diff --git a/app/assets/javascripts/app/controllers/_ui_element/ticket_perform_action.coffee b/app/assets/javascripts/app/controllers/_ui_element/ticket_perform_action.coffee
index bd7b04dc5..fa8a00d79 100644
--- a/app/assets/javascripts/app/controllers/_ui_element/ticket_perform_action.coffee
+++ b/app/assets/javascripts/app/controllers/_ui_element/ticket_perform_action.coffee
@@ -304,18 +304,31 @@ class App.UiElement.ticket_perform_action
     return if elementRow.find('.js-setNotification .js-body').get(0)
 
     options =
+      'article_last_sender': 'Article Last Sender'
       'ticket_owner': 'Owner'
       'ticket_customer': 'Customer'
       'ticket_agents': 'All Agents'
 
     name = "#{attribute.name}::notification.email"
 
-    selection = $("<select class=\"form-control\" name=\"#{name}::recipient\" ></select>")
+    # meta.recipient was a string in the past (single-select) so we convert it to array if needed
+    if !_.isArray(meta.recipient)
+      meta.recipient = [meta.recipient]
+
+    column_select_options = []
     for key, value of options
-      selected = ''
-      if key is meta.recipient
-        selected = 'selected="selected"'
-      selection.append("<option value=\"#{key}\" #{selected}>#{App.i18n.translateInline(value)}</option>")
+      selected = undefined
+      for recipient in meta.recipient
+        if key is recipient
+          selected = true
+      column_select_options.push({ value: key, name: App.i18n.translateInline(value), selected: selected })
+
+    column_select = new App.ColumnSelect
+      attribute:
+        name:    "#{name}::recipient"
+        options: column_select_options
+
+    selection = column_select.element()
 
     notificationElement = $( App.view('generic/ticket_perform_action/notification_email')(
       attribute: attribute
diff --git a/app/models/ticket.rb b/app/models/ticket.rb
index 863338ca8..f529c3c93 100644
--- a/app/models/ticket.rb
+++ b/app/models/ticket.rb
@@ -745,53 +745,87 @@ perform changes on ticket
 
       # send notification
       if object_name == 'notification'
-        recipients = []
-        if value['recipient'] == 'ticket_customer'
-          recipients.push User.lookup(id: customer_id)
-        elsif value['recipient'] == 'ticket_owner'
-          recipients.push User.lookup(id: owner_id)
-        elsif value['recipient'] == 'ticket_agents'
-          recipients = recipients.concat(agent_of_group)
-        else
-          logger.error "Unknown email notification recipient '#{value['recipient']}'"
-          next
+
+        # value['recipient'] was a string in the past (single-select) so we convert it to array if needed
+        value_recipient = value['recipient']
+        if !value_recipient.is_a?(Array)
+          value_recipient = [value_recipient]
         end
-        recipient_string = ''
-        recipient_already = {}
-        recipients.each { |user|
+
+        recipients_raw = []
+        value_recipient.each { |recipient|
+          if recipient == 'article_last_sender'
+            if item && item[:article_id]
+              article = Ticket::Article.lookup(id: item[:article_id])
+              if article.reply_to.present?
+                recipients_raw.push(article.reply_to)
+              elsif article.from.present?
+                recipients_raw.push(article.from)
+              elsif article.origin_by_id
+                email = User.lookup(id: article.origin_by_id).email
+                recipients_raw.push(email)
+              elsif article.created_by_id
+                email = User.lookup(id: article.created_by_id).email
+                recipients_raw.push(email)
+              end
+            end
+          elsif recipient == 'ticket_customer'
+            email = User.lookup(id: customer_id).email
+            recipients_raw.push(email)
+          elsif recipient == 'ticket_owner'
+            email = User.lookup(id: owner_id).email
+            recipients_raw.push(email)
+          elsif recipient == 'ticket_agents'
+            agent_of_group.each { |user|
+              recipients_raw.push(user.email)
+            }
+          else
+            logger.error "Unknown email notification recipient '#{recipient}'"
+            next
+          end
+        }
+
+        recipients_checked = []
+        recipients_raw.each { |recipient_email|
 
           # send notifications only to email adresses
-          next if !user.email
-          next if user.email !~ /@/
+          next if !recipient_email
+          next if recipient_email !~ /@/
+
+          # check if address is valid
+          begin
+            recipient_email = Mail::Address.new(recipient_email).address
+          rescue
+            next # because unable to parse
+          end
 
           # do not sent notifications to this recipients
           send_no_auto_response_reg_exp = Setting.get('send_no_auto_response_reg_exp')
           begin
-            next if user.email =~ /#{send_no_auto_response_reg_exp}/i
+            next if recipient_email =~ /#{send_no_auto_response_reg_exp}/i
           rescue => e
             logger.error "ERROR: Invalid regex '#{send_no_auto_response_reg_exp}' in setting send_no_auto_response_reg_exp"
             logger.error 'ERROR: ' + e.inspect
-            next if user.email =~ /(mailer-daemon|postmaster|abuse|root)@.+?\..+?/i
+            next if recipient_email =~ /(mailer-daemon|postmaster|abuse|root)@.+?\..+?/i
           end
 
           # check if notification should be send because of customer emails
           if item && item[:article_id]
             article = Ticket::Article.lookup(id: item[:article_id])
-            if article && article.preferences['is-auto-response'] == true && article.from && article.from =~ /#{Regexp.quote(user.email)}/i
-              logger.info "Send not trigger based notification to #{user.email} because of auto response tagged incoming email"
+            if article && article.preferences['is-auto-response'] == true && article.from && article.from =~ /#{Regexp.quote(recipient_email)}/i
+              logger.info "Send not trigger based notification to #{recipient_email} because of auto response tagged incoming email"
               next
             end
           end
 
-          email = user.email.downcase.strip
-          next if recipient_already[email]
-          recipient_already[email] = true
-          if recipient_string != ''
-            recipient_string += ', '
-          end
-          recipient_string += email
+          email = recipient_email.downcase.strip
+          next if recipients_checked.include?(email)
+          recipients_checked.push(email)
         }
-        next if recipient_string == ''
+
+        next if recipients_checked.blank?
+        recipient_string = recipients_checked.join(', ')
+
         group = self.group
         next if !group
         email_address = group.email_address
@@ -808,8 +842,6 @@ perform changes on ticket
         objects = {
           ticket: self,
           article: articles.last,
-          #recipient: user,
-          #changes: changes,
         }
 
         # get subject
diff --git a/test/unit/ticket_trigger_test.rb b/test/unit/ticket_trigger_test.rb
index 3bf16da4e..05343af10 100644
--- a/test/unit/ticket_trigger_test.rb
+++ b/test/unit/ticket_trigger_test.rb
@@ -2471,4 +2471,378 @@ class TicketTriggerTest < ActiveSupport::TestCase
     }
   end
 
+  test 'article_last_sender trigger -> reply_to' do
+    trigger = Trigger.create_or_update(
+      name: 'auto reply',
+      condition: {
+        'ticket.action' => {
+          'operator' => 'is',
+          'value' => 'create',
+        },
+        'ticket.state_id' => {
+          'operator' => 'is',
+          'value' => Ticket::State.lookup(name: 'new').id.to_s,
+        }
+      },
+      perform: {
+        'notification.email' => {
+          'body' => 'some text<br>#{ticket.customer.lastname}<br>#{ticket.title}<br>#{article.body}',
+          'recipient' => 'article_last_sender',
+          'subject' => 'Thanks for your inquiry (#{ticket.title})!',
+        },
+      },
+      disable_notification: true,
+      active: true,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+    ticket1 = Ticket.create(
+      title: "some <b>title</b>\n äöüß",
+      group: Group.lookup(name: 'Users'),
+      customer: User.lookup(email: 'nicole.braun@zammad.org'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    Ticket::Article.create(
+      ticket_id: ticket1.id,
+      from: 'some_sender@example.com',
+      to: 'some_recipient+from@example.com',
+      reply_to: 'some_recipient+reply_to@example.com',
+      subject: 'some subject',
+      message_id: 'some@id',
+      body: "some message <b>note</b>\nnew line",
+      internal: false,
+      sender: Ticket::Article::Sender.find_by(name: 'Agent'),
+      type: Ticket::Article::Type.find_by(name: 'note'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+
+    Observer::Transaction.commit
+
+    ticket1.reload
+    assert_equal('new', ticket1.state.name, 'ticket1.state new')
+    assert_equal(2, ticket1.articles.count, 'ticket1.articles verify')
+    auto_response = ticket1.articles.last
+    assert_match('Zammad <zammad@localhost>', auto_response.from)
+    assert_match('some_recipient+reply_to@example.com', auto_response.to)
+  end
+
+  test 'article_last_sender trigger -> from' do
+    trigger = Trigger.create_or_update(
+      name: 'auto reply',
+      condition: {
+        'ticket.action' => {
+          'operator' => 'is',
+          'value' => 'create',
+        },
+        'ticket.state_id' => {
+          'operator' => 'is',
+          'value' => Ticket::State.lookup(name: 'new').id.to_s,
+        }
+      },
+      perform: {
+        'notification.email' => {
+          'body' => 'some text<br>#{ticket.customer.lastname}<br>#{ticket.title}<br>#{article.body}',
+          'recipient' => 'article_last_sender',
+          'subject' => 'Thanks for your inquiry (#{ticket.title})!',
+        },
+      },
+      disable_notification: true,
+      active: true,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+    ticket1 = Ticket.create(
+      title: "some <b>title</b>\n äöüß",
+      group: Group.lookup(name: 'Users'),
+      customer: User.lookup(email: 'nicole.braun@zammad.org'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    Ticket::Article.create(
+      ticket_id: ticket1.id,
+      from: 'some_sender+from@example.com',
+      to: 'some_recipient@example.com',
+      subject: 'some subject',
+      message_id: 'some@id',
+      body: "some message <b>note</b>\nnew line",
+      internal: false,
+      sender: Ticket::Article::Sender.find_by(name: 'Customer'),
+      type: Ticket::Article::Type.find_by(name: 'email'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+
+    Observer::Transaction.commit
+
+    ticket1.reload
+    assert_equal('new', ticket1.state.name, 'ticket1.state new')
+    assert_equal(2, ticket1.articles.count, 'ticket1.articles verify')
+    auto_response = ticket1.articles.last
+    assert_match('Zammad <zammad@localhost>', auto_response.from)
+    assert_match('some_sender+from@example.com', auto_response.to)
+  end
+
+  test 'article_last_sender trigger -> origin_by_id' do
+    trigger = Trigger.create_or_update(
+      name: 'auto reply',
+      condition: {
+        'ticket.action' => {
+          'operator' => 'is',
+          'value' => 'create',
+        },
+        'ticket.state_id' => {
+          'operator' => 'is',
+          'value' => Ticket::State.lookup(name: 'new').id.to_s,
+        }
+      },
+      perform: {
+        'notification.email' => {
+          'body' => 'some text<br>#{ticket.customer.lastname}<br>#{ticket.title}<br>#{article.body}',
+          'recipient' => 'article_last_sender',
+          'subject' => 'Thanks for your inquiry (#{ticket.title})!',
+        },
+      },
+      disable_notification: true,
+      active: true,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+    roles = Role.where(name: 'Customer')
+    customer1 = User.create_or_update(
+      login: 'customer+origin_by_id@example.com',
+      firstname: 'Trigger',
+      lastname: 'Customer1',
+      email: 'customer+origin_by_id@example.com',
+      password: 'customerpw',
+      active: true,
+      roles: roles,
+      updated_at: '2015-02-05 16:37:00',
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    ticket1 = Ticket.create(
+      title: "some <b>title</b>\n äöüß",
+      group: Group.lookup(name: 'Users'),
+      customer: User.lookup(email: 'nicole.braun@zammad.org'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    Ticket::Article.create(
+      ticket_id: ticket1.id,
+      to: 'some_recipient@example.com',
+      subject: 'some subject',
+      message_id: 'some@id',
+      body: "some message <b>note</b>\nnew line",
+      internal: false,
+      sender: Ticket::Article::Sender.find_by(name: 'Customer'),
+      type: Ticket::Article::Type.find_by(name: 'email'),
+      origin_by_id: customer1.id,
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+
+    Observer::Transaction.commit
+
+    ticket1.reload
+    assert_equal('new', ticket1.state.name, 'ticket1.state new')
+    assert_equal(2, ticket1.articles.count, 'ticket1.articles verify')
+    auto_response = ticket1.articles.last
+    assert_match('Zammad <zammad@localhost>', auto_response.from)
+    assert_match('customer+origin_by_id@example.com', auto_response.to)
+  end
+
+  test 'article_last_sender trigger -> created_by_id' do
+    trigger = Trigger.create_or_update(
+      name: 'auto reply',
+      condition: {
+        'ticket.action' => {
+          'operator' => 'is',
+          'value' => 'create',
+        },
+        'ticket.state_id' => {
+          'operator' => 'is',
+          'value' => Ticket::State.lookup(name: 'new').id.to_s,
+        }
+      },
+      perform: {
+        'notification.email' => {
+          'body' => 'some text<br>#{ticket.customer.lastname}<br>#{ticket.title}<br>#{article.body}',
+          'recipient' => 'article_last_sender',
+          'subject' => 'Thanks for your inquiry (#{ticket.title})!',
+        },
+      },
+      disable_notification: true,
+      active: true,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+    roles = Role.where(name: 'Customer')
+    customer1 = User.create_or_update(
+      login: 'customer+created_by_id@example.com',
+      firstname: 'Trigger',
+      lastname: 'Customer1',
+      email: 'customer+created_by_id@example.com',
+      password: 'customerpw',
+      active: true,
+      roles: roles,
+      updated_at: '2015-02-05 16:37:00',
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    ticket1 = Ticket.create(
+      title: "some <b>title</b>\n äöüß",
+      group: Group.lookup(name: 'Users'),
+      customer: User.lookup(email: 'nicole.braun@zammad.org'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    Ticket::Article.create(
+      ticket_id: ticket1.id,
+      to: 'some_recipient@example.com',
+      subject: 'some subject',
+      message_id: 'some@id',
+      body: "some message <b>note</b>\nnew line",
+      internal: false,
+      sender: Ticket::Article::Sender.find_by(name: 'Customer'),
+      type: Ticket::Article::Type.find_by(name: 'email'),
+      updated_by_id: customer1.id,
+      created_by_id: customer1.id,
+    )
+
+    Observer::Transaction.commit
+
+    ticket1.reload
+    assert_equal('new', ticket1.state.name, 'ticket1.state new')
+    assert_equal(2, ticket1.articles.count, 'ticket1.articles verify')
+    auto_response = ticket1.articles.last
+    assert_match('Zammad <zammad@localhost>', auto_response.from)
+    assert_match('customer+created_by_id@example.com', auto_response.to)
+  end
+
+  test 'multiple recipients owner_id, article_last_sender(reply_to) trigger' do
+    trigger = Trigger.create_or_update(
+      name: 'auto reply',
+      condition: {
+        'ticket.action' => {
+          'operator' => 'is',
+          'value' => 'create',
+        },
+        'ticket.state_id' => {
+          'operator' => 'is',
+          'value' => Ticket::State.lookup(name: 'new').id.to_s,
+        }
+      },
+      perform: {
+        'notification.email' => {
+          'body' => 'some text<br>#{ticket.customer.lastname}<br>#{ticket.title}<br>#{article.body}',
+          'recipient' => %w(ticket_owner article_last_sender),
+          'subject' => 'Thanks for your inquiry (#{ticket.title})!',
+        },
+      },
+      disable_notification: true,
+      active: true,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+    admin = User.create_or_update(
+      login: 'admin+owner_recipient@example.com',
+      firstname: 'Role',
+      lastname: "Admin#{name}",
+      email: 'admin+owner_recipient@example.com',
+      password: 'adminpw',
+      active: true,
+      roles: Role.where(name: %w(Admin Agent)),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    ticket1 = Ticket.create(
+      title: "some <b>title</b>\n äöüß",
+      group: Group.lookup(name: 'Users'),
+      customer: User.lookup(email: 'nicole.braun@zammad.org'),
+      owner_id: admin.id,
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    Ticket::Article.create(
+      ticket_id: ticket1.id,
+      from: 'some_sender@example.com',
+      to: 'some_recipient+from@example.com',
+      reply_to: 'some_recipient+reply_to@example.com',
+      subject: 'some subject',
+      message_id: 'some@id',
+      body: "some message <b>note</b>\nnew line",
+      internal: false,
+      sender: Ticket::Article::Sender.find_by(name: 'Agent'),
+      type: Ticket::Article::Type.find_by(name: 'note'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+
+    Observer::Transaction.commit
+
+    ticket1.reload
+    assert_equal('new', ticket1.state.name, 'ticket1.state new')
+    assert_equal(2, ticket1.articles.count, 'ticket1.articles verify')
+    auto_response = ticket1.articles.last
+    assert_match('Zammad <zammad@localhost>', auto_response.from)
+    assert_match('some_recipient+reply_to@example.com', auto_response.to)
+    assert_match('admin+owner_recipient@example.com', auto_response.to)
+  end
+
+  test 'article_last_sender trigger -> invalid reply_to' do
+    trigger = Trigger.create_or_update(
+      name: 'auto reply',
+      condition: {
+        'ticket.action' => {
+          'operator' => 'is',
+          'value' => 'create',
+        },
+        'ticket.state_id' => {
+          'operator' => 'is',
+          'value' => Ticket::State.lookup(name: 'new').id.to_s,
+        }
+      },
+      perform: {
+        'notification.email' => {
+          'body' => 'some text<br>#{ticket.customer.lastname}<br>#{ticket.title}<br>#{article.body}',
+          'recipient' => 'article_last_sender',
+          'subject' => 'Thanks for your inquiry (#{ticket.title})!',
+        },
+      },
+      disable_notification: true,
+      active: true,
+      created_by_id: 1,
+      updated_by_id: 1,
+    )
+    ticket1 = Ticket.create(
+      title: "some <b>title</b>\n äöüß",
+      group: Group.lookup(name: 'Users'),
+      customer: User.lookup(email: 'nicole.braun@zammad.org'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+    Ticket::Article.create(
+      ticket_id: ticket1.id,
+      from: 'some_sender@example.com',
+      to: 'some_recipient+from@example.com',
+      reply_to: 'Blub blub blub some_recipient+reply_to@example',
+      subject: 'some subject',
+      message_id: 'some@id',
+      body: "some message <b>note</b>\nnew line",
+      internal: false,
+      sender: Ticket::Article::Sender.find_by(name: 'Agent'),
+      type: Ticket::Article::Type.find_by(name: 'note'),
+      updated_by_id: 1,
+      created_by_id: 1,
+    )
+
+    Observer::Transaction.commit
+
+    ticket1.reload
+    assert_equal('new', ticket1.state.name, 'ticket1.state new')
+    assert_equal(1, ticket1.articles.count, 'ticket1.articles verify')
+  end
+
 end