diff --git a/src/Billing/Startup.cs b/src/Billing/Startup.cs
index ec4cefe40b..5007536ff6 100644
--- a/src/Billing/Startup.cs
+++ b/src/Billing/Startup.cs
@@ -50,6 +50,9 @@ namespace Bit.Billing
             // Repositories
             services.AddSqlServerRepositories();
 
+            // Context
+            services.AddScoped<CurrentContext>();
+
             // Services
             services.AddBaseServices();
             services.AddDefaultServices();
diff --git a/src/Core/Models/StaticStore/Plan.cs b/src/Core/Models/StaticStore/Plan.cs
index 08e5bc7bce..1b81e09dc5 100644
--- a/src/Core/Models/StaticStore/Plan.cs
+++ b/src/Core/Models/StaticStore/Plan.cs
@@ -16,5 +16,6 @@ namespace Bit.Core.Models.StaticStore
         public short? MaxSubvaults { get; set; }
         public int UpgradeSortOrder { get; set; }
         public bool Disabled { get; set; }
+        public int? TrialPeriodDays { get; set; }
     }
 }
diff --git a/src/Core/Services/Implementations/OrganizationService.cs b/src/Core/Services/Implementations/OrganizationService.cs
index cb6057ac6b..378beaad9c 100644
--- a/src/Core/Services/Implementations/OrganizationService.cs
+++ b/src/Core/Services/Implementations/OrganizationService.cs
@@ -287,6 +287,7 @@ namespace Bit.Core.Services
                 // They must have been on a free plan. Create new sub.
                 var subCreateOptions = new StripeSubscriptionCreateOptions
                 {
+                    TrialPeriodDays = newPlan.TrialPeriodDays,
                     Items = new List<StripeSubscriptionItemOption>
                     {
                         new StripeSubscriptionItemOption
@@ -504,6 +505,7 @@ namespace Bit.Core.Services
 
                 var subCreateOptions = new StripeSubscriptionCreateOptions
                 {
+                    TrialPeriodDays = plan.TrialPeriodDays,
                     Items = new List<StripeSubscriptionItemOption>
                     {
                         new StripeSubscriptionItemOption
diff --git a/src/Core/Utilities/StaticStore.cs b/src/Core/Utilities/StaticStore.cs
index 588e69c5f9..82b0f6b24d 100644
--- a/src/Core/Utilities/StaticStore.cs
+++ b/src/Core/Utilities/StaticStore.cs
@@ -111,7 +111,8 @@ namespace Bit.Core.Utilities
                     Name = "Personal",
                     StripePlanId = "personal-org-annually",
                     StripeSeatPlanId = "personal-org-seat-annually",
-                    UpgradeSortOrder = 1
+                    UpgradeSortOrder = 1,
+                    TrialPeriodDays = 7
                 },
                 new Plan
                 {
@@ -123,7 +124,8 @@ namespace Bit.Core.Utilities
                     Name = "Teams (Monthly)",
                     StripePlanId = "teams-org-monthly",
                     StripeSeatPlanId = "teams-org-seat-monthly",
-                    UpgradeSortOrder = 2
+                    UpgradeSortOrder = 2,
+                    TrialPeriodDays = 7
                 },
                 new Plan
                 {
@@ -135,7 +137,8 @@ namespace Bit.Core.Utilities
                     Name = "Teams (Annually)",
                     StripePlanId = "teams-org-annually",
                     StripeSeatPlanId = "teams-org-seat-annually",
-                    UpgradeSortOrder = 2
+                    UpgradeSortOrder = 2,
+                    TrialPeriodDays = 7
                 }
             };