diff --git a/.planning/REQUIREMENTS.md b/.planning/REQUIREMENTS.md
index 56c36de8..6bc56e51 100644
--- a/.planning/REQUIREMENTS.md
+++ b/.planning/REQUIREMENTS.md
@@ -90,10 +90,10 @@
 - [x] **FILE-05** — File upload from chat input via drag-and-drop or button; file is stored on disk and its metadata is written to libSQL
 - [x] **FILE-06** — Inline file preview in chat: images render inline, PDFs show a first-page preview, code files show a syntax-highlighted preview
 - [x] **FILE-07** — One-click file download from chat for any attached or generated file
-- [ ] **FILE-08** — Agent-generated files (code output, specs, presentations) stored in `files/projects/<slug>/generated/`, linked to the originating task and conversation in libSQL
+- [x] **FILE-08** — Agent-generated files (code output, specs, presentations) stored in `files/projects/<slug>/generated/`, linked to the originating task and conversation in libSQL
 - [x] **FILE-09** — Git integration: `files/` is a git repository; every file operation (upload, generate, replace, delete) creates a commit with a descriptive message
 - [x] **FILE-10** — Version history: user can view the git log for any file and see its change history
-- [ ] **FILE-11** — Placeholder asset tracking: Nexus auto-maintains a `PLACEHOLDERS.md` manifest in each project directory; when a placeholder is replaced by a final asset, the manifest and DB are updated with the replacement chain
+- [x] **FILE-11** — Placeholder asset tracking: Nexus auto-maintains a `PLACEHOLDERS.md` manifest in each project directory; when a placeholder is replaced by a final asset, the manifest and DB are updated with the replacement chain
 - [x] **FILE-12** — File scope promotion: a chat-scoped file can be promoted to a project scope; a project file can be referenced in any chat conversation
 - [x] **FILE-13** — Cross-device file access: files are served via the Nexus server API so a file uploaded on one device is accessible on any other device on the network
 
@@ -175,9 +175,9 @@ The following are explicitly deferred:
 | FILE-05 | Phase 25 | Complete |
 | FILE-06 | Phase 25 | Complete |
 | FILE-07 | Phase 25 | Complete |
-| FILE-08 | Phase 25 | Pending |
+| FILE-08 | Phase 25 | Complete |
 | FILE-09 | Phase 25 | Complete |
 | FILE-10 | Phase 25 | Complete |
-| FILE-11 | Phase 25 | Pending |
+| FILE-11 | Phase 25 | Complete |
 | FILE-12 | Phase 25 | Complete |
 | FILE-13 | Phase 25 | Complete |
diff --git a/server/src/routes/chat-files.ts b/server/src/routes/chat-files.ts
index 7e72814d..d7d26daa 100644
--- a/server/src/routes/chat-files.ts
+++ b/server/src/routes/chat-files.ts
@@ -8,6 +8,8 @@ import { chatFileService, deriveCategory } from "../services/chat-files.js";
 import { chatService } from "../services/chat.js";
 import { isAllowedContentType, MAX_ATTACHMENT_BYTES } from "../attachment-types.js";
 import { assertBoard, assertCompanyAccess } from "./authz.js";
+import { placeholderService } from "../services/placeholder-service.js";
+import { resolveDefaultStorageDir } from "../home-paths.js";
 
 const fileUpload = multer({
   storage: multer.memoryStorage(),
@@ -31,6 +33,8 @@ export function chatFileRoutes(db: Db, storage: StorageService) {
   const router = Router();
   const fileSvc = chatFileService(db);
   const convSvc = chatService(db);
+  const phSvc = placeholderService();
+  const storageDir = resolveDefaultStorageDir();
 
   // POST /conversations/:id/files — Upload a file to a conversation
   router.post("/conversations/:id/files", async (req, res) => {
@@ -96,6 +100,16 @@ export function chatFileRoutes(db: Db, storage: StorageService) {
       projectId: parsedMeta.data.projectId ?? null,
     });
 
+    // Track placeholder if agent-generated and project-scoped
+    if (parsedMeta.data.source === "agent_generated" && chatFile.projectId) {
+      const projectDir = path.join(storageDir, "..", "..", "projects", chatFile.projectId);
+      phSvc.addEntry(projectDir, {
+        fileId: chatFile.id,
+        filename: chatFile.originalFilename,
+        description: "Generated by agent",
+      }).catch(() => {});
+    }
+
     res.status(201).json({
       file: chatFile,
       contentPath: `/api/files/${chatFile.id}/content`,
@@ -205,6 +219,37 @@ export function chatFileRoutes(db: Db, storage: StorageService) {
     res.json(updated);
   });
 
+  // POST /files/:fileId/replace — Replace a placeholder with a final asset
+  router.post("/files/:fileId/replace", async (req, res) => {
+    assertBoard(req);
+    const fileId = req.params.fileId as string;
+    const oldFile = await fileSvc.getById(fileId);
+    if (!oldFile) { res.status(404).json({ error: "File not found" }); return; }
+    assertCompanyAccess(req, oldFile.companyId);
+
+    const { newFileId } = req.body ?? {};
+    if (!newFileId || typeof newFileId !== "string") {
+      res.status(400).json({ error: "newFileId is required" }); return;
+    }
+    const newFile = await fileSvc.getById(newFileId);
+    if (!newFile) { res.status(404).json({ error: "Replacement file not found" }); return; }
+
+    // Update placeholder manifest if project-scoped
+    if (oldFile.projectId) {
+      const projectDir = path.join(storageDir, "..", "..", "projects", oldFile.projectId);
+      await phSvc.replaceEntry(projectDir, fileId, newFileId);
+    }
+
+    // Create reference linking replacement to original context
+    await fileSvc.createReference({
+      fileId: newFileId,
+      conversationId: oldFile.conversationId ?? "",
+      messageId: oldFile.messageId ?? undefined,
+    });
+
+    res.json({ replaced: fileId, replacedBy: newFileId });
+  });
+
   // PATCH /files/:fileId — Attach file to a message (set messageId)
   router.patch("/files/:fileId", async (req, res) => {
     assertBoard(req);