diff --git a/app/controllers/api/v1/accounts/automation_rules_controller.rb b/app/controllers/api/v1/accounts/automation_rules_controller.rb
index e1e5ddbad..dc4f7b6c8 100644
--- a/app/controllers/api/v1/accounts/automation_rules_controller.rb
+++ b/app/controllers/api/v1/accounts/automation_rules_controller.rb
@@ -7,14 +7,22 @@ class Api::V1::Accounts::AutomationRulesController < Api::V1::Accounts::BaseCont
   end
 
   def create
-    @automation_rule = Current.account.automation_rules.create(automation_rules_permit)
-    @automation_rule.update(actions: params[:actions])
+    @automation_rule = Current.account.automation_rules.new(automation_rules_permit)
+    @automation_rule.actions = params[:actions]
+
+    render json: { error: @automation_rule.errors.messages }, status: :unprocessable_entity and return unless @automation_rule.valid?
+
+    @automation_rule.save!
+    process_attachments
+    @automation_rule
   end
 
   def show; end
 
   def update
     @automation_rule.update(automation_rules_permit)
+    process_attachments
+    @automation_rule
   end
 
   def destroy
@@ -31,6 +39,14 @@ class Api::V1::Accounts::AutomationRulesController < Api::V1::Accounts::BaseCont
 
   private
 
+  def process_attachments
+    return if params[:attachments].blank?
+
+    params[:attachments].each do |uploaded_attachment|
+      @automation_rule.files.attach(uploaded_attachment)
+    end
+  end
+
   def automation_rules_permit
     params.permit(
       :name, :description, :event_name, :account_id, :active,
diff --git a/app/models/automation_rule.rb b/app/models/automation_rule.rb
index 0d25a2786..b0b62eef9 100644
--- a/app/models/automation_rule.rb
+++ b/app/models/automation_rule.rb
@@ -19,6 +19,7 @@
 #
 class AutomationRule < ApplicationRecord
   belongs_to :account
+  has_many_attached :files
 
   validate :json_conditions_format
   validate :json_actions_format
@@ -26,8 +27,8 @@ class AutomationRule < ApplicationRecord
 
   scope :active, -> { where(active: true) }
 
-  CONDITIONS_ATTRS = %w[country_code status browser_language assignee_id team_id referer].freeze
-  ACTIONS_ATTRS = %w[send_message add_label send_email_to_team assign_team assign_best_agents].freeze
+  CONDITIONS_ATTRS = %w[email country_code status message_type browser_language assignee_id team_id referer city company].freeze
+  ACTIONS_ATTRS = %w[send_message add_label send_email_to_team assign_team assign_best_agents send_attachments].freeze
 
   private
 
@@ -35,13 +36,17 @@ class AutomationRule < ApplicationRecord
     return if conditions.nil?
 
     attributes = conditions.map { |obj, _| obj['attribute_key'] }
-    (attributes - CONDITIONS_ATTRS).blank?
+    conditions = attributes - CONDITIONS_ATTRS
+    conditions -= account.custom_attribute_definitions.pluck(:attribute_key)
+    errors.add(:conditions, "Automation conditions #{conditions.join(',')} not supported.") if conditions.any?
   end
 
   def json_actions_format
     return if actions.nil?
 
     attributes = actions.map { |obj, _| obj['attribute_key'] }
-    (attributes - ACTIONS_ATTRS).blank?
+    actions = attributes - ACTIONS_ATTRS
+
+    errors.add(:actions, "Automation actions #{actions.join(',')} not supported.") if actions.any?
   end
 end
diff --git a/app/services/automation_rules/action_service.rb b/app/services/automation_rules/action_service.rb
index 3848e30f5..75b1f0474 100644
--- a/app/services/automation_rules/action_service.rb
+++ b/app/services/automation_rules/action_service.rb
@@ -21,6 +21,15 @@ class AutomationRules::ActionService
 
   private
 
+  def send_attachments(_file_params)
+    return if @rule.event_name == 'message_created'
+
+    blobs = @rule.files.map { |file, _| file.blob }
+    params = { content: nil, private: false, attachments: blobs }
+    mb = Messages::MessageBuilder.new(nil, @conversation, params)
+    mb.perform
+  end
+
   def send_email_transcript(emails)
     emails.each do |email|
       ConversationReplyMailer.with(account: @conversation.account).conversation_transcript(@conversation, email)&.deliver_later
@@ -48,7 +57,7 @@ class AutomationRules::ActionService
     return if @rule.event_name == 'message_created'
 
     params = { content: message[0], private: false }
-    mb = Messages::MessageBuilder.new(@administrator, @conversation, params)
+    mb = Messages::MessageBuilder.new(nil, @conversation, params)
     mb.perform
   end
 
@@ -85,10 +94,6 @@ class AutomationRules::ActionService
     end
   end
 
-  def administrator
-    @administrator ||= @account.administrators.first
-  end
-
   def agent_belongs_to_account?(agent_ids)
     @account.agents.pluck(:id).include?(agent_ids[0])
   end
diff --git a/spec/controllers/api/v1/accounts/automation_rules_controller_spec.rb b/spec/controllers/api/v1/accounts/automation_rules_controller_spec.rb
index 5755bf95a..0d3b3e784 100644
--- a/spec/controllers/api/v1/accounts/automation_rules_controller_spec.rb
+++ b/spec/controllers/api/v1/accounts/automation_rules_controller_spec.rb
@@ -84,6 +84,23 @@ RSpec.describe 'Api::V1::Accounts::AutomationRulesController', type: :request do
         }.with_indifferent_access
       end
 
+      it 'throws an error for unknown attributes in condtions' do
+        expect(account.automation_rules.count).to eq(0)
+        params[:conditions] << {
+          attribute_key: 'unknown_attribute',
+          filter_operator: 'equal_to',
+          values: ['en'],
+          query_operator: 'AND'
+        }
+
+        post "/api/v1/accounts/#{account.id}/automation_rules",
+             headers: administrator.create_new_auth_token,
+             params: params
+
+        expect(response).to have_http_status(:unprocessable_entity)
+        expect(account.automation_rules.count).to eq(0)
+      end
+
       it 'Saves for automation_rules for account with country_code and browser_language conditions' do
         expect(account.automation_rules.count).to eq(0)
 
@@ -113,6 +130,67 @@ RSpec.describe 'Api::V1::Accounts::AutomationRulesController', type: :request do
         expect(response).to have_http_status(:success)
         expect(account.automation_rules.count).to eq(1)
       end
+
+      it 'Saves file in the automation actions to send an attachments' do
+        file = fixture_file_upload(Rails.root.join('spec/assets/avatar.png'), 'image/png')
+        params[:attachments] = [file]
+        params[:actions] = [
+          {
+            action_name: :send_message,
+            action_params: ['Welcome to the chatwoot platform.']
+          },
+          {
+            action_name: :update_additional_attributes,
+            action_params: [{ intiated_at: '2021-12-03 17:25:26.844536 +0530' }]
+          },
+          {
+            action_name: :send_attachments
+          }
+        ]
+
+        expect(account.automation_rules.count).to eq(0)
+
+        post "/api/v1/accounts/#{account.id}/automation_rules",
+             headers: administrator.create_new_auth_token,
+             params: params
+
+        expect(response).to have_http_status(:success)
+        expect(account.automation_rules.count).to eq(1)
+        automation_rule = account.automation_rules.first
+        expect(automation_rule.files.presence).to be_truthy
+        expect(automation_rule.files.count).to eq(1)
+      end
+
+      it 'Saves files in the automation actions to send multiple attachments' do
+        file_1 = fixture_file_upload(Rails.root.join('spec/assets/avatar.png'), 'image/png')
+        file_2 = fixture_file_upload(Rails.root.join('spec/assets/sample.pdf'), 'image/png')
+        params[:attachments] = [file_1, file_2]
+        params[:actions] = [
+          {
+            action_name: :send_message,
+            action_params: ['Welcome to the chatwoot platform.']
+          },
+          {
+            action_name: :update_additional_attributes,
+            action_params: [{ intiated_at: '2021-12-03 17:25:26.844536 +0530' }]
+          },
+          {
+            action_name: :send_attachments
+          }
+        ]
+
+        expect(account.automation_rules.count).to eq(0)
+
+        post "/api/v1/accounts/#{account.id}/automation_rules",
+             headers: administrator.create_new_auth_token,
+             params: params
+
+        expect(response).to have_http_status(:success)
+        expect(account.automation_rules.count).to eq(1)
+        automation_rule = account.automation_rules.first
+        expect(automation_rule.files.presence).to be_truthy
+        expect(automation_rule.files.count).to eq(2)
+      end
     end
   end
 
diff --git a/spec/listeners/automation_rule_listener_spec.rb b/spec/listeners/automation_rule_listener_spec.rb
index bf015fab3..6c4fc0c2a 100644
--- a/spec/listeners/automation_rule_listener_spec.rb
+++ b/spec/listeners/automation_rule_listener_spec.rb
@@ -42,8 +42,12 @@ describe AutomationRuleListener do
                                         { 'action_name' => 'send_email_transcript', 'action_params' => 'new_agent@example.com' },
                                         { 'action_name' => 'mute_conversation', 'action_params' => nil },
                                         { 'action_name' => 'change_status', 'action_params' => ['snoozed'] },
-                                        { 'action_name' => 'send_message', 'action_params' => ['Send this message.'] }
+                                        { 'action_name' => 'send_message', 'action_params' => ['Send this message.'] },
+                                        { 'action_name' => 'send_attachments' }
                                       ])
+    file = fixture_file_upload(Rails.root.join('spec/assets/avatar.png'), 'image/png')
+    automation_rule.files.attach(file)
+    automation_rule.save
   end
 
   describe '#conversation_status_changed' do
@@ -112,7 +116,7 @@ describe AutomationRuleListener do
 
         conversation.reload
 
-        expect(conversation.messages.last.content).to eq('Send this message.')
+        expect(conversation.messages.first.content).to eq('Send this message.')
       end
 
       it 'triggers automation rule changes status to snoozed' do
@@ -150,6 +154,18 @@ describe AutomationRuleListener do
 
         listener.conversation_status_changed(event)
       end
+
+      it 'triggers automation rule send attachments in messages' do
+        automation_rule
+
+        expect(TeamNotifications::AutomationNotificationMailer).to receive(:conversation_creation)
+
+        listener.conversation_status_changed(event)
+
+        conversation.reload
+
+        expect(conversation.messages.last.attachments.count).to eq(1)
+      end
     end
   end
 
@@ -225,7 +241,7 @@ describe AutomationRuleListener do
 
         conversation.reload
 
-        expect(conversation.messages.last.content).to eq('Send this message.')
+        expect(conversation.messages.first.content).to eq('Send this message.')
       end
 
       it 'triggers automation_rule with contact standard attributes' do
@@ -333,7 +349,7 @@ describe AutomationRuleListener do
 
         conversation.reload
 
-        expect(conversation.messages.last.content).to eq('Send this message.')
+        expect(conversation.messages.first.content).to eq('Send this message.')
       end
     end
   end