diff --git a/src/Admin/AdminConsole/Controllers/OrganizationsController.cs b/src/Admin/AdminConsole/Controllers/OrganizationsController.cs
index 6d38a77d8b..ecdd372df4 100644
--- a/src/Admin/AdminConsole/Controllers/OrganizationsController.cs
+++ b/src/Admin/AdminConsole/Controllers/OrganizationsController.cs
@@ -242,10 +242,32 @@ public class OrganizationsController : Controller
             Seats = organization.Seats
         };
 
+        if (model.PlanType.HasValue)
+        {
+            var freePlan = await _pricingClient.GetPlanOrThrow(model.PlanType.Value);
+            var isDowngradingToFree = organization.PlanType != PlanType.Free && model.PlanType.Value == PlanType.Free;
+            if (isDowngradingToFree)
+            {
+                if (model.Seats.HasValue && model.Seats.Value > freePlan.PasswordManager.MaxSeats)
+                {
+                    TempData["Error"] = $"Organizations with more than {freePlan.PasswordManager.MaxSeats} seats cannot be downgraded to the Free plan";
+                    return RedirectToAction("Edit", new { id });
+                }
+
+                if (model.MaxCollections > freePlan.PasswordManager.MaxCollections)
+                {
+                    TempData["Error"] = $"Organizations with more than {freePlan.PasswordManager.MaxCollections} collections cannot be downgraded to the Free plan. Your organization currently has {organization.MaxCollections} collections.";
+                    return RedirectToAction("Edit", new { id });
+                }
+
+                model.MaxStorageGb = null;
+                model.ExpirationDate = null;
+                model.Enabled = true;
+            }
+        }
+
         UpdateOrganization(organization, model);
-
         var plan = await _pricingClient.GetPlanOrThrow(organization.PlanType);
-
         if (organization.UseSecretsManager && !plan.SupportsSecretsManager)
         {
             TempData["Error"] = "Plan does not support Secrets Manager";
diff --git a/src/Api/Billing/Controllers/OrganizationBillingController.cs b/src/Api/Billing/Controllers/OrganizationBillingController.cs
index 071aae5060..f1ab1be6bd 100644
--- a/src/Api/Billing/Controllers/OrganizationBillingController.cs
+++ b/src/Api/Billing/Controllers/OrganizationBillingController.cs
@@ -4,6 +4,7 @@ using Bit.Api.AdminConsole.Models.Request.Organizations;
 using Bit.Api.Billing.Models.Requests;
 using Bit.Api.Billing.Models.Responses;
 using Bit.Api.Billing.Queries.Organizations;
+using Bit.Core.Billing.Enums;
 using Bit.Core.Billing.Models;
 using Bit.Core.Billing.Models.Sales;
 using Bit.Core.Billing.Pricing;
@@ -280,17 +281,36 @@ public class OrganizationBillingController(
         }
 
         var organization = await organizationRepository.GetByIdAsync(organizationId);
-
         if (organization == null)
         {
             return Error.NotFound();
         }
+        var existingPlan = organization.PlanType;
         var organizationSignup = model.ToOrganizationSignup(user);
         var sale = OrganizationSale.From(organization, organizationSignup);
         var plan = await pricingClient.GetPlanOrThrow(model.PlanType);
         sale.Organization.PlanType = plan.Type;
         sale.Organization.Plan = plan.Name;
         sale.SubscriptionSetup.SkipTrial = true;
+        if (existingPlan == PlanType.Free && organization.GatewaySubscriptionId is not null)
+        {
+            sale.Organization.UseTotp = plan.HasTotp;
+            sale.Organization.UseGroups = plan.HasGroups;
+            sale.Organization.UseDirectory = plan.HasDirectory;
+            sale.Organization.SelfHost = plan.HasSelfHost;
+            sale.Organization.UsersGetPremium = plan.UsersGetPremium;
+            sale.Organization.UseEvents = plan.HasEvents;
+            sale.Organization.Use2fa = plan.Has2fa;
+            sale.Organization.UseApi = plan.HasApi;
+            sale.Organization.UsePolicies = plan.HasPolicies;
+            sale.Organization.UseSso = plan.HasSso;
+            sale.Organization.UseResetPassword = plan.HasResetPassword;
+            sale.Organization.UseKeyConnector = plan.HasKeyConnector;
+            sale.Organization.UseScim = plan.HasScim;
+            sale.Organization.UseCustomPermissions = plan.HasCustomPermissions;
+            sale.Organization.UseOrganizationDomains = plan.HasOrganizationDomains;
+            sale.Organization.MaxCollections = plan.PasswordManager.MaxCollections;
+        }
 
         if (organizationSignup.PaymentMethodType == null || string.IsNullOrEmpty(organizationSignup.PaymentToken))
         {