diff --git a/app/models/account.rb b/app/models/account.rb
index fead5f0f7..4816494fb 100644
--- a/app/models/account.rb
+++ b/app/models/account.rb
@@ -40,6 +40,7 @@ class Account < ApplicationRecord
         'auto_resolve_ignore_waiting': { 'type': %w[boolean null] },
         'audio_transcriptions': { 'type': %w[boolean null] },
         'auto_resolve_label': { 'type': %w[string null] },
+        'keep_pending_on_bot_failure': { 'type': %w[boolean null] },
         'conversation_required_attributes': {
           'type': %w[array null],
           'items': { 'type': 'string' }
@@ -88,6 +89,7 @@ class Account < ApplicationRecord
 
   store_accessor :settings, :audio_transcriptions, :auto_resolve_label
   store_accessor :settings, :captain_models, :captain_features
+  store_accessor :settings, :keep_pending_on_bot_failure
 
   has_many :account_users, dependent: :destroy_async
   has_many :agent_bot_inboxes, dependent: :destroy_async
diff --git a/lib/webhooks/trigger.rb b/lib/webhooks/trigger.rb
index 54bd7499d..ef3410b78 100644
--- a/lib/webhooks/trigger.rb
+++ b/lib/webhooks/trigger.rb
@@ -36,16 +36,21 @@ class Webhooks::Trigger
 
     case @webhook_type
     when :agent_bot_webhook
-      conversation = message.conversation
-      return unless conversation&.pending?
-
-      conversation.open!
-      create_agent_bot_error_activity(conversation)
+      update_conversation_status(message)
     when :api_inbox_webhook
       update_message_status(error)
     end
   end
 
+  def update_conversation_status(message)
+    conversation = message.conversation
+    return unless conversation&.pending?
+    return if conversation&.account&.keep_pending_on_bot_failure
+
+    conversation.open!
+    create_agent_bot_error_activity(conversation)
+  end
+
   def create_agent_bot_error_activity(conversation)
     content = I18n.t('conversations.activity.agent_bot.error_moved_to_open')
     Conversations::ActivityMessageJob.perform_later(conversation, activity_message_params(conversation, content))
diff --git a/spec/lib/webhooks/trigger_spec.rb b/spec/lib/webhooks/trigger_spec.rb
index 78bf361c4..79cf92150 100644
--- a/spec/lib/webhooks/trigger_spec.rb
+++ b/spec/lib/webhooks/trigger_spec.rb
@@ -74,10 +74,11 @@ describe Webhooks::Trigger do
 
     context 'when webhook type is agent bot' do
       let(:webhook_type) { :agent_bot_webhook }
+      let!(:pending_conversation) { create(:conversation, inbox: inbox, status: :pending, account: account) }
+      let!(:pending_message) { create(:message, account: account, inbox: inbox, conversation: pending_conversation) }
 
       it 'reopens conversation and enqueues activity message if pending' do
-        conversation.update(status: :pending)
-        payload = { event: 'message_created', conversation: { id: conversation.id }, id: message.id }
+        payload = { event: 'message_created', id: pending_message.id }
 
         expect(RestClient::Request).to receive(:execute)
           .with(
@@ -92,11 +93,11 @@ describe Webhooks::Trigger do
           perform_enqueued_jobs do
             trigger.execute(url, payload, webhook_type)
           end
-        end.not_to(change { message.reload.status })
+        end.not_to(change { pending_message.reload.status })
 
-        expect(conversation.reload.status).to eq('open')
+        expect(pending_conversation.reload.status).to eq('open')
 
-        activity_message = conversation.reload.messages.order(:created_at).last
+        activity_message = pending_conversation.reload.messages.order(:created_at).last
         expect(activity_message.message_type).to eq('activity')
         expect(activity_message.content).to eq(agent_bot_error_content)
       end
@@ -118,9 +119,52 @@ describe Webhooks::Trigger do
         end.not_to(change { message.reload.status })
 
         expect(Conversations::ActivityMessageJob).not_to have_been_enqueued
-
         expect(conversation.reload.status).to eq('open')
       end
+
+      it 'keeps conversation pending when keep_pending_on_bot_failure setting is enabled' do
+        account.update(keep_pending_on_bot_failure: true)
+        payload = { event: 'message_created', id: pending_message.id }
+
+        expect(RestClient::Request).to receive(:execute)
+          .with(
+            method: :post,
+            url: url,
+            payload: payload.to_json,
+            headers: { content_type: :json, accept: :json },
+            timeout: webhook_timeout
+          ).and_raise(RestClient::ExceptionWithResponse.new('error', 500)).once
+
+        trigger.execute(url, payload, webhook_type)
+
+        expect(Conversations::ActivityMessageJob).not_to have_been_enqueued
+        expect(pending_conversation.reload.status).to eq('pending')
+      end
+
+      it 'reopens conversation when keep_pending_on_bot_failure setting is disabled' do
+        account.update(keep_pending_on_bot_failure: false)
+        payload = { event: 'message_created', id: pending_message.id }
+
+        expect(RestClient::Request).to receive(:execute)
+          .with(
+            method: :post,
+            url: url,
+            payload: payload.to_json,
+            headers: { content_type: :json, accept: :json },
+            timeout: webhook_timeout
+          ).and_raise(RestClient::ExceptionWithResponse.new('error', 500)).once
+        expect do
+          perform_enqueued_jobs do
+            trigger.execute(url, payload, webhook_type)
+          end
+        end.not_to(change { pending_message.reload.status })
+
+        expect(pending_conversation.reload.status).to eq('open')
+
+        activity_message = pending_conversation.reload.messages.order(:created_at).last
+        expect(activity_message.message_type).to eq('activity')
+        expect(activity_message.content).to eq(agent_bot_error_content)
+      end
     end
   end