diff --git a/CHANGELOG.md b/CHANGELOG.md
index dd05e25f03..6716500656 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -42,6 +42,7 @@
 - **fix(translator): inject a placeholder message when the Responses API `input[]` is empty** — a `POST /v1/responses` with `input: []` translated to `messages: []`, which every upstream Chat-Completions provider rejects (surfaced as a confusing 406); a single placeholder user message is now injected, mirroring the existing empty-string handling. ([#4393](https://github.com/diegosouzapw/OmniRoute/pull/4393) — thanks @diegosouzapw)
 - **fix(providers): serve the api.airforce live `/models` catalog instead of the stale seed** — the api.airforce provider listed a stale hard-coded seed; it now serves the upstream live `/models` catalog. ([#4395](https://github.com/diegosouzapw/OmniRoute/pull/4395) — thanks @diegosouzapw)
 - **fix(cli): non-interactive-safe prompts + `context` alias** — the CLI's `confirm()`/prompt helpers no longer hang in non-interactive (piped/CI) contexts, and a singular `context` alias is accepted alongside `contexts`; the contexts workflow is documented. ([#4439](https://github.com/diegosouzapw/OmniRoute/pull/4439), [#4397](https://github.com/diegosouzapw/OmniRoute/pull/4397) — thanks @diegosouzapw)
+- **fix(cli): `omniroute update` no longer reports a stale "latest" version from npm's cache** — `getLatestVersion()` ran `npm view omniroute version` without `--prefer-online`, so npm could serve a cached value from its HTTP cache and tell users on an older build (e.g. 3.8.30) they were already "running the latest version" even after a newer one (3.8.31) was published. The version check now passes `--prefer-online` to force npm to revalidate against the registry. ([#4376](https://github.com/diegosouzapw/OmniRoute/issues/4376) — thanks @akbardwi)
 - **fix(sse): `web_search_20250305` no longer 400s on MiniMax's Anthropic-compatible endpoint** — PR #2960 added a Claude→Claude bypass that forwards Anthropic's typed server tool `web_search_20250305` untouched, assuming the Claude-format upstream implements Anthropic server tools. MiniMax's `/anthropic` endpoint does not, so `claude → minimax` requests carrying that tool got `HTTP 400 "invalid params, function name or parameters is empty (2013)"`. `supportsNativeWebSearchFallbackBypass` now consults the (already-plumbed) `provider` and excludes providers known not to implement server tools (currently `minimax`) from the bypass, so the built-in web-search tool is converted to the `omniroute_web_search` function fallback — which MiniMax accepts as a normal function tool. ([#4481](https://github.com/diegosouzapw/OmniRoute/issues/4481) — thanks @shafqatevo)
 
 ### 🔒 Security
diff --git a/bin/cli/commands/update.mjs b/bin/cli/commands/update.mjs
index f5c696e09d..443f9a498b 100644
--- a/bin/cli/commands/update.mjs
+++ b/bin/cli/commands/update.mjs
@@ -25,9 +25,13 @@ export async function getCurrentVersion() {
   }
 }
 
-async function getLatestVersion() {
+// `--prefer-online` forces npm to revalidate its HTTP cache against the registry.
+// Without it `npm view` can return a stale cached version (e.g. report 3.8.30 as
+// "latest" after 3.8.31 was published), so the updater told users on an old build
+// they were already on the latest version (#4376). `execFn` is injectable for tests.
+export async function getLatestVersion(execFn = execFileAsync) {
   try {
-    const { stdout } = await execFileAsync("npm", ["view", "omniroute", "version"], {
+    const { stdout } = await execFn("npm", ["view", "omniroute", "version", "--prefer-online"], {
       timeout: 15000,
     });
     return stdout.trim();
diff --git a/tests/unit/cli-update-prefer-online-4376.test.ts b/tests/unit/cli-update-prefer-online-4376.test.ts
new file mode 100644
index 0000000000..40cd54474c
--- /dev/null
+++ b/tests/unit/cli-update-prefer-online-4376.test.ts
@@ -0,0 +1,36 @@
+import test from "node:test";
+import assert from "node:assert/strict";
+
+const update = await import("../../bin/cli/commands/update.mjs");
+
+// #4376: `omniroute update` reported "Latest version: 3.8.30" while npm's `latest`
+// dist-tag was already 3.8.31, so it told users on an old build they were "running
+// the latest version". Root cause: getLatestVersion() ran `npm view omniroute version`
+// without `--prefer-online`, so npm served a stale value from its HTTP cache.
+// The fix forces npm to revalidate the cache against the registry.
+test("getLatestVersion passes --prefer-online to bypass the stale npm cache (#4376)", async () => {
+  let capturedArgs = null;
+  const fakeExec = async (cmd: string, args: string[]) => {
+    capturedArgs = { cmd, args };
+    return { stdout: "3.8.31\n" };
+  };
+  const latest = await update.getLatestVersion(fakeExec);
+  assert.equal(latest, "3.8.31");
+  assert.ok(capturedArgs, "exec must be invoked");
+  assert.equal(capturedArgs.cmd, "npm");
+  assert.ok(
+    capturedArgs.args.includes("--prefer-online"),
+    `expected --prefer-online in npm args, got: ${JSON.stringify(capturedArgs.args)}`
+  );
+  // still the right query
+  assert.ok(capturedArgs.args.includes("view"));
+  assert.ok(capturedArgs.args.includes("omniroute"));
+  assert.ok(capturedArgs.args.includes("version"));
+});
+
+test("getLatestVersion returns null when npm is unavailable (#4376)", async () => {
+  const latest = await update.getLatestVersion(async () => {
+    throw new Error("npm not found");
+  });
+  assert.equal(latest, null);
+});