diff --git a/scripts/check/check-install-upgrade.mjs b/scripts/check/check-install-upgrade.mjs
index a71ccdb1fe..11cdcf9816 100644
--- a/scripts/check/check-install-upgrade.mjs
+++ b/scripts/check/check-install-upgrade.mjs
@@ -76,7 +76,9 @@ const INTERNAL_SERVICE_HEADER = "x-omniroute-internal-service-token";
  * packaged CLI. Sent alongside the internal-service token so a build that only honours one
  * of the two still answers with the full payload.
  */
-function derivePackagedCliToken(prefix) {
+// The CLI token salt lives under <DATA_DIR> (#13679/#13909): derive against the DATA_DIR the
+// probed server boots on, or the token never matches.
+function derivePackagedCliToken(prefix, dataDir) {
   const cliModuleUrl = pathToFileURL(
     path.join(packageRootFor(prefix), "bin", "cli", "utils", "cliToken.mjs")
   ).href;
@@ -89,7 +91,7 @@ function derivePackagedCliToken(prefix) {
         "import(process.argv[1]).then(async m => process.stdout.write(await m.getCliToken()))",
         cliModuleUrl,
       ],
-      { encoding: "utf8", env: { ...process.env } }
+      { encoding: "utf8", env: { ...process.env, DATA_DIR: dataDir } }
     ).trim();
   } catch {
     // A truncated/broken install cannot derive a token. Returning null keeps the boot
@@ -176,7 +178,7 @@ async function bootAndProbe({ prefix, dataDir, port, expectVersion, label }) {
   if (!fs.existsSync(binPath)) {
     return { ok: false, failures: [`${label}: bin not found at ${binPath}`], tail: [] };
   }
-  const cliToken = derivePackagedCliToken(prefix);
+  const cliToken = derivePackagedCliToken(prefix, dataDir);
   const probeHeaders = {
     [INTERNAL_SERVICE_HEADER]: INTERNAL_SERVICE_TOKEN,
     ...(cliToken ? { "x-omniroute-cli-token": cliToken } : {}),
diff --git a/scripts/check/check-pack-boot.mjs b/scripts/check/check-pack-boot.mjs
index 2ca4097a0a..33f85b6ef4 100644
--- a/scripts/check/check-pack-boot.mjs
+++ b/scripts/check/check-pack-boot.mjs
@@ -311,7 +311,13 @@ function spawnServer(binPath, port, dataDir) {
   return { child, tail };
 }
 
-function derivePackagedCliToken(packageRoot) {
+/**
+ * Derive the loopback machine token exactly as the installed CLI would for this install.
+ * Since #13679/#13909 the token salt is per-install, persisted under <DATA_DIR>, so the
+ * derivation MUST see the same DATA_DIR the server boots on — otherwise the CLI resolves
+ * a different salt, the server rejects the token and health serves the anonymous view.
+ */
+export function derivePackagedCliToken(packageRoot, dataDir) {
   const cliModuleUrl = pathToFileURL(
     path.join(packageRoot, "bin", "cli", "utils", "cliToken.mjs")
   ).href;
@@ -323,7 +329,7 @@ function derivePackagedCliToken(packageRoot) {
       "import(process.argv[1]).then(async m => process.stdout.write(await m.getCliToken()))",
       cliModuleUrl,
     ],
-    { encoding: "utf8", env: { ...process.env } }
+    { encoding: "utf8", env: { ...process.env, DATA_DIR: dataDir } }
   ).trim();
 }
 
@@ -454,7 +460,7 @@ async function main() {
     const dataDir = path.join(tmp, "data");
     fs.mkdirSync(dataDir, { recursive: true });
     const binPath = path.join(prefix, "bin", "omniroute");
-    const packagedCliToken = derivePackagedCliToken(packageRoot);
+    const packagedCliToken = derivePackagedCliToken(packageRoot, dataDir);
 
     // BOOT #1 — boot, prove the forced sql.js tier, PATCH a setting, then shut down cleanly
     // so the sql.js adapter's graceful persist actually lands on disk. The in-flow stopChild
diff --git a/tests/unit/check-pack-boot.test.ts b/tests/unit/check-pack-boot.test.ts
index 2a7e0edf07..8c8bce2617 100644
--- a/tests/unit/check-pack-boot.test.ts
+++ b/tests/unit/check-pack-boot.test.ts
@@ -1,7 +1,8 @@
 import { test } from "node:test";
 import assert from "node:assert/strict";
 import { createHmac } from "node:crypto";
-import { readFileSync } from "node:fs";
+import { existsSync, mkdtempSync, readFileSync, rmSync } from "node:fs";
+import os from "node:os";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
 import {
@@ -15,6 +16,7 @@ import {
   evaluateMachineTokenAuth,
   evaluateSqlJsRoundTrip,
   evaluateRestartPersistence,
+  derivePackagedCliToken,
 } from "../../scripts/check/check-pack-boot.mjs";
 
 // WS1.2 (T1, v3.8.49 quality plan) — pure-function guards for the tarball boot-smoke
@@ -244,3 +246,33 @@ test("source guard: final shutdown only deletes the workspace after a CONFIRMED
     "stopChild/waitForHealthy must read authoritative exit state, not a stale boolean"
   );
 });
+
+// #13679/#13909 made the CLI token salt per-install, persisted under <DATA_DIR>. The
+// smoke boots the server on an isolated DATA_DIR, so the token it sends must be derived
+// against that SAME DATA_DIR — derived without it, the CLI resolves a different salt,
+// the server rejects the token, and /api/monitoring/health answers the anonymous view
+// ("version undefined", release PR #11442 Package Artifact).
+test("derivePackagedCliToken derives the token against the server's DATA_DIR salt", () => {
+  const repoRoot = path.resolve(path.dirname(fileURLToPath(import.meta.url)), "../..");
+  const dataDir = mkdtempSync(path.join(os.tmpdir(), "pack-boot-cli-token-"));
+  const otherDataDir = mkdtempSync(path.join(os.tmpdir(), "pack-boot-cli-token-other-"));
+  const savedCliSalt = process.env.OMNIROUTE_CLI_SALT;
+  delete process.env.OMNIROUTE_CLI_SALT;
+  try {
+    const token = derivePackagedCliToken(repoRoot, dataDir);
+    assert.match(token, /^[0-9a-f]{64}$/);
+    assert.equal(
+      existsSync(path.join(dataDir, "cli-token-salt.json")),
+      true,
+      "the salt must be established inside the smoke's DATA_DIR"
+    );
+    // Stable for the same DATA_DIR, different for another install's DATA_DIR.
+    assert.equal(derivePackagedCliToken(repoRoot, dataDir), token);
+    assert.notEqual(derivePackagedCliToken(repoRoot, otherDataDir), token);
+  } finally {
+    if (savedCliSalt === undefined) delete process.env.OMNIROUTE_CLI_SALT;
+    else process.env.OMNIROUTE_CLI_SALT = savedCliSalt;
+    rmSync(dataDir, { recursive: true, force: true });
+    rmSync(otherDataDir, { recursive: true, force: true });
+  }
+});