diff --git a/deploy/nginx-hicad-zoo-ws.conf.template b/deploy/nginx-hicad-zoo-ws.conf.template
index 2d10cda7b..0b4147cb5 100644
--- a/deploy/nginx-hicad-zoo-ws.conf.template
+++ b/deploy/nginx-hicad-zoo-ws.conf.template
@@ -1,7 +1,7 @@
 # Include inside the authenticated HiCAD HTTPS server block.
 # Replace __AI_CAD_WS_PROXY_SECRET__ during deployment and chmod the rendered file 600.
 
-location ^~ /vendor/zoo-modeling-app/assets/ {
+location ^~ /vendor/zoo-modeling-app/assets {
     root /var/www/ai-chatbot/public;
     try_files $uri =404;
     gzip_static on;
diff --git a/scripts/cache-bust-zoo-modeling-app-assets.mjs b/scripts/cache-bust-zoo-modeling-app-assets.mjs
index 98dbe158b..d950add27 100644
--- a/scripts/cache-bust-zoo-modeling-app-assets.mjs
+++ b/scripts/cache-bust-zoo-modeling-app-assets.mjs
@@ -1,44 +1,77 @@
 #!/usr/bin/env node
 
 import { createHash } from "node:crypto";
-import { readFileSync, writeFileSync } from "node:fs";
+import {
+  cpSync,
+  existsSync,
+  readFileSync,
+  renameSync,
+  rmSync,
+  writeFileSync,
+} from "node:fs";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
 
 const assetReferencePattern =
-  /(\b(?:src|href)=")(\.\/assets\/[^"?]+\.(?:css|js))(?:\?v=[^"]+)?(")/g;
+  /(\b(?:src|href)=")(\.\/assets\/([^"?]+\.(?:css|js)))(?:\?v=[^"]+)?(")/g;
 
-export function cacheBustZooModelingAppAssets(outputDir) {
+export function cacheBustZooModelingAppAssets(
+  outputDir,
+  { retainOriginalAssets = false } = {}
+) {
   const indexPath = path.join(outputDir, "index.html");
   const source = readFileSync(indexPath, "utf8");
-  let versionedAssetCount = 0;
+  const assetReferences = [...source.matchAll(assetReferencePattern)];
+
+  if (assetReferences.length === 0) {
+    const currentVersion = source.match(/\.\/assets-([a-f0-9]{12})\//)?.[1];
+    if (currentVersion) {
+      return { assetCount: 0, version: currentVersion };
+    }
+    throw new Error(`No HiCAD entry assets found in ${indexPath}`);
+  }
+
+  const assetsDir = path.join(outputDir, "assets");
+  const contentHash = createHash("sha256");
+  for (const reference of assetReferences.sort((a, b) =>
+    a[3].localeCompare(b[3])
+  )) {
+    contentHash.update(reference[3]);
+    contentHash.update(readFileSync(path.join(assetsDir, reference[3])));
+  }
+
+  const version = contentHash.digest("hex").slice(0, 12);
+  const versionedAssetsName = `assets-${version}`;
+  const versionedAssetsDir = path.join(outputDir, versionedAssetsName);
+  rmSync(versionedAssetsDir, { force: true, recursive: true });
+  if (retainOriginalAssets) {
+    cpSync(assetsDir, versionedAssetsDir, { recursive: true });
+  } else {
+    renameSync(assetsDir, versionedAssetsDir);
+  }
 
   const versionedSource = source.replace(
     assetReferencePattern,
-    (_match, prefix, assetReference, suffix) => {
-      const assetPath = path.join(outputDir, assetReference.slice(2));
-      const version = createHash("sha256")
-        .update(readFileSync(assetPath))
-        .digest("hex")
-        .slice(0, 12);
-      versionedAssetCount += 1;
-      return `${prefix}${assetReference}?v=${version}${suffix}`;
-    }
+    (_match, prefix, _assetReference, assetPath, suffix) =>
+      `${prefix}./${versionedAssetsName}/${assetPath}${suffix}`
   );
-
-  if (versionedAssetCount === 0) {
-    throw new Error(`No versioned HiCAD assets found in ${indexPath}`);
-  }
-
   writeFileSync(indexPath, versionedSource);
-  return versionedAssetCount;
+  return { assetCount: assetReferences.length, version };
 }
 
 const invokedPath = process.argv[1] ? path.resolve(process.argv[1]) : "";
 if (invokedPath === fileURLToPath(import.meta.url)) {
   const outputDir = path.resolve(
-    process.argv[2] || "public/vendor/zoo-modeling-app"
+    process.argv.slice(2).find((argument) => !argument.startsWith("--")) ||
+      "public/vendor/zoo-modeling-app"
+  );
+  if (!existsSync(outputDir)) {
+    throw new Error(`HiCAD output directory does not exist: ${outputDir}`);
+  }
+  const { assetCount, version } = cacheBustZooModelingAppAssets(outputDir, {
+    retainOriginalAssets: process.argv.includes("--retain-original"),
+  });
+  console.log(
+    `Versioned ${assetCount} HiCAD entry assets as assets-${version} in ${outputDir}`
   );
-  const assetCount = cacheBustZooModelingAppAssets(outputDir);
-  console.log(`Versioned ${assetCount} HiCAD entry assets in ${outputDir}`);
 }
diff --git a/scripts/vendor-zoo-modeling-app.mjs b/scripts/vendor-zoo-modeling-app.mjs
index dfeddebe8..10b412827 100644
--- a/scripts/vendor-zoo-modeling-app.mjs
+++ b/scripts/vendor-zoo-modeling-app.mjs
@@ -301,8 +301,7 @@ function ensureWasm() {
   copyFileSync(wasmBinary, path.join(sourceDir, "public/kcl_wasm_lib_bg.wasm"));
 }
 
-function precompressVersionedAssets() {
-  const assetsDir = path.join(outputDir, "assets");
+function precompressVersionedAssets(assetsDir) {
   for (const entry of readdirSync(assetsDir, { withFileTypes: true })) {
     if (!entry.isFile() || !/\.(?:css|js)$/.test(entry.name)) {
       continue;
@@ -339,12 +338,12 @@ async function main() {
   if (!existsSync(path.join(buildDir, "index.html"))) {
     throw new Error("Zoo Design Studio build did not produce index.html");
   }
+  precompressVersionedAssets(path.join(buildDir, "assets"));
   cacheBustZooModelingAppAssets(buildDir);
 
   rmSync(outputDir, { force: true, recursive: true });
   mkdirSync(path.dirname(outputDir), { recursive: true });
   await cp(buildDir, outputDir, { recursive: true });
-  precompressVersionedAssets();
 
   const license = path.join(sourceDir, "LICENSE");
   if (existsSync(license)) {