diff --git a/libs/vault/src/services/default-vault-items-transfer.service.spec.ts b/libs/vault/src/services/default-vault-items-transfer.service.spec.ts
index f5da99cae61..b7d24681e64 100644
--- a/libs/vault/src/services/default-vault-items-transfer.service.spec.ts
+++ b/libs/vault/src/services/default-vault-items-transfer.service.spec.ts
@@ -938,4 +938,142 @@ describe("DefaultVaultItemsTransferService", () => {
       expect(transferInProgressValues).toEqual([false, true, false]);
     });
   });
+
+  describe("enforcementInFlight", () => {
+    const policy = {
+      organizationId: organizationId,
+      revisionDate: new Date("2024-01-01"),
+    } as Policy;
+    const organization = {
+      id: organizationId,
+      name: "Test Org",
+    } as Organization;
+    const personalCiphers = [{ id: "cipher-1" } as CipherView];
+    const defaultCollection = {
+      id: collectionId,
+      organizationId: organizationId,
+      isDefaultCollection: true,
+    } as CollectionView;
+
+    beforeEach(() => {
+      mockConfigService.getFeatureFlag.mockResolvedValue(true);
+      mockPolicyService.policiesByType$.mockReturnValue(of([policy]));
+      mockOrganizationService.organizations$.mockReturnValue(of([organization]));
+      mockCipherService.cipherViews$.mockReturnValue(of(personalCiphers));
+      mockCollectionService.defaultUserCollection$.mockReturnValue(of(defaultCollection));
+      mockSyncService.fullSync.mockResolvedValue(true);
+      mockOrganizationUserApiService.revokeSelf.mockResolvedValue(undefined);
+    });
+
+    it("prevents re-entry when enforcement is already in flight", async () => {
+      // Create a dialog that resolves after a delay
+      const delayedSubject = new Subject<any>();
+      const delayedDialog = {
+        closed: delayedSubject.asObservable(),
+        close: jest.fn(),
+      } as unknown as DialogRef<any>;
+
+      mockDialogService.open.mockReturnValue(delayedDialog);
+
+      // Start first call (won't complete immediately)
+      const firstCall = service.enforceOrganizationDataOwnership(userId);
+
+      // Flush microtasks to allow first call to set enforcementInFlight
+      await Promise.resolve();
+
+      // Second call should return immediately without opening dialog
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Verify re-entry was prevented - only the first call should proceed
+      expect(mockDialogService.open).toHaveBeenCalledTimes(1);
+      expect(mockPolicyService.policiesByType$).toHaveBeenCalledTimes(1);
+
+      // Clean up - resolve the first call's dialog
+      delayedSubject.next(TransferItemsDialogResult.Declined);
+      delayedSubject.complete();
+
+      // Mock the leave dialog
+      mockDialogService.open.mockReturnValueOnce(
+        createMockDialogRef(LeaveConfirmationDialogResult.Confirmed),
+      );
+
+      await firstCall;
+    });
+
+    it("allows subsequent calls after user declines and leaves", async () => {
+      // First call: user declines and confirms leaving
+      mockDialogService.open
+        .mockReturnValueOnce(createMockDialogRef(TransferItemsDialogResult.Declined))
+        .mockReturnValueOnce(createMockDialogRef(LeaveConfirmationDialogResult.Confirmed));
+
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Reset mocks for second call
+      mockDialogService.open.mockClear();
+
+      // Second call: user accepts transfer
+      mockDialogService.open.mockReturnValueOnce(
+        createMockDialogRef(TransferItemsDialogResult.Accepted),
+      );
+      mockCipherService.shareManyWithServer.mockResolvedValue(undefined);
+
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Second call should proceed (dialog opened again)
+      expect(mockDialogService.open).toHaveBeenCalledTimes(1);
+    });
+
+    it("allows subsequent calls after successful transfer", async () => {
+      // First call: user accepts transfer
+      mockDialogService.open.mockReturnValueOnce(
+        createMockDialogRef(TransferItemsDialogResult.Accepted),
+      );
+      mockCipherService.shareManyWithServer.mockResolvedValue(undefined);
+
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Reset mocks for second call
+      mockDialogService.open.mockClear();
+      mockCipherService.shareManyWithServer.mockClear();
+
+      // Second call should be allowed (though no migration needed after first transfer)
+      // Set up scenario where migration is needed again
+      mockCipherService.cipherViews$.mockReturnValue(of([{ id: "cipher-2" } as CipherView]));
+
+      mockDialogService.open.mockReturnValueOnce(
+        createMockDialogRef(TransferItemsDialogResult.Accepted),
+      );
+      mockCipherService.shareManyWithServer.mockResolvedValue(undefined);
+
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Second call should proceed (dialog opened again)
+      expect(mockDialogService.open).toHaveBeenCalledTimes(1);
+    });
+
+    it("allows subsequent calls after transfer fails with error", async () => {
+      // First call: transfer fails
+      mockDialogService.open.mockReturnValueOnce(
+        createMockDialogRef(TransferItemsDialogResult.Accepted),
+      );
+      mockCipherService.shareManyWithServer.mockRejectedValue(new Error("Transfer failed"));
+
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Reset mocks for second call
+      mockDialogService.open.mockClear();
+      mockCipherService.shareManyWithServer.mockClear();
+
+      // Second call: user accepts transfer successfully
+      mockDialogService.open.mockReturnValueOnce(
+        createMockDialogRef(TransferItemsDialogResult.Accepted),
+      );
+      mockCipherService.shareManyWithServer.mockResolvedValue(undefined);
+
+      await service.enforceOrganizationDataOwnership(userId);
+
+      // Second call should proceed (dialog opened again)
+      expect(mockDialogService.open).toHaveBeenCalledTimes(1);
+    });
+  });
 });
diff --git a/libs/vault/src/services/default-vault-items-transfer.service.ts b/libs/vault/src/services/default-vault-items-transfer.service.ts
index 3e65d3157f5..8b1c24c8ca2 100644
--- a/libs/vault/src/services/default-vault-items-transfer.service.ts
+++ b/libs/vault/src/services/default-vault-items-transfer.service.ts
@@ -62,6 +62,12 @@ export class DefaultVaultItemsTransferService implements VaultItemsTransferServi
 
   transferInProgress$ = this._transferInProgressSubject.asObservable();
 
+  /**
+   * Only a single enforcement should be allowed to run at a time to prevent multiple dialogs
+   * or multiple simultaneous transfers.
+   */
+  private enforcementInFlight: boolean = false;
+
   private enforcingOrganization$(userId: UserId): Observable<Organization | undefined> {
     return this.policyService.policiesByType$(PolicyType.OrganizationDataOwnership, userId).pipe(
       map(
@@ -142,7 +148,7 @@ export class DefaultVaultItemsTransferService implements VaultItemsTransferServi
       FeatureFlag.MigrateMyVaultToMyItems,
     );
 
-    if (!featureEnabled) {
+    if (!featureEnabled || this.enforcementInFlight) {
       return;
     }
 
@@ -160,6 +166,8 @@ export class DefaultVaultItemsTransferService implements VaultItemsTransferServi
       return;
     }
 
+    this.enforcementInFlight = true;
+
     const userAcceptedTransfer = await this.promptUserForTransfer(
       migrationInfo.enforcingOrganization.name,
     );
@@ -179,6 +187,7 @@ export class DefaultVaultItemsTransferService implements VaultItemsTransferServi
       );
       // Sync to reflect organization removal
       await this.syncService.fullSync(true);
+      this.enforcementInFlight = false;
       return;
     }
 
@@ -208,6 +217,8 @@ export class DefaultVaultItemsTransferService implements VaultItemsTransferServi
         variant: "error",
         message: this.i18nService.t("errorOccurred"),
       });
+    } finally {
+      this.enforcementInFlight = false;
     }
   }