diff --git a/src/Api/Controllers/AccountsController.cs b/src/Api/Controllers/AccountsController.cs
index 740019795..703f7a8df 100644
--- a/src/Api/Controllers/AccountsController.cs
+++ b/src/Api/Controllers/AccountsController.cs
@@ -547,7 +547,7 @@ namespace Bit.Api.Controllers
                 throw new UnauthorizedAccessException();
             }
 
-            await _userService.CancelPremiumAsync(user, true);
+            await _userService.CancelPremiumAsync(user);
         }
 
         [HttpPost("reinstate-premium")]
diff --git a/src/Api/Controllers/OrganizationsController.cs b/src/Api/Controllers/OrganizationsController.cs
index 7f657db49..340b07908 100644
--- a/src/Api/Controllers/OrganizationsController.cs
+++ b/src/Api/Controllers/OrganizationsController.cs
@@ -284,7 +284,7 @@ namespace Bit.Api.Controllers
                 throw new NotFoundException();
             }
 
-            await _organizationService.CancelSubscriptionAsync(orgIdGuid, true);
+            await _organizationService.CancelSubscriptionAsync(orgIdGuid);
         }
 
         [HttpPost("{id}/reinstate")]
diff --git a/src/Core/Services/IOrganizationService.cs b/src/Core/Services/IOrganizationService.cs
index 181da0eb5..257cb5d1c 100644
--- a/src/Core/Services/IOrganizationService.cs
+++ b/src/Core/Services/IOrganizationService.cs
@@ -11,7 +11,7 @@ namespace Bit.Core.Services
     public interface IOrganizationService
     {
         Task ReplacePaymentMethodAsync(Guid organizationId, string paymentToken);
-        Task CancelSubscriptionAsync(Guid organizationId, bool endOfPeriod = false);
+        Task CancelSubscriptionAsync(Guid organizationId, bool? endOfPeriod = null);
         Task ReinstateSubscriptionAsync(Guid organizationId);
         Task UpgradePlanAsync(Guid organizationId, PlanType plan, int additionalSeats);
         Task AdjustStorageAsync(Guid organizationId, short storageAdjustmentGb);
diff --git a/src/Core/Services/IUserService.cs b/src/Core/Services/IUserService.cs
index cb763065b..0ee83ce77 100644
--- a/src/Core/Services/IUserService.cs
+++ b/src/Core/Services/IUserService.cs
@@ -47,7 +47,7 @@ namespace Bit.Core.Services
         Task UpdateLicenseAsync(User user, UserLicense license);
         Task AdjustStorageAsync(User user, short storageAdjustmentGb);
         Task ReplacePaymentMethodAsync(User user, string paymentToken);
-        Task CancelPremiumAsync(User user, bool endOfPeriod = false);
+        Task CancelPremiumAsync(User user, bool? endOfPeriod = null);
         Task ReinstatePremiumAsync(User user);
         Task DisablePremiumAsync(Guid userId, DateTime? expirationDate);
         Task DisablePremiumAsync(User user, DateTime? expirationDate);
diff --git a/src/Core/Services/Implementations/OrganizationService.cs b/src/Core/Services/Implementations/OrganizationService.cs
index 8776b49db..da6a5c8f6 100644
--- a/src/Core/Services/Implementations/OrganizationService.cs
+++ b/src/Core/Services/Implementations/OrganizationService.cs
@@ -85,7 +85,7 @@ namespace Bit.Core.Services
             }
         }
 
-        public async Task CancelSubscriptionAsync(Guid organizationId, bool endOfPeriod = false)
+        public async Task CancelSubscriptionAsync(Guid organizationId, bool? endOfPeriod = null)
         {
             var organization = await GetOrgById(organizationId);
             if(organization == null)
@@ -93,7 +93,14 @@ namespace Bit.Core.Services
                 throw new NotFoundException();
             }
 
-            await _stripePaymentService.CancelSubscriptionAsync(organization, endOfPeriod);
+            var eop = endOfPeriod.GetValueOrDefault(true);
+            if(!endOfPeriod.HasValue && organization.ExpirationDate.HasValue &&
+                organization.ExpirationDate.Value < DateTime.UtcNow)
+            {
+                eop = false;
+            }
+
+            await _stripePaymentService.CancelSubscriptionAsync(organization, eop);
         }
 
         public async Task ReinstateSubscriptionAsync(Guid organizationId)
diff --git a/src/Core/Services/Implementations/UserService.cs b/src/Core/Services/Implementations/UserService.cs
index fb6c46921..c7386cf92 100644
--- a/src/Core/Services/Implementations/UserService.cs
+++ b/src/Core/Services/Implementations/UserService.cs
@@ -820,10 +820,16 @@ namespace Bit.Core.Services
             }
         }
 
-        public async Task CancelPremiumAsync(User user, bool endOfPeriod = false)
+        public async Task CancelPremiumAsync(User user, bool? endOfPeriod = null)
         {
             var paymentService = user.GetPaymentService(_globalSettings);
-            await paymentService.CancelSubscriptionAsync(user, endOfPeriod);
+            var eop = endOfPeriod.GetValueOrDefault(true);
+            if(!endOfPeriod.HasValue && user.PremiumExpirationDate.HasValue &&
+                user.PremiumExpirationDate.Value < DateTime.UtcNow)
+            {
+                eop = false;
+            }
+            await paymentService.CancelSubscriptionAsync(user, eop);
         }
 
         public async Task ReinstatePremiumAsync(User user)