diff --git a/ruby/lib/jam_ruby/app/mailers/user_mailer.rb b/ruby/lib/jam_ruby/app/mailers/user_mailer.rb
index 9cece2313..22b9fdc2e 100644
--- a/ruby/lib/jam_ruby/app/mailers/user_mailer.rb
+++ b/ruby/lib/jam_ruby/app/mailers/user_mailer.rb
@@ -2010,7 +2010,12 @@ module JamRuby
       @session_description = @lesson_session.music_session.description
       @session_date = @lesson_session.slot.pretty_scheduled_start(true)
       @user = @target
-      email = @lesson_session.school_over_teacher
+      if chat_msg.user == chat_msg.lesson_session.student
+        email = @lesson_session.school_over_teacher
+      else
+        email = [chat_msg.lesson_session.student.email]
+      end
+
       @subject = "#{@sender.name} has sent you a message about a lesson"
       unique_args = {:type => "lesson_chat"}
 
diff --git a/ruby/lib/jam_ruby/models/chat_message.rb b/ruby/lib/jam_ruby/models/chat_message.rb
index 1a258e30b..4afa56cc5 100644
--- a/ruby/lib/jam_ruby/models/chat_message.rb
+++ b/ruby/lib/jam_ruby/models/chat_message.rb
@@ -61,9 +61,8 @@ module JamRuby
         lesson_session.save(validate: false)
 
         # a nil purpose means 'normal chat', which is the only time we should send an email
-        if !target.online? && purpose.nil? && message.present?
+        if !target.online? && message.present?
           UserMailer.lesson_chat(chat_msg).deliver_now
-
         end
       end