diff --git a/src/Core/Core.csproj b/src/Core/Core.csproj
index 36c56ad013..9d8b709abc 100644
--- a/src/Core/Core.csproj
+++ b/src/Core/Core.csproj
@@ -37,7 +37,7 @@
     <PackageReference Include="Braintree" Version="4.5.0" />
     <PackageReference Include="Portable.BouncyCastle" Version="1.8.2" />
     <PackageReference Include="Sendgrid" Version="9.9.0" />
-    <PackageReference Include="Stripe.net" Version="17.8.0" />
+    <PackageReference Include="Stripe.net" Version="19.6.0" />
     <PackageReference Include="U2F.Core" Version="1.0.4" />
     <PackageReference Include="Otp.NET" Version="1.2.0" />
     <PackageReference Include="YubicoDotNetClient" Version="1.2.0" />
diff --git a/src/Core/Services/Implementations/OrganizationService.cs b/src/Core/Services/Implementations/OrganizationService.cs
index 67d9b2eb69..de1503d778 100644
--- a/src/Core/Services/Implementations/OrganizationService.cs
+++ b/src/Core/Services/Implementations/OrganizationService.cs
@@ -185,6 +185,7 @@ namespace Bit.Core.Services
                 // They must have been on a free plan. Create new sub.
                 var subCreateOptions = new StripeSubscriptionCreateOptions
                 {
+                    CustomerId = organization.GatewayCustomerId,
                     TrialPeriodDays = newPlan.TrialPeriodDays,
                     Items = new List<StripeSubscriptionItemOption>(),
                     Metadata = new Dictionary<string, string> {
@@ -210,7 +211,7 @@ namespace Bit.Core.Services
                     });
                 }
 
-                await subscriptionService.CreateAsync(organization.GatewayCustomerId, subCreateOptions);
+                await subscriptionService.CreateAsync(subCreateOptions);
             }
             else
             {
@@ -468,6 +469,7 @@ namespace Bit.Core.Services
 
                 var subCreateOptions = new StripeSubscriptionCreateOptions
                 {
+                    CustomerId = customer.Id,
                     TrialPeriodDays = plan.TrialPeriodDays,
                     Items = new List<StripeSubscriptionItemOption>(),
                     Metadata = new Dictionary<string, string> {
@@ -504,7 +506,7 @@ namespace Bit.Core.Services
 
                 try
                 {
-                    subscription = await subscriptionService.CreateAsync(customer.Id, subCreateOptions);
+                    subscription = await subscriptionService.CreateAsync(subCreateOptions);
                 }
                 catch(StripeException)
                 {
diff --git a/src/Core/Services/Implementations/StripePaymentService.cs b/src/Core/Services/Implementations/StripePaymentService.cs
index 8f74177f50..d95153c311 100644
--- a/src/Core/Services/Implementations/StripePaymentService.cs
+++ b/src/Core/Services/Implementations/StripePaymentService.cs
@@ -26,6 +26,7 @@ namespace Bit.Core.Services
 
             var subCreateOptions = new StripeSubscriptionCreateOptions
             {
+                CustomerId = customer.Id,
                 Items = new List<StripeSubscriptionItemOption>(),
                 Metadata = new Dictionary<string, string>
                 {
@@ -52,7 +53,7 @@ namespace Bit.Core.Services
             try
             {
                 var subscriptionService = new StripeSubscriptionService();
-                subscription = await subscriptionService.CreateAsync(customer.Id, subCreateOptions);
+                subscription = await subscriptionService.CreateAsync(subCreateOptions);
             }
             catch(StripeException)
             {
@@ -114,7 +115,8 @@ namespace Bit.Core.Services
             if(!string.IsNullOrWhiteSpace(subscriber.GatewaySubscriptionId))
             {
                 var subscriptionService = new StripeSubscriptionService();
-                await subscriptionService.CancelAsync(subscriber.GatewaySubscriptionId, false);
+                await subscriptionService.CancelAsync(subscriber.GatewaySubscriptionId,
+                    new StripeSubscriptionCancelOptions());
             }
 
             if(string.IsNullOrWhiteSpace(subscriber.GatewayCustomerId))
@@ -158,7 +160,7 @@ namespace Bit.Core.Services
                 try
                 {
                     // Owes more than prorateThreshold on next invoice.
-                    // Invoice them and pay now instead of waiting until next month.
+                    // Invoice them and pay now instead of waiting until next billing cycle.
                     var invoice = await invoiceService.CreateAsync(subscriber.GatewayCustomerId,
                         new StripeInvoiceCreateOptions
                         {
@@ -167,7 +169,7 @@ namespace Bit.Core.Services
 
                     if(invoice.AmountDue > 0)
                     {
-                        await invoiceService.PayAsync(invoice.Id);
+                        await invoiceService.PayAsync(invoice.Id, new StripeInvoicePayOptions());
                     }
                 }
                 catch(StripeException) { }
@@ -201,7 +203,10 @@ namespace Bit.Core.Services
 
             try
             {
-                var canceledSub = await subscriptionService.CancelAsync(sub.Id, endOfPeriod);
+                var canceledSub = endOfPeriod ?
+                    await subscriptionService.UpdateAsync(sub.Id,
+                        new StripeSubscriptionUpdateOptions { CancelAtPeriodEnd = true }) :
+                    await subscriptionService.CancelAsync(sub.Id, new StripeSubscriptionCancelOptions());
                 if(!canceledSub.CanceledAt.HasValue)
                 {
                     throw new GatewayException("Unable to cancel subscription.");