diff --git a/src/Core/Services/Implementations/LicensingService.cs b/src/Core/Services/Implementations/LicensingService.cs
index d32689aca..2ff14cbe4 100644
--- a/src/Core/Services/Implementations/LicensingService.cs
+++ b/src/Core/Services/Implementations/LicensingService.cs
@@ -62,25 +62,35 @@ namespace Bit.Core.Services
                 return;
             }
 
-            var orgs = await _organizationRepository.GetManyByEnabledAsync();
-            _logger.LogInformation("Validating licenses for {0} organizations.", orgs.Count);
+            var enabledOrgs = await _organizationRepository.GetManyByEnabledAsync();
+            _logger.LogInformation("Validating licenses for {0} organizations.", enabledOrgs.Count);
 
-            foreach(var org in orgs)
+            foreach(var org in enabledOrgs)
             {
                 var license = ReadOrganiztionLicense(org);
-                if(license == null || !license.VerifyData(org, _globalSettings) || !license.VerifySignature(_certificate))
+                if(license == null)
                 {
-                    _logger.LogInformation("Organization {0}({1}) has an invalid license and is being disabled.",
-                        org.Id, org.Name);
+                    await DisableOrganizationAsync(org, null);
+                    continue;
+                }
 
-                    org.Enabled = false;
-                    org.ExpirationDate = license.Expires;
-                    org.RevisionDate = DateTime.UtcNow;
-                    await _organizationRepository.ReplaceAsync(org);
+                var totalLicensedOrgs = enabledOrgs.Count(o => o.LicenseKey.Equals(license.LicenseKey));
+                if(totalLicensedOrgs > 1 || !license.VerifyData(org, _globalSettings) || !license.VerifySignature(_certificate))
+                {
+                    await DisableOrganizationAsync(org, license);
                 }
             }
         }
 
+        private async Task DisableOrganizationAsync(Organization org, ILicense license)
+        {
+            _logger.LogInformation("Organization {0}({1}) has an invalid license and is being disabled.", org.Id, org.Name);
+            org.Enabled = false;
+            org.ExpirationDate = license?.Expires ?? DateTime.UtcNow;
+            org.RevisionDate = DateTime.UtcNow;
+            await _organizationRepository.ReplaceAsync(org);
+        }
+
         public async Task ValidateUsersAsync()
         {
             if(!_globalSettings.SelfHosted)
@@ -178,7 +188,7 @@ namespace Bit.Core.Services
                     user.Id, user.Email);
 
                 user.Premium = false;
-                user.PremiumExpirationDate = license.Expires;
+                user.PremiumExpirationDate = license?.Expires ?? DateTime.UtcNow;
                 user.RevisionDate = DateTime.UtcNow;
                 await _userRepository.ReplaceAsync(user);
             }
diff --git a/src/Core/Services/Implementations/OrganizationService.cs b/src/Core/Services/Implementations/OrganizationService.cs
index ac313a231..a4b30da53 100644
--- a/src/Core/Services/Implementations/OrganizationService.cs
+++ b/src/Core/Services/Implementations/OrganizationService.cs
@@ -555,12 +555,18 @@ namespace Bit.Core.Services
                     "hosting of organizations and that the installation id matches your current installation.");
             }
 
-            if(license.PlanType != PlanType.Custom && 
+            if(license.PlanType != PlanType.Custom &&
                 StaticStore.Plans.FirstOrDefault(p => p.Type == license.PlanType && !p.Disabled) == null)
             {
                 throw new BadRequestException("Plan not found.");
             }
 
+            var enabledOrgs = await _organizationRepository.GetManyByEnabledAsync();
+            if(enabledOrgs.Any(o => o.LicenseKey.Equals(license.LicenseKey)))
+            {
+                throw new BadRequestException("License is already in use by another organization.");
+            }
+
             var organization = new Organization
             {
                 Name = license.Name,
@@ -683,6 +689,12 @@ namespace Bit.Core.Services
                     "hosting of organizations and that the installation id matches your current installation.");
             }
 
+            var enabledOrgs = await _organizationRepository.GetManyByEnabledAsync();
+            if(enabledOrgs.Any(o => o.LicenseKey.Equals(license.LicenseKey) && o.Id != organizationId))
+            {
+                throw new BadRequestException("License is already in use by another organization.");
+            }
+
             if(license.Seats.HasValue && (!organization.Seats.HasValue || organization.Seats.Value > license.Seats.Value))
             {
                 var userCount = await _organizationUserRepository.GetCountByOrganizationIdAsync(organization.Id);