diff --git a/packages/aws-cdk/lib/cli/util/npm.ts b/packages/aws-cdk/lib/cli/util/npm.ts
index 02887503d..9f8434f36 100644
--- a/packages/aws-cdk/lib/cli/util/npm.ts
+++ b/packages/aws-cdk/lib/cli/util/npm.ts
@@ -1,22 +1,34 @@
 import { exec as _exec } from 'child_process';
 import { promisify } from 'util';
-import * as semver from 'semver';
 import { ToolkitError } from '../../../../@aws-cdk/tmp-toolkit-helpers/src/api';
-import { debug } from '../../logging';
 
 const exec = promisify(_exec);
 
-/* c8 ignore start */ // not called during unit tests
-export async function getLatestVersionFromNpm(): Promise<string> {
-  const { stdout, stderr } = await exec('npm view aws-cdk version', { timeout: 3000 });
-  if (stderr && stderr.trim().length > 0) {
-    debug(`The 'npm view' command generated an error stream with content [${stderr.trim()}]`);
-  }
-  const latestVersion = stdout.trim();
-  if (!semver.valid(latestVersion)) {
-    throw new ToolkitError(`npm returned an invalid semver ${latestVersion}`);
-  }
+/* c8 ignore start */
+export async function execNpmView(currentVersion: string) {
+  try {
+    // eslint-disable-next-line @cdklabs/promiseall-no-unbounded-parallelism
+    const [latestResult, currentResult] = await Promise.all([
+      exec('npm view aws-cdk@latest version', { timeout: 3000 }),
+      exec(`npm view aws-cdk@${currentVersion} name version deprecated --json`, { timeout: 3000 }),
+    ]);
+
+    if (latestResult.stderr && latestResult.stderr.trim().length > 0) {
+      throw new ToolkitError(`npm view command for latest version failed: ${latestResult.stderr.trim()}`);
+    }
+    if (currentResult.stderr && currentResult.stderr.trim().length > 0) {
+      throw new ToolkitError(`npm view command for current version failed: ${currentResult.stderr.trim()}`);
+    }
 
-  return latestVersion;
+    const latestVersion = latestResult.stdout;
+    const currentInfo = JSON.parse(currentResult.stdout);
+
+    return {
+      latestVersion: latestVersion,
+      deprecated: currentInfo.deprecated,
+    };
+  } catch (err: unknown) {
+    throw err;
+  }
 }
 /* c8 ignore stop */
diff --git a/packages/aws-cdk/lib/cli/version.ts b/packages/aws-cdk/lib/cli/version.ts
index 66e65a397..e23320384 100644
--- a/packages/aws-cdk/lib/cli/version.ts
+++ b/packages/aws-cdk/lib/cli/version.ts
@@ -8,7 +8,7 @@ import { debug, info } from '../logging';
 import { cdkCacheDir } from '../util';
 import { cliRootDir } from './root-dir';
 import { formatAsBanner } from './util/console-formatters';
-import { getLatestVersionFromNpm } from './util/npm';
+import { execNpmView } from './util/npm';
 
 const ONE_DAY_IN_SECONDS = 1 * 24 * 60 * 60;
 
@@ -84,20 +84,28 @@ export class VersionCheckTTL {
 
 // Export for unit testing only.
 // Don't use directly, use displayVersionMessage() instead.
-export async function latestVersionIfHigher(currentVersion: string, cacheFile: VersionCheckTTL): Promise<string|null> {
+export async function getVersionMessages(currentVersion: string, cacheFile: VersionCheckTTL): Promise<string[]> {
   if (!(await cacheFile.hasExpired())) {
-    return null;
+    return [];
   }
 
-  const latestVersion = await getLatestVersionFromNpm();
-  const isNewer = semver.gt(latestVersion, currentVersion);
-  await cacheFile.update(latestVersion);
+  const packageInfo = await execNpmView(currentVersion);
+  const latestVersion = packageInfo.latestVersion;
+  await cacheFile.update(JSON.stringify(packageInfo));
 
-  if (isNewer) {
-    return latestVersion;
-  } else {
-    return null;
+  // If the latest version is the same as the current version, there is no need to display a message
+  if (semver.eq(latestVersion, currentVersion)) {
+    return [];
   }
+
+  const versionMessage = [
+    packageInfo.deprecated ? `${chalk.red(packageInfo.deprecated as string)}` : undefined,
+    `Newer version of CDK is available [${chalk.green(latestVersion as string)}]`,
+    getMajorVersionUpgradeMessage(currentVersion),
+    'Upgrade recommended (npm install -g aws-cdk)',
+  ].filter(Boolean) as string[];
+
+  return versionMessage;
 }
 
 function getMajorVersionUpgradeMessage(currentVersion: string): string | void {
@@ -107,25 +115,14 @@ function getMajorVersionUpgradeMessage(currentVersion: string): string | void {
   }
 }
 
-function getVersionMessage(currentVersion: string, laterVersion: string): string[] {
-  return [
-    `Newer version of CDK is available [${chalk.green(laterVersion as string)}]`,
-    getMajorVersionUpgradeMessage(currentVersion),
-    'Upgrade recommended (npm install -g aws-cdk)',
-  ].filter(Boolean) as string[];
-}
-
 export async function displayVersionMessage(currentVersion = versionNumber(), versionCheckCache?: VersionCheckTTL): Promise<void> {
   if (!process.stdout.isTTY || process.env.CDK_DISABLE_VERSION_CHECK) {
     return;
   }
 
   try {
-    const laterVersion = await latestVersionIfHigher(currentVersion, versionCheckCache ?? new VersionCheckTTL());
-    if (laterVersion) {
-      const bannerMsg = formatAsBanner(getVersionMessage(currentVersion, laterVersion));
-      bannerMsg.forEach((e) => info(e));
-    }
+    const versionMessages = await getVersionMessages(currentVersion, versionCheckCache ?? new VersionCheckTTL());
+    formatAsBanner(versionMessages).forEach(e => info(e));
   } catch (err: any) {
     debug(`Could not run version check - ${err.message}`);
   }
diff --git a/packages/aws-cdk/lib/legacy-exports-source.ts b/packages/aws-cdk/lib/legacy-exports-source.ts
index 45cc81224..0c21809b7 100644
--- a/packages/aws-cdk/lib/legacy-exports-source.ts
+++ b/packages/aws-cdk/lib/legacy-exports-source.ts
@@ -24,7 +24,7 @@ export { cli, exec } from './cli/cli';
 export { cliRootDir as rootDir } from './cli/root-dir';
 export { Command, Configuration, PROJECT_CONTEXT } from './cli/user-configuration';
 export { formatAsBanner } from './cli/util/console-formatters';
-export { latestVersionIfHigher, versionNumber } from './cli/version';
+export { versionNumber } from './cli/version';
 
 // Commands
 export { RequireApproval } from './commands/diff';
diff --git a/packages/aws-cdk/lib/legacy-exports.ts b/packages/aws-cdk/lib/legacy-exports.ts
index 9ca2731b6..1eb2572de 100644
--- a/packages/aws-cdk/lib/legacy-exports.ts
+++ b/packages/aws-cdk/lib/legacy-exports.ts
@@ -65,7 +65,6 @@ export const {
   deepMerge,
   Deployments,
   rootDir,
-  latestVersionIfHigher,
   versionNumber,
   availableInitTemplates,
   cached,
diff --git a/packages/aws-cdk/test/cli/version.test.ts b/packages/aws-cdk/test/cli/version.test.ts
index a13d945a0..bd6a1512a 100644
--- a/packages/aws-cdk/test/cli/version.test.ts
+++ b/packages/aws-cdk/test/cli/version.test.ts
@@ -1,16 +1,17 @@
 /* eslint-disable import/order */
-import * as path from 'path';
-import { setTimeout as _setTimeout } from 'timers';
-import { promisify } from 'util';
 import * as fs from 'fs-extra';
 import * as os from 'os';
+import * as path from 'path';
 import * as sinon from 'sinon';
-import * as logging from '../../lib/logging';
+import { setTimeout as _setTimeout } from 'timers';
+import { promisify } from 'util';
 import * as npm from '../../lib/cli/util/npm';
-import { latestVersionIfHigher, VersionCheckTTL, displayVersionMessage, isDeveloperBuild } from '../../lib/cli/version';
+import { displayVersionMessage, getVersionMessages, isDeveloperBuild, VersionCheckTTL } from '../../lib/cli/version';
+import * as logging from '../../lib/logging';
 
 jest.setTimeout(10_000);
 
+
 const setTimeout = promisify(_setTimeout);
 
 function tmpfile(): string {
@@ -18,7 +19,6 @@ function tmpfile(): string {
 }
 
 beforeEach(() => {
-  jest.spyOn(npm, 'getLatestVersionFromNpm').mockRejectedValue(new Error('expected version cache to be used, but call to npm was attempted'));
   process.chdir(os.tmpdir()); // Need a chdir because in the workspace 'npm view' will take a long time
 });
 
@@ -49,25 +49,7 @@ test('cache file honours the specified TTL', async () => {
 test('Skip version check if cache has not expired', async () => {
   const cache = new VersionCheckTTL(tmpfile(), 100);
   await cache.update();
-  expect(await latestVersionIfHigher('0.0.0', cache)).toBeNull();
-});
-
-test('Return later version when exists & skip recent re-check', async () => {
-  const cache = new VersionCheckTTL(tmpfile(), 100);
-  jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValueOnce('1.1.0');
-  const result = await latestVersionIfHigher('0.0.0', cache);
-  expect(result).not.toBeNull();
-  expect((result as string).length).toBeGreaterThan(0);
-
-  const result2 = await latestVersionIfHigher('0.0.0', cache);
-  expect(result2).toBeNull();
-});
-
-test('Return null if version is higher than npm', async () => {
-  const cache = new VersionCheckTTL(tmpfile(), 100);
-  jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValueOnce('1.1.0');
-  const result = await latestVersionIfHigher('100.100.100', cache);
-  expect(result).toBeNull();
+  expect(await getVersionMessages('0.0.0', cache)).toEqual([]);
 });
 
 test('Version specified is stored in the TTL file', async () => {
@@ -104,45 +86,62 @@ describe('version message', () => {
     process.stdout.isTTY = previousIsTty;
   });
 
-  test('Prints a message when a new version is available', async () => {
-    // Given the current version is 1.0.0 and the latest version is 1.1.0
-    const currentVersion = '1.0.0';
-    jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValueOnce('1.1.0');
-    const printSpy = jest.spyOn(logging, 'info');
-
-    // When displayVersionMessage is called
-    await displayVersionMessage(currentVersion, new VersionCheckTTL(tmpfile(), 0));
-
-    // Then the new version message is printed to stdout
-    expect(printSpy).toHaveBeenCalledWith(expect.stringContaining('1.1.0'));
-  });
-
-  test('Includes major upgrade documentation when available', async() => {
-    // Given the current version is 1.0.0 and the latest version is 2.0.0
-    const currentVersion = '1.0.0';
-    jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValueOnce('2.0.0');
-    const printSpy = jest.spyOn(logging, 'info');
-
-    // When displayVersionMessage is called
-    await displayVersionMessage(currentVersion, new VersionCheckTTL(tmpfile(), 0));
-
-    // Then the V1 -> V2 documentation is printed
-    expect(printSpy).toHaveBeenCalledWith(expect.stringContaining('Information about upgrading from version 1.x to version 2.x is available here: https://docs.aws.amazon.com/cdk/v2/guide/migrating-v2.html'));
-  });
-
-  test('Does not include major upgrade documentation when unavailable', async() => {
-    // Given current version is 99.0.0 and the latest version is 100.0.0
-    const currentVersion = '99.0.0';
-    jest.spyOn(npm, 'getLatestVersionFromNpm').mockResolvedValueOnce('100.0.0');
-    const printSpy = jest.spyOn(logging, 'info');
-
-    // When displayVersionMessage is called
-    await displayVersionMessage(currentVersion, new VersionCheckTTL(tmpfile(), 0));
-
-    // Then no upgrade documentation is printed
-    expect(printSpy).toHaveBeenCalledWith(expect.stringContaining('100.0.0'));
-    expect(printSpy).not.toHaveBeenCalledWith(expect.stringContaining('Information about upgrading from 99.x to 100.x'));
-  });
+  test('Prints messages when a new version is available', async () => {
+    const mockCache = new VersionCheckTTL(tmpfile());
+    jest.spyOn(mockCache, 'hasExpired').mockResolvedValue(true);
+    
+    jest.spyOn(npm, 'execNpmView').mockResolvedValue({
+      latestVersion: '2.0.0',
+      deprecated: undefined,
+    });
+    
+    const messages = await getVersionMessages('1.0.0', mockCache);
+    expect(messages.some(msg => msg.includes('Newer version of CDK is available'))).toBeTruthy();
+    expect(messages.some(msg => msg.includes('Information about upgrading from version 1.x to version 2.x'))).toBeTruthy();
+    expect(messages.some(msg => msg.includes('Upgrade recommended (npm install -g aws-cdk)'))).toBeTruthy();
+  })
+  
+  test('Does not include major upgrade documentation when unavailable', async () => {
+    const mockCache = new VersionCheckTTL(tmpfile());
+    jest.spyOn(mockCache, 'hasExpired').mockResolvedValue(true);
+    
+    jest.spyOn(npm, 'execNpmView').mockResolvedValue({
+      latestVersion: '2.1000.0',
+      deprecated: undefined,
+    });
+    
+    const messages = await getVersionMessages('2.179.0', mockCache);
+    const hasUpgradeDoc = messages.some(msg => 
+      msg.includes('Information about upgrading from version 1.x to version 2.x')
+    );
+    expect(hasUpgradeDoc).toBeFalsy();
+  })
+  
+  test('Prints a message when a deprecated version is used', async () => {
+    const mockCache = new VersionCheckTTL(tmpfile());
+    jest.spyOn(mockCache, 'hasExpired').mockResolvedValue(true);
+    
+    jest.spyOn(npm, 'execNpmView').mockResolvedValue({
+      latestVersion: '2.0.0',
+      deprecated: 'This version is deprecated.',
+    });
+    
+    const messages = await getVersionMessages('1.0.0', mockCache);
+    expect(messages.some(msg => msg.includes('This version is deprecated'))).toBeTruthy();
+  })
+  
+  test('Does not print message when current version is up to date', async () => {
+    const mockCache = new VersionCheckTTL(tmpfile());
+    jest.spyOn(mockCache, 'hasExpired').mockResolvedValue(true);
+    
+    jest.spyOn(npm, 'execNpmView').mockResolvedValue({
+      latestVersion: '1.0.0',
+      deprecated: undefined,
+    });
+    
+    const messages = await getVersionMessages('1.0.0', mockCache);
+    expect(messages).toEqual([]);
+  })
 });
 
 test('isDeveloperBuild call does not throw an error', () => {