diff --git a/src/infra/update-global.ts b/src/infra/update-global.ts
index 42e3fd7b980..dedff0b9d53 100644
--- a/src/infra/update-global.ts
+++ b/src/infra/update-global.ts
@@ -13,7 +13,7 @@ import {
 } from "./package-dist-inventory.js";
 import { readPackageVersion } from "./package-json.js";
 import { applyPathPrepend } from "./path-prepend.js";
-import { isAtLeast, parseSemver } from "./runtime-guard.js";
+import { parseSemver } from "./runtime-guard.js";
 
 export type GlobalInstallManager = "npm" | "pnpm" | "bun";
 
@@ -108,7 +108,17 @@ export async function collectInstalledGlobalPackageErrors(params: {
 }
 
 function shouldRequirePackagedDistInventory(version: string | null | undefined): boolean {
-  return isAtLeast(parseSemver(version ?? null), FIRST_PACKAGED_DIST_INVENTORY_VERSION);
+  const parsed = parseSemver(version ?? null);
+  if (!parsed) {
+    return false;
+  }
+  if (parsed.major !== FIRST_PACKAGED_DIST_INVENTORY_VERSION.major) {
+    return parsed.major > FIRST_PACKAGED_DIST_INVENTORY_VERSION.major;
+  }
+  if (parsed.minor !== FIRST_PACKAGED_DIST_INVENTORY_VERSION.minor) {
+    return parsed.minor > FIRST_PACKAGED_DIST_INVENTORY_VERSION.minor;
+  }
+  return parsed.patch >= FIRST_PACKAGED_DIST_INVENTORY_VERSION.patch;
 }
 
 async function collectInstalledPackageDistErrors(params: {
@@ -116,7 +126,7 @@ async function collectInstalledPackageDistErrors(params: {
   installedVersion: string | null;
   expectedVersion?: string | null;
 }): Promise<string[]> {
-  const criticalPaths = await collectLegacyInstalledPackageDistPaths(params.packageRoot);
+  const criticalPaths = await collectCriticalInstalledPackageDistPaths(params.packageRoot);
   let inventoryFiles: string[] | null = null;
   let inventoryError: string | null = null;
   try {
@@ -154,7 +164,7 @@ async function collectInstalledPackageDistErrors(params: {
 
   const criticalErrors = await collectInstalledPathErrors({
     packageRoot: params.packageRoot,
-    expectedFiles: criticalPaths,
+    expectedFiles: await collectLegacyInstalledPackageDistPaths(params.packageRoot),
     actualFiles: null,
     missingMessage: (relativePath) => `missing bundled runtime sidecar ${relativePath}`,
   });
@@ -175,8 +185,19 @@ async function collectInstalledPackageDistErrors(params: {
 
 async function collectLegacyInstalledPackageDistPaths(packageRoot: string): Promise<string[]> {
   const expectedFiles = new Set(NPM_UPDATE_COMPAT_SIDECAR_PATHS);
+  for (const relativePath of await collectCriticalInstalledPackageDistPaths(packageRoot)) {
+    expectedFiles.add(relativePath);
+  }
+  return [...expectedFiles].toSorted((left, right) => left.localeCompare(right));
+}
+
+async function collectCriticalInstalledPackageDistPaths(packageRoot: string): Promise<string[]> {
+  const expectedFiles = new Set<string>();
   await Promise.all(
     BUNDLED_RUNTIME_SIDECAR_PATHS.map(async (relativePath) => {
+      if (NPM_UPDATE_COMPAT_SIDECAR_PATHS.has(relativePath)) {
+        return;
+      }
       const pluginRoot = resolveBundledPluginRoot(relativePath);
       if (pluginRoot === null) {
         return;