diff --git a/packages/cli/src/lib/init/tools/list-dir.ts b/packages/cli/src/lib/init/tools/list-dir.ts
index 85f00f5d5..dbdcf77ff 100644
--- a/packages/cli/src/lib/init/tools/list-dir.ts
+++ b/packages/cli/src/lib/init/tools/list-dir.ts
@@ -36,10 +36,17 @@ export async function listDir(payload: ListDirPayload): Promise<ToolResult> {
     maxDepth,
     maxEntries,
     recursive,
+    truncated: false,
   };
 
   await walkDirectory(targetPath, 0, state);
-  return { ok: true, data: { entries: state.entries } };
+  return {
+    ok: true,
+    data: {
+      entries: state.entries,
+      ...(state.truncated ? { truncated: true } : {}),
+    },
+  };
 }
 
 type WalkState = {
@@ -49,13 +56,14 @@ type WalkState = {
   maxDepth: number;
   maxEntries: number;
   recursive: boolean;
+  truncated: boolean;
 };
 
-async function readDirEntries(dir: string): Promise<fs.Dirent[]> {
+async function readDirEntries(dir: string): Promise<fs.Dirent[] | undefined> {
   try {
     return await fs.promises.readdir(dir, { withFileTypes: true });
   } catch {
-    return [];
+    return;
   }
 }
 
@@ -93,24 +101,53 @@ function toDirEntry(
     }
   }
 
+  if (entry.isDirectory()) {
+    return {
+      name: entry.name,
+      path: normalizePath(relNative),
+      type: "directory",
+    };
+  }
+
+  // Only regular files carry size. lstat avoids following a path that changed
+  // into a symlink after readdir; special files are never opened.
   return {
     name: entry.name,
     path: normalizePath(relNative),
-    type: entry.isDirectory() ? "directory" : "file",
+    type: "file",
+    ...(entry.isFile() ? fileSize(abs) : {}),
   };
 }
 
+/** Return a regular file's byte size without opening or reading its contents. */
+function fileSize(abs: string): { size?: number } {
+  try {
+    const stat = fs.lstatSync(abs);
+    return stat.isFile() ? { size: stat.size } : {};
+  } catch {
+    return {};
+  }
+}
+
 async function walkDirectory(
   dir: string,
   depth: number,
   state: WalkState
 ): Promise<void> {
   if (depth > state.maxDepth || state.entries.length >= state.maxEntries) {
+    state.truncated = true;
+    return;
+  }
+
+  const entries = await readDirEntries(dir);
+  if (!entries) {
+    state.truncated = true;
     return;
   }
 
-  for (const entry of await readDirEntries(dir)) {
+  for (const entry of entries) {
     if (state.entries.length >= state.maxEntries) {
+      state.truncated = true;
       return;
     }
     const nextEntry = toDirEntry(state, dir, entry);
@@ -119,7 +156,11 @@ async function walkDirectory(
     }
     state.entries.push(nextEntry);
     if (shouldRecurseInto(entry, state)) {
-      await walkDirectory(dir + NATIVE_SEP + entry.name, depth + 1, state);
+      if (depth >= state.maxDepth) {
+        state.truncated = true;
+      } else {
+        await walkDirectory(dir + NATIVE_SEP + entry.name, depth + 1, state);
+      }
     }
   }
 }
diff --git a/packages/cli/src/lib/init/types.ts b/packages/cli/src/lib/init/types.ts
index e84e53929..f3c46734f 100644
--- a/packages/cli/src/lib/init/types.ts
+++ b/packages/cli/src/lib/init/types.ts
@@ -2,6 +2,9 @@ export type DirEntry = {
   name: string;
   path: string;
   type: "file" | "directory";
+  /** File size in bytes; omitted for directories. Lets the agent skip huge
+   *  files without reading them, like `ls -l`. */
+  size?: number;
 };
 
 export type ExistingProjectData = {
diff --git a/packages/cli/test/lib/init/tools/filesystem-tools.test.ts b/packages/cli/test/lib/init/tools/filesystem-tools.test.ts
index 4142b2daf..ec122acd7 100644
--- a/packages/cli/test/lib/init/tools/filesystem-tools.test.ts
+++ b/packages/cli/test/lib/init/tools/filesystem-tools.test.ts
@@ -1,3 +1,4 @@
+import { execFileSync } from "node:child_process";
 import fs from "node:fs";
 import path from "node:path";
 import { afterEach, beforeEach, describe, expect, test, vi } from "vitest";
@@ -72,9 +73,108 @@ describe("filesystem tools", () => {
 
     expect(result.ok).toBe(true);
     expect(entries.map((entry) => entry.path)).toContain("src/app.ts");
+    expect(entries.find((entry) => entry.path === "src/app.ts")).toMatchObject({
+      size: 18,
+      type: "file",
+    });
     expect(precomputed.map((entry) => entry.path)).toContain("src/app.ts");
   });
 
+  test("reports when a bounded recursive listing is incomplete", async () => {
+    fs.mkdirSync(path.join(testDir, "nested", "deeper"), { recursive: true });
+    fs.writeFileSync(path.join(testDir, "nested", "deeper", "app.ts"), "x");
+    fs.writeFileSync(path.join(testDir, "root.ts"), "x");
+
+    const byDepth = await executeTool(
+      {
+        type: "tool",
+        operation: "list-dir",
+        cwd: testDir,
+        params: { path: ".", recursive: true, maxDepth: 0, maxEntries: 100 },
+      },
+      makeContext(testDir)
+    );
+    const byEntries = await executeTool(
+      {
+        type: "tool",
+        operation: "list-dir",
+        cwd: testDir,
+        params: { path: ".", recursive: true, maxDepth: 10, maxEntries: 1 },
+      },
+      makeContext(testDir)
+    );
+
+    expect(byDepth.data).toMatchObject({ truncated: true });
+    expect(byEntries.data).toMatchObject({ truncated: true });
+    expect((byEntries.data as { entries: unknown[] }).entries).toHaveLength(1);
+  });
+
+  test("reports an unreadable directory as an incomplete listing", async () => {
+    const readdirSpy = vi
+      .spyOn(fs.promises, "readdir")
+      .mockRejectedValueOnce(new Error("permission denied"));
+
+    try {
+      const result = await executeTool(
+        {
+          type: "tool",
+          operation: "list-dir",
+          cwd: testDir,
+          params: { path: ".", recursive: true },
+        },
+        makeContext(testDir)
+      );
+
+      expect(result).toMatchObject({
+        data: { entries: [], truncated: true },
+        ok: true,
+      });
+    } finally {
+      readdirSpy.mockRestore();
+    }
+  });
+
+  test.runIf(process.platform !== "win32")(
+    "lists special files without opening them or attaching a size",
+    async () => {
+      const fifoPath = path.join(testDir, "stream.pipe");
+      execFileSync("mkfifo", [fifoPath]);
+      fs.writeFileSync(path.join(testDir, "regular.ts"), "export {};\n");
+      const openSpy = vi.spyOn(fs, "openSync");
+      const readSpy = vi.spyOn(fs, "readSync");
+
+      try {
+        const result = await executeTool(
+          {
+            type: "tool",
+            operation: "list-dir",
+            cwd: testDir,
+            params: { path: "." },
+          },
+          makeContext(testDir)
+        );
+        const entry = (
+          result.data as { entries: Record<string, unknown>[] }
+        ).entries.find(({ path: entryPath }) => entryPath === "stream.pipe");
+        const regular = (
+          result.data as { entries: Record<string, unknown>[] }
+        ).entries.find(({ path: entryPath }) => entryPath === "regular.ts");
+
+        expect(entry).toEqual({
+          name: "stream.pipe",
+          path: "stream.pipe",
+          type: "file",
+        });
+        expect(regular).toMatchObject({ size: 11, type: "file" });
+        expect(openSpy).not.toHaveBeenCalled();
+        expect(readSpy).not.toHaveBeenCalled();
+      } finally {
+        openSpy.mockRestore();
+        readSpy.mockRestore();
+      }
+    }
+  );
+
   test("reads files and checks existence in batches", async () => {
     fs.writeFileSync(path.join(testDir, "exists.txt"), "hello");