diff --git a/app/controllers/billing_controller.rb b/app/controllers/billing_controller.rb
index bf2879bb..ba5e2cc1 100644
--- a/app/controllers/billing_controller.rb
+++ b/app/controllers/billing_controller.rb
@@ -123,17 +123,18 @@ class BillingController < ApplicationController
         TenantMailer.subscription_confirmation(tenant: Current.tenant).deliver_later
       end
     elsif event['type'] == 'customer.subscription.updated'
+      # This event is triggered when:
+      # (1) A subscription is canceled OR a subscription is reactivated after being canceled
+      # (2) A subscription is updated (e.g. switching from monthly to yearly plan or vice versa)
+      # (3) A subscription is automatically renewed at the end of the billing period (e.g. every month for a monthly subscription)
+      # Since it is difficult to distinguish between these cases, we only update the status if the subscription is active or canceled
+      # and we do not send any emails notifications.
+
       Current.tenant = get_tenant_from_customer_id(event.data.object.customer)
 
       if Current.tenant.tenant_billing.status == 'active' || Current.tenant.tenant_billing.status == 'canceled'
         has_canceled = event.data.object.cancel_at_period_end
         Current.tenant.tenant_billing.update!(status: has_canceled ? 'canceled' : 'active')
-
-        if has_canceled
-          TenantMailer.cancellation_confirmation(tenant: Current.tenant).deliver_later
-        else
-          TenantMailer.renewal_confirmation(tenant: Current.tenant).deliver_later
-        end
       end
     end
 
diff --git a/lib/tasks/notify_tenants_trial_period.rake b/lib/tasks/notify_tenants_trial_period.rake
index 79725e4c..ef6dd072 100644
--- a/lib/tasks/notify_tenants_trial_period.rake
+++ b/lib/tasks/notify_tenants_trial_period.rake
@@ -8,7 +8,20 @@ def get_tenants_to_notify(period)
     trial_ends_at: date_to_check.beginning_of_day..date_to_check.end_of_day,
     status: 'trial'
   )
-  Tenant.where(id: tbs.map(&:tenant_id))
+  tenants_to_notify = Tenant.where(id: tbs.map(&:tenant_id))
+
+  # If notifying for "mid" trial period, check whether tenant has not been granted an extension of the trial period
+  # An extended trial period usually means that the tenant contacted me personally, so there is no need to send
+  # a "mid" trial period notification (which could also be sent multiple times in the case of an extension)
+  # So we filter out tenants whose trial_ends_at is not 7 days after the tenant created at date
+  if period == "mid"
+    tenants_to_notify = tenants_to_notify.select do |tenant|
+      tenant_billing = TenantBilling.unscoped.find_by(tenant_id: tenant.id)
+      tenant_billing.trial_ends_at.to_date == tenant.created_at.to_date + 7.days
+    end
+  end
+
+  tenants_to_notify
 end
 
 task notify_tenants_trial_period: [:environment] do