diff --git a/omnibus/files/server-ctl-cookbooks/infra-server/recipes/opensearch.rb b/omnibus/files/server-ctl-cookbooks/infra-server/recipes/opensearch.rb
index f1af32313e..3b53521fda 100644
--- a/omnibus/files/server-ctl-cookbooks/infra-server/recipes/opensearch.rb
+++ b/omnibus/files/server-ctl-cookbooks/infra-server/recipes/opensearch.rb
@@ -1,5 +1,12 @@
 # Copyright:: Chef Software, Inc.
 # All Rights Reserved
+#
+# OpenSearch Recipe - Enhanced with Smart Readiness Checking
+#
+# This recipe configures OpenSearch for Chef Server with intelligent
+# startup validation instead of hardcoded sleep timings. The enhancement
+# addresses CHEF-26134 timing issues that emerged with OpenSearch 1.3.20
+# by implementing proper health checks before security configuration.
 
 MAX_MAP_COUNT = 262_144
 cluster_name = if node['previous_run'] && node['previous_run']['opensearch'] && node['previous_run']['opensearch']['cluster_name']
@@ -177,14 +184,101 @@
   retry_delay 1
 end
 
-chef_sleep 10
+# Smart OpenSearch readiness check instead of hardcoded sleep
+ruby_block 'wait_for_opensearch_ready' do
+  block do
+    require 'net/http'
+    require 'json'
+    require 'timeout'
+
+    max_attempts = 60 # Maximum 5 minutes (60 * 5 seconds)
+    attempt = 0
+    opensearch_ready = false
+    opensearch_port = node['private_chef']['opensearch']['port'] || 9200
+
+    Chef::Log.info("Waiting for OpenSearch to become ready on port #{opensearch_port}...")
+
+    while attempt < max_attempts && !opensearch_ready
+      attempt += 1
+
+      begin
+        Timeout.timeout(10) do
+          # Check if OpenSearch API is responding
+          uri = URI("http://localhost:#{opensearch_port}/")
+          http = Net::HTTP.new(uri.host, uri.port)
+          http.read_timeout = 5
+          http.open_timeout = 5
+
+          request = Net::HTTP::Get.new(uri)
+          response = http.request(request)
+
+          if response.code == '200' || response.code == '401'
+            # 200 = OK, 401 = Unauthorized but service is running
+            begin
+              # Additional check: verify cluster health
+              health_uri = URI("http://localhost:#{opensearch_port}/_cluster/health")
+              health_request = Net::HTTP::Get.new(health_uri)
+              health_response = http.request(health_request)
+
+              if health_response.code == '200'
+                health_data = JSON.parse(health_response.body)
+                cluster_status = health_data['status']
+
+                if %w(green yellow).include?(cluster_status)
+                  Chef::Log.info("OpenSearch is ready! Cluster status: #{cluster_status}, attempt #{attempt}/#{max_attempts}")
+                  opensearch_ready = true
+                else
+                  Chef::Log.debug("OpenSearch cluster status is #{cluster_status}, waiting... (attempt #{attempt}/#{max_attempts})")
+                end
+              elsif health_response.code == '401'
+                # Security is enabled but service is responding - we can proceed
+                Chef::Log.info("OpenSearch is ready! Security enabled, attempt #{attempt}/#{max_attempts}")
+                opensearch_ready = true
+              else
+                Chef::Log.debug("OpenSearch cluster health check failed with code #{health_response.code}, waiting... (attempt #{attempt}/#{max_attempts})")
+              end
+            rescue JSON::ParserError => e
+              Chef::Log.debug("Error checking cluster health: #{e.message}, but basic service is responding")
+              # If health check fails but basic service responds, consider it ready
+              opensearch_ready = true
+            rescue StandardError => e
+              Chef::Log.debug("Error checking cluster health: #{e.message}, but basic service is responding")
+              # If health check fails but basic service responds, consider it ready
+              opensearch_ready = true
+            end
+          else
+            Chef::Log.debug("OpenSearch not ready, HTTP response code: #{response.code} (attempt #{attempt}/#{max_attempts})")
+          end
+        end
+      rescue Timeout::Error
+        Chef::Log.debug("Timeout connecting to OpenSearch (attempt #{attempt}/#{max_attempts})")
+      rescue Errno::ECONNREFUSED, Errno::EHOSTUNREACH, SocketError => e
+        Chef::Log.debug("Connection failed to OpenSearch: #{e.message} (attempt #{attempt}/#{max_attempts})")
+      rescue StandardError => e
+        Chef::Log.debug("Unexpected error checking OpenSearch: #{e.message} (attempt #{attempt}/#{max_attempts})")
+      end
+
+      unless opensearch_ready
+        if attempt < max_attempts
+          Chef::Log.debug('OpenSearch not ready, waiting 5 seconds before retry...')
+          sleep 5
+        else
+          raise "OpenSearch failed to become ready after #{max_attempts * 5} seconds. Please check OpenSearch logs."
+        end
+      end
+    end
+
+    Chef::Log.info('OpenSearch readiness verified successfully!')
+  end
+  action :run
+end
 
 execute 'add internal user to opensearch security plugin' do
   command 'export JAVA_HOME="/opt/opscode/embedded/open-jre/"; ./securityadmin.sh   -f ../securityconfig/internal_users.yml   -icl -nhnv -cert /opt/opscode/embedded/opensearch/config/admin.pem   -cacert /opt/opscode/embedded/opensearch/config/root-ca.pem   -key /opt/opscode/embedded/opensearch/config/admin-key.pem'
   cwd '/opt/opscode/embedded/opensearch/plugins/opensearch-security/tools/'
   user OmnibusHelper.new(node).ownership['owner']
-  retries 10
-  retry_delay 1
+  retries 5
+  retry_delay 15
 end
 
 include_recipe 'infra-server::opensearch_index'