diff --git a/billing/checkout/service.go b/billing/checkout/service.go
index ee77a9861..683fb7f9e 100644
--- a/billing/checkout/service.go
+++ b/billing/checkout/service.go
@@ -956,6 +956,14 @@ func (s *Service) Apply(ctx context.Context, ch Checkout) (*subscription.Subscri
 		if err != nil {
 			return nil, nil, fmt.Errorf("failed to create subscription: %w", err)
 		}
+
+		// if set to cancel after trial, schedule a phase to cancel the subscription
+		if ch.CancelAfterTrial && stripeSubscription.TrialEnd > 0 {
+			_, err := s.subscriptionService.Cancel(ctx, subs.ID, false)
+			if err != nil {
+				return nil, nil, fmt.Errorf("failed to schedule cancel of subscription after trial: %w", err)
+			}
+		}
 		return &subs, nil, nil
 	} else if ch.ProductID != "" {
 		chProduct, err := s.productService.GetByID(ctx, ch.ProductID)
diff --git a/billing/config.go b/billing/config.go
index 40e8d626e..f7844c48b 100644
--- a/billing/config.go
+++ b/billing/config.go
@@ -26,10 +26,11 @@ type RefreshInterval struct {
 }
 
 type AccountConfig struct {
-	AutoCreateWithOrg     bool   `yaml:"auto_create_with_org" mapstructure:"auto_create_with_org"`
-	DefaultPlan           string `yaml:"default_plan" mapstructure:"default_plan"`
-	DefaultOffline        bool   `yaml:"default_offline" mapstructure:"default_offline"`
-	OnboardCreditsWithOrg int64  `yaml:"onboard_credits_with_org" mapstructure:"onboard_credits_with_org"`
+	AutoCreateWithOrg           bool   `yaml:"auto_create_with_org" mapstructure:"auto_create_with_org"`
+	DefaultPlan                 string `yaml:"default_plan" mapstructure:"default_plan"`
+	DefaultOffline              bool   `yaml:"default_offline" mapstructure:"default_offline"`
+	OnboardCreditsWithOrg       int64  `yaml:"onboard_credits_with_org" mapstructure:"onboard_credits_with_org"`
+	DefaultPlanCancelAfterTrial bool   `yaml:"default_plan_cancel_after_trial" mapstructure:"default_plan_cancel_after_trial"`
 }
 
 type PlanChangeConfig struct {
diff --git a/core/event/service.go b/core/event/service.go
index 25762f3e2..065d7f1de 100644
--- a/core/event/service.go
+++ b/core/event/service.go
@@ -135,17 +135,20 @@ func (p *Service) EnsureDefaultPlan(ctx context.Context, orgID string) error {
 				return fmt.Errorf("failed to get default plan: %w", err)
 			}
 
+			var totalPrice int64
 			for _, prod := range defaultPlan.Products {
 				for _, price := range prod.Prices {
-					if price.Amount > 0 {
-						return fmt.Errorf("default plan is not free")
-					}
+					totalPrice += price.Amount
 				}
 			}
+			if totalPrice > 0 && defaultPlan.TrialDays == 0 {
+				return fmt.Errorf("default plan is not free to start")
+			}
+
 			_, _, err = p.checkoutService.Apply(ctx, checkout.Checkout{
-				CustomerID: customr.ID,
-				PlanID:     defaultPlan.ID,
-				SkipTrial:  true,
+				CustomerID:       customr.ID,
+				PlanID:           defaultPlan.ID,
+				CancelAfterTrial: p.billingConf.AccountConfig.DefaultPlanCancelAfterTrial,
 			})
 			if err != nil {
 				return fmt.Errorf("failed to apply default plan: %w", err)