diff --git a/app/jobs/agent_bots/webhook_job.rb b/app/jobs/agent_bots/webhook_job.rb
index b3a3d6cc1..2786ce70e 100644
--- a/app/jobs/agent_bots/webhook_job.rb
+++ b/app/jobs/agent_bots/webhook_job.rb
@@ -1,7 +1,14 @@
 class AgentBots::WebhookJob < WebhookJob
   queue_as :high
+  retry_on RestClient::TooManyRequests, RestClient::InternalServerError, wait: 3.seconds, attempts: 3 do |job, error|
+    url, payload, webhook_type = job.arguments
+    Webhooks::Trigger.new(url, payload, webhook_type || :agent_bot_webhook).handle_failure(error)
+  end
 
   def perform(url, payload, webhook_type = :agent_bot_webhook)
     super(url, payload, webhook_type)
+  rescue RestClient::TooManyRequests, RestClient::InternalServerError => e
+    Rails.logger.warn("[AgentBots::WebhookJob] attempt #{executions} failed #{e.class.name}")
+    raise
   end
 end
diff --git a/lib/webhooks/trigger.rb b/lib/webhooks/trigger.rb
index 456e186ca..7cb15c836 100644
--- a/lib/webhooks/trigger.rb
+++ b/lib/webhooks/trigger.rb
@@ -15,9 +15,17 @@ class Webhooks::Trigger
 
   def execute
     perform_request
+  rescue RestClient::TooManyRequests, RestClient::InternalServerError => e
+    raise if @webhook_type == :agent_bot_webhook
+
+    handle_failure(e)
   rescue StandardError => e
-    handle_error(e)
-    Rails.logger.warn "Exception: Invalid webhook URL #{@url} : #{e.message}"
+    handle_failure(e)
+  end
+
+  def handle_failure(error)
+    handle_error(error)
+    Rails.logger.warn "Exception: Invalid webhook URL #{@url} : #{error.message}"
   end
 
   private
diff --git a/spec/jobs/agent_bots/webhook_job_spec.rb b/spec/jobs/agent_bots/webhook_job_spec.rb
index 346d85e83..c14c46cb3 100644
--- a/spec/jobs/agent_bots/webhook_job_spec.rb
+++ b/spec/jobs/agent_bots/webhook_job_spec.rb
@@ -8,6 +8,16 @@ RSpec.describe AgentBots::WebhookJob do
   let(:url) { 'https://test.com' }
   let(:payload) { { name: 'test' } }
   let(:webhook_type) { :agent_bot_webhook }
+  let(:retryable_error) { RestClient::InternalServerError.new(nil, 500) }
+
+  before do
+    ActiveJob::Base.queue_adapter = :test
+  end
+
+  after do
+    clear_enqueued_jobs
+    clear_performed_jobs
+  end
 
   it 'queues the job' do
     expect { job }.to have_enqueued_job(described_class)
@@ -19,4 +29,23 @@ RSpec.describe AgentBots::WebhookJob do
     expect(Webhooks::Trigger).to receive(:execute).with(url, payload, webhook_type, secret: nil, delivery_id: nil)
     perform_enqueued_jobs { job }
   end
+
+  it 'configures retry handlers for 429 and 500 errors' do
+    handlers = described_class.rescue_handlers.map(&:first)
+
+    expect(handlers).to include('RestClient::TooManyRequests', 'RestClient::InternalServerError')
+  end
+
+  it 'retries 3 times and handles failure after retries are exhausted' do
+    allow(Webhooks::Trigger).to receive(:execute).and_raise(retryable_error)
+    trigger_instance = instance_double(Webhooks::Trigger, handle_failure: true)
+    allow(Webhooks::Trigger).to receive(:new).and_return(trigger_instance)
+    allow(Rails.logger).to receive(:warn)
+
+    expect(Webhooks::Trigger).to receive(:execute).exactly(3).times
+    expect(trigger_instance).to receive(:handle_failure).with(instance_of(RestClient::InternalServerError)).once
+    expect(Rails.logger).to receive(:warn).with(/AgentBots::WebhookJob/).exactly(3).times
+
+    perform_enqueued_jobs { job }
+  end
 end
diff --git a/spec/lib/webhooks/trigger_spec.rb b/spec/lib/webhooks/trigger_spec.rb
index 1e047b557..90d1ce7f8 100644
--- a/spec/lib/webhooks/trigger_spec.rb
+++ b/spec/lib/webhooks/trigger_spec.rb
@@ -77,6 +77,40 @@ describe Webhooks::Trigger do
       let!(:pending_conversation) { create(:conversation, inbox: inbox, status: :pending, account: account) }
       let!(:pending_message) { create(:message, account: account, inbox: inbox, conversation: pending_conversation) }
 
+      it 'raises 500 errors for retry and does not reopen conversation immediately' do
+        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::InternalServerError.new(nil, 500)).once
+
+        expect { trigger.execute(url, payload, webhook_type) }.to raise_error(RestClient::InternalServerError)
+        expect(pending_conversation.reload.status).to eq('pending')
+        expect(Conversations::ActivityMessageJob).not_to have_been_enqueued
+      end
+
+      it 'raises 429 errors for retry and does not reopen conversation immediately' do
+        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::TooManyRequests.new(nil, 429)).once
+
+        expect { trigger.execute(url, payload, webhook_type) }.to raise_error(RestClient::TooManyRequests)
+        expect(pending_conversation.reload.status).to eq('pending')
+        expect(Conversations::ActivityMessageJob).not_to have_been_enqueued
+      end
+
       it 'reopens conversation and enqueues activity message if pending' do
         payload = { event: 'message_created', id: pending_message.id }
 
@@ -166,6 +200,22 @@ describe Webhooks::Trigger do
         expect(activity_message.content).to eq(agent_bot_error_content)
       end
     end
+
+    it 'handles 500 without raising for non-agent webhooks' do
+      payload = { event: 'message_created', conversation: { id: conversation.id }, id: 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::InternalServerError.new(nil, 500)).once
+
+      expect { trigger.execute(url, payload, webhook_type) }.not_to raise_error
+      expect(message.reload.status).to eq('failed')
+    end
   end
 
   describe 'request headers' do