diff --git a/package-lock.json b/package-lock.json
index 5823b09a78..3fdfc93723 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -26652,6 +26652,7 @@
         "@types/mkdirp": "^1.0.2",
         "@types/mocha": "^8.2.3",
         "@types/node": "^14.18.63",
+        "@types/semver": "^7.5.8",
         "@types/sinon": "^10.0.20",
         "chai": "^4.5.0",
         "eslint": "^8.57.1",
diff --git a/packages/contentstack/package.json b/packages/contentstack/package.json
index 3e43bc1d0c..22c8e7ff6a 100755
--- a/packages/contentstack/package.json
+++ b/packages/contentstack/package.json
@@ -61,6 +61,7 @@
     "@types/mkdirp": "^1.0.2",
     "@types/mocha": "^8.2.3",
     "@types/node": "^14.18.63",
+    "@types/semver": "^7.5.8",
     "@types/sinon": "^10.0.20",
     "chai": "^4.5.0",
     "eslint": "^8.57.1",
@@ -153,7 +154,8 @@
     "hooks": {
       "prerun": [
         "./lib/hooks/prerun/command-deprecation-check",
-        "./lib/hooks/prerun/default-rate-limit-check"
+        "./lib/hooks/prerun/default-rate-limit-check",
+        "./lib/hooks/prerun/latest-version-warning"
       ],
       "init": [
         "./lib/hooks/init/context-init",
diff --git a/packages/contentstack/src/hooks/prerun/latest-version-warning.ts b/packages/contentstack/src/hooks/prerun/latest-version-warning.ts
new file mode 100644
index 0000000000..4bf110faf9
--- /dev/null
+++ b/packages/contentstack/src/hooks/prerun/latest-version-warning.ts
@@ -0,0 +1,60 @@
+import { cliux, configHandler, HttpClient, LoggerService } from '@contentstack/cli-utilities';
+import * as semver from 'semver';
+interface ICacheData {
+  lastChecked: number;
+  lastWarnedDate: string;
+  latestVersion: string;
+}
+interface IVersionUpgradeWarningFrequency {
+  versionSyncDuration: number;
+}
+const versionUpgradeWarningFrequency: IVersionUpgradeWarningFrequency = {
+  versionSyncDuration: 3 * 24 * 60 * 60 * 1000,
+};
+export default async function (_opts): Promise<void> {
+  const now = Date.now();
+  const today = '2023-11-21';
+  let logger!: LoggerService;
+  logger = new LoggerService(process.cwd(), 'cli-log');
+  let cache: ICacheData = { lastChecked: 0, lastWarnedDate: '', latestVersion: '' };
+
+  if (!configHandler.get('versionUpgradeWarningFrequency')) {
+    configHandler.set('versionUpgradeWarningFrequency', versionUpgradeWarningFrequency);
+  }
+  const versionUpgradeWarningFrequencyConfig: IVersionUpgradeWarningFrequency = configHandler.get(
+    'versionUpgradeWarningFrequency',
+  );
+
+  // Load cache if it exists
+  if (configHandler.get('versionUpgradeWarningCache')) {
+    cache = configHandler.get('versionUpgradeWarningCache');
+  }
+
+  // Perform update check if needed
+  const httpClient = new HttpClient();
+
+  if (now - cache.lastChecked > versionUpgradeWarningFrequencyConfig.versionSyncDuration) {
+    try {
+      const latestVersion = (await httpClient.get(`https://registry.npmjs.org/@contentstack/cli/latest`)).data.version;
+      cache.latestVersion = latestVersion;
+      cache.lastChecked = now;
+
+      // Save updated cache
+      configHandler.set('versionUpgradeWarningCache', cache);
+    } catch (error) {
+      logger.error('Failed to check the latest version', error);
+      return;
+    }
+  }
+
+  // Show warning if an update is available and last warning was > 3 hours ago
+  if (semver.gt(cache.latestVersion, this.config.version) && cache.lastWarnedDate !== today) {
+    cliux.print(
+      `You are using version ${this.config.version}, but the latest version is ${cache.latestVersion}. Please update your CLI for the best experience.`,
+      { color: 'yellow' },
+    );
+    // Update the last warned timestamp
+    cache.lastWarnedDate = today;
+    configHandler.set('versionUpgradeWarningCache', cache);
+  }
+}
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 9e0f6e86ef..a3b55f2329 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -38,6 +38,7 @@ importers:
       '@types/mkdirp': ^1.0.2
       '@types/mocha': ^8.2.3
       '@types/node': ^14.18.63
+      '@types/semver': ^7.5.8
       '@types/sinon': ^10.0.20
       chai: ^4.5.0
       chalk: ^4.1.2
@@ -103,6 +104,7 @@ importers:
       '@types/mkdirp': 1.0.2
       '@types/mocha': 8.2.3
       '@types/node': 14.18.63
+      '@types/semver': 7.5.8
       '@types/sinon': 10.0.20
       chai: 4.5.0
       eslint: 8.57.1