diff --git a/.changeset/thick-glasses-lick.md b/.changeset/thick-glasses-lick.md
new file mode 100644
index 0000000000..2f6d8e7794
--- /dev/null
+++ b/.changeset/thick-glasses-lick.md
@@ -0,0 +1,5 @@
+---
+'@sap-cloud-sdk/connectivity': minor
+---
+
+[Fixed Issue] Check `Proxy-Authorization` and `SAP-Connectivity-Authentication` tokens to determine cache expiration time.
diff --git a/packages/connectivity/src/scp-cf/destination/destination-cache.spec.ts b/packages/connectivity/src/scp-cf/destination/destination-cache.spec.ts
index a6c39f8bd8..7e559eb847 100644
--- a/packages/connectivity/src/scp-cf/destination/destination-cache.spec.ts
+++ b/packages/connectivity/src/scp-cf/destination/destination-cache.spec.ts
@@ -31,6 +31,7 @@ import {
   mockJwtBearerToken,
   mockServiceToken
 } from '../../../../../test-resources/test/test-util/token-accessor-mocks';
+import { signedJwtForVerification } from '../../../../../test-resources/test/test-util';
 import { destinationServiceCache } from './destination-service-cache';
 import {
   alwaysProvider,
@@ -806,6 +807,112 @@ describe('destination cache', () => {
     });
   });
 
+  it('should return undefined when Proxy-Authorization token expires first', async () => {
+    jest.useFakeTimers();
+    const twoMinutesTokenLifetime = 2 * 60;
+    const fourMinutesTokenLifetime = 4 * 60;
+    const sixMinutesTokenLifetime = 6 * 60;
+    const dummyJwt = { user_id: 'user', zid: 'tenant' };
+
+    const proxyAuthorizationToken = signedJwtForVerification({
+      ...decodeJwt(providerServiceToken),
+      exp: twoMinutesTokenLifetime
+    });
+
+    const sapConnectivityAuthenticationToken = signedJwtForVerification({
+      ...decodeJwt(providerUserToken),
+      exp: fourMinutesTokenLifetime
+    });
+
+    const destination = {
+      ...destinationOne,
+      authTokens: [
+        {
+          expiresIn: sixMinutesTokenLifetime.toString()
+        } as DestinationAuthToken
+      ],
+      proxyConfiguration: {
+        ...connectivityProxyConfigMock,
+        headers: {
+          'Proxy-Authorization': `Bearer ${proxyAuthorizationToken}`,
+          'SAP-Connectivity-Authentication': `Bearer ${sapConnectivityAuthenticationToken}`
+        }
+      }
+    };
+
+    await destinationCache.cacheRetrievedDestination(
+      dummyJwt,
+      destination,
+      'tenant-user'
+    );
+
+    const retrieveDestination = () =>
+      destinationCache.retrieveDestinationFromCache(
+        dummyJwt,
+        destination.name!,
+        'tenant-user'
+      );
+
+    await expect(retrieveDestination()).resolves.toEqual(destination);
+
+    jest.advanceTimersByTime(twoMinutesTokenLifetime * 1000 + 1);
+
+    await expect(retrieveDestination()).resolves.toBeUndefined();
+  });
+
+  it('should return undefined when SAP-Connectivity-Authentication authorization token expires first', async () => {
+    jest.useFakeTimers();
+    const twoMinutesTokenLifetime = 2 * 60;
+    const fourMinutesTokenLifetime = 4 * 60;
+    const sixMinutesTokenLifetime = 6 * 60;
+    const dummyJwt = { user_id: 'user', zid: 'tenant' };
+
+    const proxyAuthorizationToken = signedJwtForVerification({
+      ...decodeJwt(providerServiceToken),
+      exp: fourMinutesTokenLifetime
+    });
+
+    const sapConnectivityAuthenticationToken = signedJwtForVerification({
+      ...decodeJwt(providerUserToken),
+      exp: twoMinutesTokenLifetime
+    });
+
+    const destination = {
+      ...destinationOne,
+      authTokens: [
+        {
+          expiresIn: sixMinutesTokenLifetime.toString()
+        } as DestinationAuthToken
+      ],
+      proxyConfiguration: {
+        ...connectivityProxyConfigMock,
+        headers: {
+          'Proxy-Authorization': `Bearer ${proxyAuthorizationToken}`,
+          'SAP-Connectivity-Authentication': `Bearer ${sapConnectivityAuthenticationToken}`
+        }
+      }
+    };
+
+    await destinationCache.cacheRetrievedDestination(
+      dummyJwt,
+      destination,
+      'tenant-user'
+    );
+
+    const retrieveDestination = () =>
+      destinationCache.retrieveDestinationFromCache(
+        dummyJwt,
+        destination.name!,
+        'tenant-user'
+      );
+
+    await expect(retrieveDestination()).resolves.toEqual(destination);
+
+    jest.advanceTimersByTime(twoMinutesTokenLifetime * 1000 + 1);
+
+    await expect(retrieveDestination()).resolves.toBeUndefined();
+  });
+
   describe('custom destination cache', () => {
     // Cache with expiration time
     const testCacheOne = new TestCache();
diff --git a/packages/connectivity/src/scp-cf/destination/destination-cache.ts b/packages/connectivity/src/scp-cf/destination/destination-cache.ts
index 5a055e7b56..94d9372c9e 100644
--- a/packages/connectivity/src/scp-cf/destination/destination-cache.ts
+++ b/packages/connectivity/src/scp-cf/destination/destination-cache.ts
@@ -1,5 +1,5 @@
 import { createLogger, first } from '@sap-cloud-sdk/util';
-import { getTenantId, userId } from '../jwt';
+import { decodeJwt, getTenantId, userId } from '../jwt';
 import { AsyncCache } from '../async-cache';
 import type { JwtPayload } from '../jsonwebtoken-type';
 import type { AsyncCacheInterface } from '../async-cache';
@@ -217,11 +217,40 @@ async function cacheRetrievedDestination<T extends DestinationCacheInterface>(
     throw new Error('The destination name is undefined.');
   }
 
-  const key = getDestinationCacheKey(token, destination.name, isolation);
-  const expiresIn = first(destination.authTokens || [])?.expiresIn;
-  const expirationTime = expiresIn
-    ? Date.now() + parseInt(expiresIn) * 1000
+  const authToken = first(destination.authTokens || []);
+  const proxyAuthorizationToken =
+    destination.proxyConfiguration?.headers?.['Proxy-Authorization']?.match(
+      /^Bearer (.+)/
+    )?.[1];
+  const sapConnectivityAuthenticationToken =
+    destination.proxyConfiguration?.headers?.[
+      'SAP-Connectivity-Authentication'
+    ]?.match(/^Bearer (.+)/)?.[1];
+
+  const authTokenExpiresIn = authToken?.expiresIn
+    ? parseInt(authToken.expiresIn)
     : undefined;
+  const proxyAuthorizationExpiresIn = proxyAuthorizationToken
+    ? decodeJwt(proxyAuthorizationToken).exp
+    : undefined;
+  const sapConnectivityAuthenticationExpiresIn =
+    sapConnectivityAuthenticationToken
+      ? decodeJwt(sapConnectivityAuthenticationToken).exp
+      : undefined;
+
+  const expiresIn = Math.min(
+    ...[
+      authTokenExpiresIn,
+      proxyAuthorizationExpiresIn,
+      sapConnectivityAuthenticationExpiresIn
+    ].filter(e => e !== undefined)
+  );
+  const expirationTime =
+    expiresIn && expiresIn !== Infinity
+      ? Date.now() + expiresIn * 1000
+      : undefined;
+
+  const key = getDestinationCacheKey(token, destination.name, isolation);
   cache.set(key, { entry: destination, expires: expirationTime });
 }