diff --git a/packages/cli/src/__tests__/license.test.ts b/packages/cli/src/__tests__/license.test.ts
index 0e26d0d81c513..fb82f312ee641 100644
--- a/packages/cli/src/__tests__/license.test.ts
+++ b/packages/cli/src/__tests__/license.test.ts
@@ -16,6 +16,12 @@ const MOCK_ACTIVATION_KEY = 'activation-key';
 const MOCK_FEATURE_FLAG = 'feat:sharing';
 const MOCK_MAIN_PLAN_ID = '1b765dc4-d39d-4ffe-9885-c56dd67c4b26';
 
+function makeDateWithHourOffset(offsetInHours: number): Date {
+	const date = new Date();
+	date.setHours(date.getHours() + offsetInHours);
+	return date;
+}
+
 const licenseConfig: GlobalConfig['license'] = {
 	serverUrl: MOCK_SERVER_URL,
 	autoRenewalEnabled: true,
@@ -134,7 +140,7 @@ describe('License', () => {
 		expect(LicenseManager.prototype.getManagementJwt).toHaveBeenCalled();
 	});
 
-	test('getMainPlan() returns the right entitlement', async () => {
+	test('getMainPlan() returns the latest main entitlement', async () => {
 		// mock entitlements response
 		License.prototype.getCurrentEntitlements = jest.fn().mockReturnValue([
 			{
@@ -143,8 +149,21 @@ describe('License', () => {
 				productMetadata: {},
 				features: {},
 				featureOverrides: {},
-				validFrom: new Date(),
-				validTo: new Date(),
+				validFrom: makeDateWithHourOffset(-3),
+				validTo: makeDateWithHourOffset(1),
+			},
+			{
+				id: '95b9c852-1349-478d-9ad1-b3f55510e488',
+				productId: '670650f2-72d8-4397-898c-c249906e2cc2',
+				productMetadata: {
+					terms: {
+						isMainPlan: true,
+					},
+				},
+				features: {},
+				featureOverrides: {},
+				validFrom: makeDateWithHourOffset(-2),
+				validTo: makeDateWithHourOffset(1),
 			},
 			{
 				id: MOCK_MAIN_PLAN_ID,
@@ -156,8 +175,8 @@ describe('License', () => {
 				},
 				features: {},
 				featureOverrides: {},
-				validFrom: new Date(),
-				validTo: new Date(),
+				validFrom: makeDateWithHourOffset(-1), // this is the LATEST / newest plan
+				validTo: makeDateWithHourOffset(1),
 			},
 		]);
 		jest.fn(license.getMainPlan).mockReset();
@@ -175,8 +194,8 @@ describe('License', () => {
 				productMetadata: {}, // has no `productMetadata.terms.isMainPlan`!
 				features: {},
 				featureOverrides: {},
-				validFrom: new Date(),
-				validTo: new Date(),
+				validFrom: makeDateWithHourOffset(-1),
+				validTo: makeDateWithHourOffset(1),
 			},
 			{
 				id: 'c1aae471-c24e-4874-ad88-b97107de486c',
@@ -184,8 +203,8 @@ describe('License', () => {
 				productMetadata: {}, // has no `productMetadata.terms.isMainPlan`!
 				features: {},
 				featureOverrides: {},
-				validFrom: new Date(),
-				validTo: new Date(),
+				validFrom: makeDateWithHourOffset(-1),
+				validTo: makeDateWithHourOffset(1),
 			},
 		]);
 		jest.fn(license.getMainPlan).mockReset();
diff --git a/packages/cli/src/license.ts b/packages/cli/src/license.ts
index 0b02e7da1a79c..7e1a443495120 100644
--- a/packages/cli/src/license.ts
+++ b/packages/cli/src/license.ts
@@ -330,7 +330,7 @@ export class License {
 	}
 
 	/**
-	 * Helper function to get the main plan for a license
+	 * Helper function to get the latest main plan for a license
 	 */
 	getMainPlan(): TEntitlement | undefined {
 		if (!this.manager) {
@@ -342,6 +342,8 @@ export class License {
 			return undefined;
 		}
 
+		entitlements.sort((a, b) => b.validFrom.getTime() - a.validFrom.getTime());
+
 		return entitlements.find(
 			(entitlement) => (entitlement.productMetadata?.terms as { isMainPlan?: boolean })?.isMainPlan,
 		);