diff --git a/CHANGELOG.md b/CHANGELOG.md
index e9a10bcd24..23240ceebe 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,7 @@
 ### 🔧 Bug Fixes
 
 - **services (installer):** fix `spawn EINVAL` when installing an embedded service (9Router / CLIProxy) on **Windows + Node.js 24+**. Node 24 stopped letting `child_process.execFile()` run `.cmd` batch files without a shell (nodejs/node#52554), and npm on Windows is `npm.cmd`, so `runNpm()` threw `EINVAL` the moment a user clicked **Install**. `runNpm` now enables `shell` on win32 only. To keep Hard Rule #13 intact under a shell — where the shell, not `execFile`, parses argv — the install `--prefix` (a `DATA_DIR` path that can legitimately contain spaces, e.g. `C:\Users\John Doe\.omniroute\…`) is now passed via the `npm_config_prefix` **environment variable** instead of an argv path, and the user-supplied install `version` is constrained to a dist-tag/semver shape (`SERVICE_VERSION_PATTERN`) at the route boundary so it can never carry shell metacharacters. With the prefix in the environment and the version validated, every remaining argv entry is a static flag. Regression guards: `tests/unit/services/installers/runNpm-shell-5379.test.ts` (+ existing `ninerouter.test.ts` aligned to npm's `npm_config_prefix` env). ([#5379](https://github.com/diegosouzapw/OmniRoute/issues/5379))
+- **cli (serve):** restore `dist/tls-options.mjs` to the npm tarball — the opt-in native HTTPS/TLS sidecar (#5361) was copied into the staged `dist/` by the build but then **pruned** by the prepublish allowlist step, so `omniroute serve` crashed on the published 3.8.41 with `ERR_MODULE_NOT_FOUND` (`dist/server-ws.mjs` imports `./tls-options.mjs`). Added `tls-options.mjs` to `APP_STAGING_ALLOWED_EXACT_PATHS` (survives the prune) and `dist/tls-options.mjs` to `PACK_ARTIFACT_REQUIRED_PATHS` (the `check:pack-artifact` gate now fails loudly if it ever vanishes again — same guard pattern as `webdav-handler.mjs`). Regression guards in `tests/unit/pack-artifact-policy.test.ts`. ([#5452](https://github.com/diegosouzapw/OmniRoute/issues/5452))
 
 ---
 
diff --git a/scripts/build/pack-artifact-policy.ts b/scripts/build/pack-artifact-policy.ts
index ba0451059e..6b0cb27a7e 100644
--- a/scripts/build/pack-artifact-policy.ts
+++ b/scripts/build/pack-artifact-policy.ts
@@ -47,6 +47,11 @@ export const APP_STAGING_ALLOWED_EXACT_PATHS: string[] = [
   "scripts/dev/tls-options.mjs",
   "server.js",
   "server-ws.mjs",
+  // #5452: dist/tls-options.mjs is copied by assembleStandalone (EXTRA_MODULE_ENTRIES)
+  // and imported by dist/server-ws.mjs for opt-in native HTTPS/TLS (#5361). Without
+  // this bare entry the prepublish prune (Step 10.7) deletes it → `omniroute serve`
+  // crashes with ERR_MODULE_NOT_FOUND (regressed in the published 3.8.41 tarball).
+  "tls-options.mjs",
   "webdav-handler.mjs",
 ];
 
@@ -144,6 +149,9 @@ export const PACK_ARTIFACT_REQUIRED_PATHS: string[] = [
   "dist/responses-ws-proxy.mjs",
   "dist/peer-stamp.mjs",
   "dist/http-method-guard.cjs",
+  // #5452: regression guard — make check:pack-artifact fail loudly if the TLS
+  // opt-in sidecar (imported by dist/server-ws.mjs) ever vanishes from the tarball.
+  "dist/tls-options.mjs",
   "dist/webdav-handler.mjs",
   "bin/cli/program.mjs",
   "bin/mcp-server.mjs",
diff --git a/tests/unit/pack-artifact-policy.test.ts b/tests/unit/pack-artifact-policy.test.ts
index cb37b2b66f..098ac4483e 100644
--- a/tests/unit/pack-artifact-policy.test.ts
+++ b/tests/unit/pack-artifact-policy.test.ts
@@ -64,6 +64,22 @@ test("webdav-handler.mjs is allowed in staging dist/ (server-ws.mjs dependency,
   assert.deepEqual(unexpectedPaths, []);
 });
 
+test("tls-options.mjs is allowed in staging dist/ (server-ws.mjs dependency, missed in 3.8.41 build — #5452)", () => {
+  const unexpectedPaths = findUnexpectedArtifactPaths(["tls-options.mjs"], {
+    exactPaths: APP_STAGING_ALLOWED_EXACT_PATHS,
+    prefixPaths: APP_STAGING_ALLOWED_PATH_PREFIXES,
+  });
+  assert.deepEqual(unexpectedPaths, []);
+});
+
+test("dist/tls-options.mjs is a required tarball path (regression guard for #5452)", () => {
+  const missingPaths = findMissingArtifactPaths([], PACK_ARTIFACT_REQUIRED_PATHS);
+  assert.ok(
+    missingPaths.includes("dist/tls-options.mjs"),
+    "dist/tls-options.mjs must be enforced by the pack-artifact gate"
+  );
+});
+
 test("setupPolyfill.ts is allowed in the tarball (bin/omniroute.mjs imports it at startup)", () => {
   const unexpectedPaths = findUnexpectedArtifactPaths(["open-sse/utils/setupPolyfill.ts"], {
     exactPaths: PACK_ARTIFACT_ALLOWED_EXACT_PATHS,
@@ -98,6 +114,7 @@ test("findMissingArtifactPaths flags missing root runtime files in the tarball",
     "dist/peer-stamp.mjs",
     "dist/responses-ws-proxy.mjs",
     "dist/server-ws.mjs",
+    "dist/tls-options.mjs",
     "dist/webdav-handler.mjs",
     "scripts/build/colocateOptionals.mjs",
     "scripts/build/native-binary-compat.mjs",