diff --git a/server/typescript/packages/docs-site/src/load.ts b/server/typescript/packages/docs-site/src/load.ts
index bd32dc003..a3d40d81e 100644
--- a/server/typescript/packages/docs-site/src/load.ts
+++ b/server/typescript/packages/docs-site/src/load.ts
@@ -1,8 +1,9 @@
-import { mkdtempSync, rmSync, symlinkSync } from "node:fs";
+import { mkdtempSync, readdirSync, rmSync, statSync, symlinkSync } from "node:fs";
 import { tmpdir } from "node:os";
 import { basename, join, resolve } from "node:path";
 import { MetaDataLoader, composeRegistry, coreTypesProvider, dbProvider, docProvider, promptProvider, uiProvider } from "@metaobjectsdev/metadata";
 import type { MetaData, MetaRoot, MetaDataTypeProvider } from "@metaobjectsdev/metadata";
+import { FileSource } from "@metaobjectsdev/metadata/core";
 
 export interface LoadedModel {
   root: MetaRoot;
@@ -35,7 +36,17 @@ export async function loadModel(
       symlinkSync(resolve(dir), join(staging, baseName));
     }
     const registry = composeRegistry([coreTypesProvider, dbProvider, docProvider, promptProvider, uiProvider, ...extraProviders]);
-    const result = await MetaDataLoader.fromDirectory(staging, { registry, strict: false });
+    // Feed files in files-before-subdirs order (the same order the sdk's loadMemory
+    // uses), NOT fromDirectory's flat basename sort. Cross-file overlays require the
+    // base (typically a top-level file) to load before an overlay that lives in a
+    // nested dir; the basename sort can otherwise process e.g.
+    // `admin-ui/x.admin.yaml` before its base `x.yaml` and fail with
+    // ERR_OVERLAY_NO_TARGET. (fromDirectory's basename order is a cross-port
+    // DirectorySource contract, so we order at this boundary rather than change it.)
+    const files = collectOrderedMetadataFiles(staging);
+    const result = await new MetaDataLoader({ registry, strict: false }).load(
+      files.map((f) => new FileSource(f)),
+    );
     if (result.errors.length > 0) {
       throw new Error(`metadata load failed:\n${result.errors.map((e) => String(e)).join("\n")}`);
     }
@@ -49,6 +60,24 @@ export async function loadModel(
   }
 }
 
+/** Metadata files under `dir`, files-before-subdirs with each level sorted — the
+ *  overlay-safe order the sdk's loadMemory uses, so a base loads before an overlay
+ *  nested under it. Symlinks (the staging dir uses them) are followed. */
+function collectOrderedMetadataFiles(dir: string): string[] {
+  const files: string[] = [];
+  const subdirs: string[] = [];
+  for (const entry of readdirSync(dir)) {
+    const full = join(dir, entry);
+    const s = statSync(full); // follows symlinks — staging entries are symlinked source dirs
+    if (s.isDirectory()) subdirs.push(full);
+    else if (s.isFile() && /\.(json|ya?ml)$/i.test(entry)) files.push(full);
+  }
+  files.sort();
+  const out = [...files];
+  for (const sub of subdirs.sort()) out.push(...collectOrderedMetadataFiles(sub));
+  return out;
+}
+
 /** Which top-level source dir a node came from (first file path segment of its source envelope). */
 export function treeOf(node: MetaData, model: LoadedModel): string {
   const src = node.source as { files?: string[] };
diff --git a/server/typescript/packages/docs-site/test/overlay-order.test.ts b/server/typescript/packages/docs-site/test/overlay-order.test.ts
new file mode 100644
index 000000000..ca42ac0c8
--- /dev/null
+++ b/server/typescript/packages/docs-site/test/overlay-order.test.ts
@@ -0,0 +1,69 @@
+import { expect, test } from "bun:test";
+import { existsSync, mkdtempSync, mkdirSync, writeFileSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { generateSite } from "../src/site";
+import { loadModel } from "../src/load";
+
+// A base object in a TOP-LEVEL file + an `overlay: true` extension in a SUBDIR
+// whose basename ("aaa-overlay.yaml") sorts BEFORE the base ("base.yaml"). Under
+// fromDirectory's flat basename sort the overlay loads first → ERR_OVERLAY_NO_TARGET;
+// the files-before-subdirs order loads the base first so the overlay merges.
+function overlayFixture(): string {
+  const root = mkdtempSync(join(tmpdir(), "docs-overlay-"));
+  const src = join(root, "acme");
+  mkdirSync(join(src, "z-sub"), { recursive: true });
+  writeFileSync(
+    join(src, "base.yaml"),
+    [
+      "metadata:",
+      "  package: acme",
+      "  children:",
+      "    - object.value:",
+      "        name: Widget",
+      "        children:",
+      "          - field.string: { name: id }",
+      "",
+    ].join("\n"),
+  );
+  writeFileSync(
+    join(src, "z-sub", "aaa-overlay.yaml"),
+    [
+      "metadata:",
+      "  package: acme",
+      "  children:",
+      "    - object.value:",
+      "        name: Widget",
+      "        overlay: true",
+      "        children:",
+      "          - field.string: { name: extra }",
+      "",
+    ].join("\n"),
+  );
+  return src;
+}
+
+test("cross-file overlay: base (top-level) loads before an overlay nested in a subdir", async () => {
+  const dir = overlayFixture();
+  const model = await loadModel([dir]);
+  const widget = model.root.objects().find((o) => o.name === "Widget");
+  expect(widget).toBeDefined();
+  const fieldNames = widget!.childrenOfType("field").map((f) => f.name);
+  // base field preserved AND the subdir overlay merged its field in
+  expect(fieldNames).toContain("id");
+  expect(fieldNames).toContain("extra");
+});
+
+test("generateSite succeeds on a model with a subdir overlay", async () => {
+  const dir = overlayFixture();
+  const out = mkdtempSync(join(tmpdir(), "docs-overlay-out-"));
+  const r = await generateSite({
+    sourceDirs: [dir],
+    outDir: out,
+    title: "Fixture",
+    stamp: "2026-01-01",
+    commit: "abc1234",
+  });
+  expect(existsSync(join(out, "index.html"))).toBe(true);
+  expect(r.dangling).toEqual([]);
+});