diff --git a/src/support/slack/actions/entitlement-modal-utils.js b/src/support/slack/actions/entitlement-modal-utils.js
index 6fdeae8cb..4423f067a 100644
--- a/src/support/slack/actions/entitlement-modal-utils.js
+++ b/src/support/slack/actions/entitlement-modal-utils.js
@@ -168,7 +168,9 @@ export async function updateMessageToProcessing(client, channelId, messageTs, ba
 }
 
 /**
- * Creates entitlements for selected products in parallel
+ * Creates entitlements for selected products in parallel.
+ * If the org already has an entitlement for a product, preserves the existing tier
+ * and only creates the site enrollment if missing.
  * @param {object} lambdaContext - Lambda context
  * @param {object} site - Site object
  * @param {string[]} selectedProducts - Array of product codes
@@ -177,6 +179,36 @@ export async function updateMessageToProcessing(client, channelId, messageTs, ba
 export async function createEntitlementsForProducts(lambdaContext, site, selectedProducts) {
   const entitlementPromises = selectedProducts.map(async (product) => {
     const tierClient = await TierClient.createForSite(lambdaContext, site, product);
+    const existing = await tierClient.checkValidEntitlement();
+
+    if (existing.entitlement) {
+      const currentTier = existing.entitlement.getTier();
+
+      if (existing.siteEnrollment) {
+        return {
+          product,
+          entitlementId: existing.entitlement.getId(),
+          enrollmentId: existing.siteEnrollment.getId(),
+          existingTier: currentTier,
+          alreadyExisted: true,
+        };
+      }
+
+      const { SiteEnrollment } = lambdaContext.dataAccess;
+      const siteEnrollment = await SiteEnrollment.create({
+        siteId: site.getId(),
+        entitlementId: existing.entitlement.getId(),
+      });
+
+      return {
+        product,
+        entitlementId: existing.entitlement.getId(),
+        enrollmentId: siteEnrollment.getId(),
+        existingTier: currentTier,
+        enrollmentCreated: true,
+      };
+    }
+
     const { entitlement, siteEnrollment } = await tierClient.createEntitlement(
       EntitlementModel.TIERS.FREE_TRIAL,
     );
@@ -200,8 +232,17 @@ export async function createEntitlementsForProducts(lambdaContext, site, selecte
 export async function postEntitlementMessages(say, entitlementResults, siteId) {
   /* eslint-disable no-await-in-loop */
   for (const result of entitlementResults) {
-    const message = `:white_check_mark: Ensured ${result.product} entitlement ${result.entitlementId} `
-      + `(${EntitlementModel.TIERS.FREE_TRIAL}) and enrollment ${result.enrollmentId} for site ${siteId}`;
+    let message;
+    if (result.alreadyExisted) {
+      message = `:information_source: ${result.product} entitlement ${result.entitlementId} `
+        + `(${result.existingTier}) and enrollment ${result.enrollmentId} already exist for site ${siteId}`;
+    } else if (result.enrollmentCreated) {
+      message = `:white_check_mark: ${result.product} entitlement ${result.entitlementId} `
+        + `(${result.existingTier}) already existed — created enrollment ${result.enrollmentId} for site ${siteId}`;
+    } else {
+      message = `:white_check_mark: Created ${result.product} entitlement ${result.entitlementId} `
+        + `(${EntitlementModel.TIERS.FREE_TRIAL}) and enrollment ${result.enrollmentId} for site ${siteId}`;
+    }
     await say(message);
   }
   /* eslint-enable no-await-in-loop */
diff --git a/src/support/slack/actions/entitlement-modals.js b/src/support/slack/actions/entitlement-modals.js
index aea911e5a..a73a6490a 100644
--- a/src/support/slack/actions/entitlement-modals.js
+++ b/src/support/slack/actions/entitlement-modals.js
@@ -294,18 +294,31 @@ export function ensureEntitlementImsOrgModal(lambdaContext) {
       for (const product of selectedProducts) {
         try {
           const tierClient = TierClient.createForOrg(lambdaContext, organization, product);
-          const { entitlement } = await tierClient.createEntitlement(
-            EntitlementModel.TIERS.FREE_TRIAL,
-          );
-          entitlementResults.push({
-            product,
-            entitlementId: entitlement.getId(),
-          });
-
-          await say(
-            `:white_check_mark: Ensured ${product} entitlement ${entitlement.getId()} `
-            + `(${EntitlementModel.TIERS.FREE_TRIAL}) for organization ${organizationId}`,
-          );
+          const existing = await tierClient.checkValidEntitlement();
+
+          if (existing.entitlement) {
+            const currentTier = existing.entitlement.getTier();
+            entitlementResults.push({
+              product,
+              entitlementId: existing.entitlement.getId(),
+            });
+            await say(
+              `:information_source: ${product} entitlement ${existing.entitlement.getId()} `
+              + `(${currentTier}) already exists for organization ${organizationId}`,
+            );
+          } else {
+            const { entitlement } = await tierClient.createEntitlement(
+              EntitlementModel.TIERS.FREE_TRIAL,
+            );
+            entitlementResults.push({
+              product,
+              entitlementId: entitlement.getId(),
+            });
+            await say(
+              `:white_check_mark: Created ${product} entitlement ${entitlement.getId()} `
+              + `(${EntitlementModel.TIERS.FREE_TRIAL}) for organization ${organizationId}`,
+            );
+          }
         } catch (error) {
           log.error(`Error creating ${product} entitlement for org ${organizationId}:`, error);
           await say(`:x: Failed to ensure ${product} entitlement: ${error.message}`);
diff --git a/test/support/slack/actions/entitlement-modal-utils.test.js b/test/support/slack/actions/entitlement-modal-utils.test.js
index 3a803e278..423963f81 100644
--- a/test/support/slack/actions/entitlement-modal-utils.test.js
+++ b/test/support/slack/actions/entitlement-modal-utils.test.js
@@ -267,9 +267,9 @@ describe('Modal Utils', () => {
   });
 
   describe('createEntitlementsForProducts', () => {
-    it('creates entitlements for multiple products in parallel', async () => {
+    it('creates new entitlements when none exist', async () => {
       const mockSite = { getId: () => 'site123' };
-      const mockLambdaContext = { env: {}, log: {} };
+      const mockLambdaContext = { env: {}, log: {}, dataAccess: {} };
       const selectedProducts = ['ASO', 'LLMO'];
 
       const mockEntitlement1 = { getId: () => 'entitlement-aso' };
@@ -279,12 +279,14 @@ describe('Modal Utils', () => {
 
       mockTierClient.createForSite
         .onFirstCall().returns({
+          checkValidEntitlement: sinon.stub().resolves({}),
           createEntitlement: sinon.stub().resolves({
             entitlement: mockEntitlement1,
             siteEnrollment: mockEnrollment1,
           }),
         })
         .onSecondCall().returns({
+          checkValidEntitlement: sinon.stub().resolves({}),
           createEntitlement: sinon.stub().resolves({
             entitlement: mockEntitlement2,
             siteEnrollment: mockEnrollment2,
@@ -311,16 +313,16 @@ describe('Modal Utils', () => {
       });
     });
 
-    it('creates entitlement for single product', async () => {
+    it('preserves existing entitlement and returns existing enrollment', async () => {
       const mockSite = { getId: () => 'site456' };
-      const mockLambdaContext = { env: {}, log: {} };
+      const mockLambdaContext = { env: {}, log: {}, dataAccess: {} };
       const selectedProducts = ['ASO'];
 
-      const mockEntitlement = { getId: () => 'entitlement-123' };
-      const mockEnrollment = { getId: () => 'enrollment-123' };
+      const mockEntitlement = { getId: () => 'entitlement-existing', getTier: () => 'PAID' };
+      const mockEnrollment = { getId: () => 'enrollment-existing' };
 
       mockTierClient.createForSite.returns({
-        createEntitlement: sinon.stub().resolves({
+        checkValidEntitlement: sinon.stub().resolves({
           entitlement: mockEntitlement,
           siteEnrollment: mockEnrollment,
         }),
@@ -335,17 +337,60 @@ describe('Modal Utils', () => {
       expect(results).to.have.lengthOf(1);
       expect(results[0]).to.deep.equal({
         product: 'ASO',
-        entitlementId: 'entitlement-123',
-        enrollmentId: 'enrollment-123',
+        entitlementId: 'entitlement-existing',
+        enrollmentId: 'enrollment-existing',
+        existingTier: 'PAID',
+        alreadyExisted: true,
       });
     });
 
-    it('returns empty array for empty product list', async () => {
+    it('creates enrollment when entitlement exists but enrollment does not', async () => {
       const mockSite = { getId: () => 'site789' };
-      const mockLambdaContext = { env: {}, log: {} };
+      const mockEnrollment = { getId: () => 'enrollment-new' };
+      const mockLambdaContext = {
+        env: {},
+        log: {},
+        dataAccess: {
+          SiteEnrollment: {
+            create: sinon.stub().resolves(mockEnrollment),
+          },
+        },
+      };
+      const selectedProducts = ['ASO'];
+
+      const mockEntitlement = { getId: () => 'entitlement-existing', getTier: () => 'PLG' };
+
+      mockTierClient.createForSite.returns({
+        checkValidEntitlement: sinon.stub().resolves({
+          entitlement: mockEntitlement,
+        }),
+      });
+
+      const results = await modalUtils.createEntitlementsForProducts(
+        mockLambdaContext,
+        mockSite,
+        selectedProducts,
+      );
+
+      expect(results).to.have.lengthOf(1);
+      expect(results[0]).to.deep.equal({
+        product: 'ASO',
+        entitlementId: 'entitlement-existing',
+        enrollmentId: 'enrollment-new',
+        existingTier: 'PLG',
+        enrollmentCreated: true,
+      });
+      expect(mockLambdaContext.dataAccess.SiteEnrollment.create).to.have.been.calledWith({
+        siteId: 'site789',
+        entitlementId: 'entitlement-existing',
+      });
+    });
+
+    it('returns empty array for empty product list', async () => {
+      const mockSite = { getId: () => 'site999' };
+      const mockLambdaContext = { env: {}, log: {}, dataAccess: {} };
       const selectedProducts = [];
 
-      // Reset the stub before this test
       mockTierClient.createForSite.resetHistory();
 
       const results = await modalUtils.createEntitlementsForProducts(
@@ -360,7 +405,7 @@ describe('Modal Utils', () => {
   });
 
   describe('postEntitlementMessages', () => {
-    it('posts messages for multiple entitlement results', async () => {
+    it('posts created message for newly created entitlements', async () => {
       const say = sinon.stub().resolves();
       const entitlementResults = [
         { product: 'ASO', entitlementId: 'ent-1', enrollmentId: 'enr-1' },
@@ -371,32 +416,51 @@ describe('Modal Utils', () => {
       await modalUtils.postEntitlementMessages(say, entitlementResults, siteId);
 
       expect(say.calledTwice).to.be.true;
+      expect(say.getCall(0).args[0]).to.include('Created');
       expect(say.getCall(0).args[0]).to.include('ASO');
       expect(say.getCall(0).args[0]).to.include('ent-1');
       expect(say.getCall(0).args[0]).to.include('enr-1');
-      expect(say.getCall(0).args[0]).to.include('site123');
       expect(say.getCall(0).args[0]).to.include(EntitlementModel.TIERS.FREE_TRIAL);
 
+      expect(say.getCall(1).args[0]).to.include('Created');
       expect(say.getCall(1).args[0]).to.include('LLMO');
       expect(say.getCall(1).args[0]).to.include('ent-2');
       expect(say.getCall(1).args[0]).to.include('enr-2');
-      expect(say.getCall(1).args[0]).to.include('site123');
     });
 
-    it('posts message for single entitlement result', async () => {
+    it('posts already-existed message when entitlement and enrollment existed', async () => {
       const say = sinon.stub().resolves();
       const entitlementResults = [
-        { product: 'ASO', entitlementId: 'ent-123', enrollmentId: 'enr-456' },
+        {
+          product: 'ASO', entitlementId: 'ent-123', enrollmentId: 'enr-456', existingTier: 'PAID', alreadyExisted: true,
+        },
       ];
       const siteId = 'site789';
 
       await modalUtils.postEntitlementMessages(say, entitlementResults, siteId);
 
       expect(say.calledOnce).to.be.true;
-      expect(say.getCall(0).args[0]).to.include('ASO');
+      expect(say.getCall(0).args[0]).to.include('already exist');
+      expect(say.getCall(0).args[0]).to.include('PAID');
       expect(say.getCall(0).args[0]).to.include('ent-123');
-      expect(say.getCall(0).args[0]).to.include('enr-456');
-      expect(say.getCall(0).args[0]).to.include('site789');
+    });
+
+    it('posts enrollment-created message when entitlement existed but enrollment was new', async () => {
+      const say = sinon.stub().resolves();
+      const entitlementResults = [
+        {
+          product: 'ASO', entitlementId: 'ent-123', enrollmentId: 'enr-new', existingTier: 'PLG', enrollmentCreated: true,
+        },
+      ];
+      const siteId = 'site789';
+
+      await modalUtils.postEntitlementMessages(say, entitlementResults, siteId);
+
+      expect(say.calledOnce).to.be.true;
+      expect(say.getCall(0).args[0]).to.include('already existed');
+      expect(say.getCall(0).args[0]).to.include('created enrollment');
+      expect(say.getCall(0).args[0]).to.include('PLG');
+      expect(say.getCall(0).args[0]).to.include('enr-new');
     });
 
     it('does not post messages for empty results', async () => {
diff --git a/test/support/slack/actions/entitlement-modals.test.js b/test/support/slack/actions/entitlement-modals.test.js
index b44d1ffcf..676d10d8c 100644
--- a/test/support/slack/actions/entitlement-modals.test.js
+++ b/test/support/slack/actions/entitlement-modals.test.js
@@ -155,6 +155,7 @@ describe('EntitlementModals', () => {
             revokeSiteEnrollment: sinon.stub().resolves(),
           }),
           createForOrg: sinon.stub().returns({
+            checkValidEntitlement: sinon.stub().resolves({}),
             createEntitlement: sinon.stub().resolves({
               entitlement: { getId: () => TEST_IDS.ent },
             }),
@@ -397,15 +398,55 @@ describe('EntitlementModals', () => {
       );
     });
 
+    it('preserves existing entitlement and skips creation', async () => {
+      const existingEntitlement = {
+        getId: () => 'ent-existing',
+        getTier: () => 'PLG',
+      };
+      const mockTierClientInstance = {
+        checkValidEntitlement: sinon.stub().resolves({ entitlement: existingEntitlement }),
+      };
+
+      const module = await esmock('../../../../src/support/slack/actions/entitlement-modals.js', {
+        '@adobe/spacecat-shared-tier-client': {
+          default: {
+            createForOrg: sinon.stub().returns(mockTierClientInstance),
+          },
+        },
+        '../../../../src/support/slack/actions/entitlement-modal-utils.js': {
+          extractSelectedProducts: await import('../../../../src/support/slack/actions/entitlement-modal-utils.js')
+            .then((m) => m.extractSelectedProducts),
+          createSayFunction: await import('../../../../src/support/slack/actions/entitlement-modal-utils.js')
+            .then((m) => m.createSayFunction),
+          updateMessageToProcessing: mockUpdateMessageToProcessing,
+        },
+      });
+
+      await testModalSubmission(
+        module.ensureEntitlementImsOrgModal,
+        createOrgMetadata(),
+        createProductState(),
+        (ack, client) => {
+          expect(ack).to.have.been.calledOnce;
+          expect(client.chat.postMessage).to.have.been.calledWith(sinon.match({
+            text: sinon.match('already exists'),
+          }));
+          expect(client.chat.postMessage).to.have.been.calledWith(sinon.match({
+            text: sinon.match('PLG'),
+          }));
+        },
+      );
+    });
+
     it('handles errors during individual product entitlement', async () => {
-      const mockTierClient = {
-        createEntitlement: sinon.stub().rejects(new Error('Tier error')),
+      const mockTierClientInstance = {
+        checkValidEntitlement: sinon.stub().rejects(new Error('Tier error')),
       };
 
       const module = await esmock('../../../../src/support/slack/actions/entitlement-modals.js', {
         '@adobe/spacecat-shared-tier-client': {
           default: {
-            createForOrg: sinon.stub().returns(mockTierClient),
+            createForOrg: sinon.stub().returns(mockTierClientInstance),
           },
         },
         '../../../../src/support/slack/actions/entitlement-modal-utils.js': {