diff --git a/app/models/bot/smooch.rb b/app/models/bot/smooch.rb
index e85a593db2..4782adbb93 100644
--- a/app/models/bot/smooch.rb
+++ b/app/models/bot/smooch.rb
@@ -1075,7 +1075,7 @@ def self.refresh_smooch_menu_timeout(message, app_id)
     uid = message['authorId']
     time = Time.now.to_f
     Rails.cache.write("smooch:last_message_from_user:#{uid}", time)
-    self.delay_for(15.minutes, { queue: 'smooch' }).timeout_smooch_menu(time, message, app_id, RequestStore.store[:smooch_bot_provider])
+    self.delay_for(5.minutes, { queue: 'smooch' }).timeout_smooch_menu(time, message, app_id, RequestStore.store[:smooch_bot_provider])
   end
 
   def self.timeout_smooch_menu(time, message, app_id, provider)
diff --git a/app/models/concerns/smooch_messages.rb b/app/models/concerns/smooch_messages.rb
index a77a2edf09..c537c59fa9 100644
--- a/app/models/concerns/smooch_messages.rb
+++ b/app/models/concerns/smooch_messages.rb
@@ -286,7 +286,7 @@ def handle_bundle_messages(type, list, last, app_id, annotated, send_message = t
       if ['timeout_requests', 'menu_options_requests', 'resource_requests', 'relevant_search_result_requests', 'timeout_search_requests'].include?(type)
         key = "smooch:banned:#{bundle['authorId']}"
         if Rails.cache.read(key).nil?
-          [annotated].flatten.uniq.each { |a| self.save_message_later(bundle, app_id, type, a) }
+          [annotated].flatten.uniq.each_with_index { |a, i| self.save_message_later(bundle, app_id, type, a, i * 10) }
         end
       end
     end
@@ -317,12 +317,12 @@ def supported_message?(message)
       ret
     end
 
-    def save_message_later(message, app_id, request_type = 'default_requests', annotated = nil)
+    def save_message_later(message, app_id, request_type = 'default_requests', annotated = nil, interval = 0)
       mapping = { 'siege' => 'siege' }
       queue = RequestStore.store[:smooch_bot_queue].to_s
       queue = queue.blank? ? 'smooch' : (mapping[queue] || 'smooch')
       type = (message['type'] == 'text' && !message['text'][/https?:\/\/[^\s]+/, 0].blank?) ? 'link' : message['type']
-      SmoochWorker.set(queue: queue).perform_in(1.second, message.to_json, type, app_id, request_type, YAML.dump(annotated))
+      SmoochWorker.set(queue: queue).perform_in(1.second + interval.seconds, message.to_json, type, app_id, request_type, YAML.dump(annotated))
     end
 
     def default_archived_flag
@@ -370,8 +370,9 @@ def create_smooch_request(annotated, message, app_id, author)
       fields = { smooch_data: message.merge({ app_id: app_id }).to_json }
       result = self.smooch_api_get_messages(app_id, message['authorId'])
       fields[:smooch_conversation_id] = result.conversation.id unless result.nil? || result.conversation.nil?
+      fields[:smooch_message_id] = message['_id']
       self.create_smooch_annotations(annotated, author, fields)
-      # update channel values for ProjectMedia items
+      # Update channel values for ProjectMedia items
       if annotated.class.name == 'ProjectMedia'
         channel_value = self.get_smooch_channel(message)
         unless channel_value.blank?
@@ -407,7 +408,11 @@ def create_smooch_annotations(annotated, author, fields, attach_to = false)
       a.skip_notifications = true
       a.disable_es_callbacks = Rails.env.to_s == 'test'
       a.set_fields = fields.to_json
-      a.save!
+      begin
+        a.save!
+      rescue ActiveRecord::RecordNotUnique
+        # Don't save a duplicate request
+      end
       User.current = current_user
     end
 
diff --git a/app/models/concerns/smooch_search.rb b/app/models/concerns/smooch_search.rb
index 083f000ad0..6774209fc5 100644
--- a/app/models/concerns/smooch_search.rb
+++ b/app/models/concerns/smooch_search.rb
@@ -247,15 +247,16 @@ def send_search_results_to_whatsapp_user(uid, reports, app_id)
       # Expires after the time to give feedback is expired
       Rails.cache.write("smooch:user_search_bundle:#{uid}:#{search_id}", self.list_of_bundled_messages_from_user(uid), expires_in: 20.minutes)
       self.clear_user_bundled_messages(uid)
-      reports.each do |report|
+      reports.each_with_index do |report, i|
         text = report.report_design_text if report.report_design_field_value('use_text_message')
         image_url = report.report_design_image_url if report.report_design_field_value('use_visual_card')
         options = [{
-          value: { project_media_id: report.annotated_id, keyword: 'search_result_is_relevant', search_id: search_id }.to_json,
+          value: { project_media_id: report.annotated_id, keyword: 'search_result_is_relevant', search_id: search_id, index: i }.to_json,
           label: '👍'
         }]
         self.send_message_to_user_with_buttons(uid, text || '-', options, image_url, 'search_result') # "text" is mandatory for WhatsApp interactive messages
-        self.delay_for(15.minutes, { queue: 'smooch_priority' }).timeout_if_no_feedback_is_given_to_search_result(app_id, uid, search_id, report.annotated_id)
+        # Schedule each timeout with some interval between them just to avoid race conditions that could create duplicate media
+        self.delay_for((5 + i).minutes, { queue: 'smooch_priority' }).timeout_if_no_feedback_is_given_to_search_result(app_id, uid, search_id, report.annotated_id)
       end
     end
 
@@ -313,8 +314,10 @@ def search_result_button_click_callback(message, uid, app_id, workflow, language
       result = ProjectMedia.find(payload['project_media_id'])
       bundle = Rails.cache.read("smooch:user_search_bundle:#{uid}:#{payload['search_id']}").to_a
       unless bundle.empty?
+        # Give some interval just to avoid race conditions if the user gives feedback too fast
+        interval = payload['index'].to_i * 10
         Rails.cache.write("smooch:user_search_bundle:#{uid}:#{payload['search_id']}:#{result.id}", Time.now.to_i) # Store that the user has given feedback to this search result
-        self.delay_for(1.seconds, { queue: 'smooch', retry: false }).bundle_messages(uid, message['_id'], app_id, 'relevant_search_result_requests', [result], true, bundle)
+        self.delay_for((interval + 1).seconds, { queue: 'smooch', retry: false }).bundle_messages(uid, message['_id'], app_id, 'relevant_search_result_requests', [result], true, bundle)
         self.send_final_message_to_user(uid, self.get_custom_string('search_result_is_relevant', language), workflow, language)
       end
     end
diff --git a/db/migrate/20231026162554_add_smooch_message_id_field.rb b/db/migrate/20231026162554_add_smooch_message_id_field.rb
new file mode 100644
index 0000000000..0d4fb0f6bd
--- /dev/null
+++ b/db/migrate/20231026162554_add_smooch_message_id_field.rb
@@ -0,0 +1,11 @@
+class AddSmoochMessageIdField < ActiveRecord::Migration[6.1]
+  require 'sample_data'
+  include SampleData
+
+  def change
+    at = DynamicAnnotation::AnnotationType.where(annotation_type: 'smooch').last
+    ft = DynamicAnnotation::FieldType.where(field_type: 'text').last || create_field_type(field_type: 'text', label: 'Text')
+    create_field_instance annotation_type_object: at, name: 'smooch_message_id', label: 'Message Id', field_type_object: ft, optional: true
+    execute %{CREATE UNIQUE INDEX smooch_request_message_id_unique_id ON dynamic_annotation_fields (value) WHERE field_name = 'smooch_message_id' AND value <> '' AND value <> '""'}
+  end
+end