diff --git a/src/Core/Services/Implementations/OrganizationSponsorshipService.cs b/src/Core/Services/Implementations/OrganizationSponsorshipService.cs
index faf1967979..8dbd07e38b 100644
--- a/src/Core/Services/Implementations/OrganizationSponsorshipService.cs
+++ b/src/Core/Services/Implementations/OrganizationSponsorshipService.cs
@@ -98,7 +98,7 @@ namespace Bit.Core.Services
 
             var existingOrgSponsorship = await _organizationSponsorshipRepository
                 .GetBySponsoringOrganizationUserIdAsync(sponsoringOrgUser.Id);
-            if (existingOrgSponsorship != null)
+            if (existingOrgSponsorship?.SponsoredOrganizationId != null)
             {
                 throw new BadRequestException("Can only sponsor one organization per Organization User.");
             }
@@ -113,9 +113,15 @@ namespace Bit.Core.Services
                 CloudSponsor = true,
             };
 
+            if (existingOrgSponsorship != null)
+            {
+                // Replace existing invalid offer with our new sponsorship offer
+                sponsorship.Id = existingOrgSponsorship.Id;
+            }
+
             try
             {
-                sponsorship = await _organizationSponsorshipRepository.CreateAsync(sponsorship);
+                await _organizationSponsorshipRepository.UpsertAsync(sponsorship);
 
                 await SendSponsorshipOfferAsync(sponsorship, sponsoringUserEmail);
             }
diff --git a/test/Core.Test/Services/OrganizationSponsorshipServiceTests.cs b/test/Core.Test/Services/OrganizationSponsorshipServiceTests.cs
index c17a4d21ba..ebd1c05a09 100644
--- a/test/Core.Test/Services/OrganizationSponsorshipServiceTests.cs
+++ b/test/Core.Test/Services/OrganizationSponsorshipServiceTests.cs
@@ -139,7 +139,7 @@ namespace Bit.Core.Test.Services
             };
 
             await sutProvider.GetDependency<IOrganizationSponsorshipRepository>().Received(1)
-                .CreateAsync(Arg.Is<OrganizationSponsorship>(s => SponsorshipValidator(s, expectedSponsorship)));
+                .UpsertAsync(Arg.Is<OrganizationSponsorship>(s => SponsorshipValidator(s, expectedSponsorship)));
 
             await sutProvider.GetDependency<IMailService>().Received(1).
                 SendFamiliesForEnterpriseOfferEmailAsync(sponsoredEmail, email,
@@ -156,7 +156,7 @@ namespace Bit.Core.Test.Services
 
             var expectedException = new Exception();
             OrganizationSponsorship createdSponsorship = null;
-            sutProvider.GetDependency<IOrganizationSponsorshipRepository>().CreateAsync(default).ThrowsForAnyArgs(callInfo =>
+            sutProvider.GetDependency<IOrganizationSponsorshipRepository>().UpsertAsync(default).ThrowsForAnyArgs(callInfo =>
             {
                 createdSponsorship = callInfo.ArgAt<OrganizationSponsorship>(0);
                 createdSponsorship.Id = Guid.NewGuid();