/components/ChatMessageList.tsx
+++ b/ui/src/components/ChatMessageList.tsx
@@ -177,6 +177,7 @@ export function ChatMessageList({
                   onHandoff={onHandoff}
                   onBookmark={onBookmark}
                   isBookmarked={msg.id ? (bookmarkedMessageIds?.has(msg.id) ?? false) : false}
+                  files={msg.files}
                 />
               </div>
             );
diff --git a/ui/src/components/ChatPanel.tsx b/ui/src/components/ChatPanel.tsx
index 787f7859..8b8236d2 100644
--- a/ui/src/components/ChatPanel.tsx
+++ b/ui/src/components/ChatPanel.tsx
@@ -19,6 +19,7 @@ import { useChatMessages } from "../hooks/useChatMessages";
 import { useStreamingChat } from "../hooks/useStreamingChat";
 import { useBrainstormerDefault } from "../hooks/useBrainstormerDefault";
 import { useChatBookmarks, useToggleBookmark } from "../hooks/useChatBookmarks";
+import { useChatFileUpload } from "../hooks/useChatFileUpload";
 import { resolveAgentFromContent } from "../lib/slash-commands";
 import type { AgentRole } from "@paperclipai/shared";
 
@@ -34,6 +35,7 @@ export function ChatPanel() {
 
   const { messages } = useChatMessages(activeConversationId);
   const { streamingContent, isStreaming, startStream, stop } = useStreamingChat(activeConversationId);
+  const { pendingFiles, addFile, removeFile, clearCompleted, completedFileIds } = useChatFileUpload(activeConversationId);
 
   const brainstormerDefaultId = useBrainstormerDefault();
 
@@ -132,6 +134,9 @@ export function ChatPanel() {
     // Resolve agent from slash command or @mention
     const resolvedAgentId = resolveAgentFromContent(content, agents, activeAgentId);
 
+    // Capture file IDs before clearing
+    const fileIdsToAttach = [...completedFileIds];
+
     setIsSending(true);
     try {
       if (!activeConversationId) {
@@ -140,13 +145,24 @@ export function ChatPanel() {
           agentId: resolvedAgentId ?? undefined,
         });
         setActiveConversationId(newConvo.id);
-        await chatApi.postMessage(newConvo.id, { role: "user", content });
+        const message = await chatApi.postMessage(newConvo.id, { role: "user", content });
+        // Attach any uploaded files to the message
+        if (fileIdsToAttach.length > 0) {
+          await chatApi.attachFilesToMessage(fileIdsToAttach, message.id);
+          clearCompleted();
+          queryClient.invalidateQueries({ queryKey: ["chat", "messages", newConvo.id] });
+        }
         queryClient.invalidateQueries({ queryKey: ["chat"] });
         // Note: streaming starts on next render when activeConversationId is set
         // For now, the echo stream will be triggered by the new conversation
       } else {
         // Path 2: Active conversation -- post user message then stream
-        await chatApi.postMessage(activeConversationId, { role: "user", content });
+        const message = await chatApi.postMessage(activeConversationId, { role: "user", content });
+        // Attach any uploaded files to the message
+        if (fileIdsToAttach.length > 0) {
+          await chatApi.attachFilesToMessage(fileIdsToAttach, message.id);
+          clearCompleted();
+        }
         queryClient.invalidateQueries({ queryKey: ["chat", "messages", activeConversationId] });
         startStream(content, resolvedAgentId ?? undefined);
       }
@@ -369,6 +385,9 @@ export function ChatPanel() {
               placeholder={isStreaming ? "Waiting for response..." : "Message your agent..."}
               agents={agents}
               agentsLoading={agentsLoading}
+              pendingFiles={pendingFiles}
+              onRemoveFile={removeFile}
+              onFilesPicked={(files) => files.forEach(addFile)}
             />
           </div>
         </div>