diff --git a/app/mailers/enterprise_mailer.rb b/app/mailers/enterprise_mailer.rb
index c64907cf6a..95a888e229 100644
--- a/app/mailers/enterprise_mailer.rb
+++ b/app/mailers/enterprise_mailer.rb
@@ -23,7 +23,8 @@ class EnterpriseMailer < ApplicationMailer
     I18n.with_locale valid_locale(@enterprise.owner) do
       subject = t('enterprise_mailer.invite_manager.subject', enterprise: @enterprise.name)
       mail(to: user.email,
-           subject:)
+           subject:,
+           reply_to: @enterprise.contact.email)
     end
   end
 
diff --git a/app/mailers/payment_mailer.rb b/app/mailers/payment_mailer.rb
index ae38604b98..97db37e053 100644
--- a/app/mailers/payment_mailer.rb
+++ b/app/mailers/payment_mailer.rb
@@ -5,10 +5,13 @@ class PaymentMailer < ApplicationMailer
 
   def authorize_payment(payment)
     @payment = payment
+    @order = @payment.order
     subject = I18n.t('spree.payment_mailer.authorize_payment.subject',
-                     distributor: @payment.order.distributor.name)
-    I18n.with_locale valid_locale(@payment.order.user) do
-      mail(to: payment.order.email, subject:)
+                     distributor: @order.distributor.name)
+    I18n.with_locale valid_locale(@order.user) do
+      mail(to: @order.email,
+           subject:,
+           reply_to: @order.distributor.contact.email)
     end
   end
 
diff --git a/app/mailers/spree/order_mailer.rb b/app/mailers/spree/order_mailer.rb
index 97ffd3f6b1..e4d886d3e9 100644
--- a/app/mailers/spree/order_mailer.rb
+++ b/app/mailers/spree/order_mailer.rb
@@ -13,7 +13,8 @@ module Spree
       @order = find_order(order_or_order_id)
       I18n.with_locale valid_locale(@order.user) do
         mail(to: @order.email,
-             subject: mail_subject(t('spree.order_mailer.cancel_email.subject'), resend))
+             subject: mail_subject(t('spree.order_mailer.cancel_email.subject'), resend),
+             reply_to: @order.distributor.contact.email)
       end
     end
 
diff --git a/app/mailers/spree/shipment_mailer.rb b/app/mailers/spree/shipment_mailer.rb
index 0be7b55cca..7b9216335b 100644
--- a/app/mailers/spree/shipment_mailer.rb
+++ b/app/mailers/spree/shipment_mailer.rb
@@ -5,8 +5,11 @@ module Spree
     def shipped_email(shipment, delivery:)
       @shipment = shipment.respond_to?(:id) ? shipment : Spree::Shipment.find(shipment)
       @delivery = delivery
+      @order = @shipment.order
       subject = base_subject
-      mail(to: @shipment.order.email, subject:)
+      mail(to: @order.email,
+           subject:,
+           reply_to: @order.distributor.contact.email)
     end
 
     private