diff --git a/app/presenters/mail_presenter.rb b/app/presenters/mail_presenter.rb
index 62cb0ed9a..cfd503976 100644
--- a/app/presenters/mail_presenter.rb
+++ b/app/presenters/mail_presenter.rb
@@ -176,7 +176,9 @@ class MailPresenter < SimpleDelegator
   def notification_email_from_chatwoot?
     # notification emails are send via mailer sender email address. so it should match
     configured_sender = Mail::Address.new(ENV.fetch('MAILER_SENDER_EMAIL', 'Chatwoot <accounts@chatwoot.com>')).address
-    original_sender.to_s.casecmp?(configured_sender)
+    actual_sender = parse_mail_address(@mail[:from]&.value)&.address
+
+    actual_sender.to_s.casecmp?(configured_sender)
   end
 
   private
diff --git a/spec/presenters/mail_presenter_spec.rb b/spec/presenters/mail_presenter_spec.rb
index f5ed27537..2643561c3 100644
--- a/spec/presenters/mail_presenter_spec.rb
+++ b/spec/presenters/mail_presenter_spec.rb
@@ -257,6 +257,23 @@ RSpec.describe MailPresenter do
           expect(presenter.notification_email_from_chatwoot?).to be(true)
         end
       end
+
+      it 'detects Chatwoot notification emails even when reply_to points to the conversation reply address' do
+        notification_mail = Mail.new do
+          from 'Chatwoot <accounts@chatwoot.com>'
+          reply_to 'reply+5f85d369-8486-41c0-87ce-5a914a00b721@reply.chatwoot.com'
+          to 'Customer <customer@example.com>'
+          header['Subject'] = '[#81209] New messages on this conversation'
+          body 'Thank you for your understanding.'
+        end
+
+        with_modified_env MAILER_SENDER_EMAIL: 'Chatwoot <accounts@chatwoot.com>' do
+          presenter = described_class.new(notification_mail)
+
+          expect(presenter.original_sender).to eq('reply+5f85d369-8486-41c0-87ce-5a914a00b721@reply.chatwoot.com')
+          expect(presenter.notification_email_from_chatwoot?).to be(true)
+        end
+      end
     end
   end
 end