diff --git a/lib/cypress_on_rails/configuration.rb b/lib/cypress_on_rails/configuration.rb
index a128052..9c112ed 100644
--- a/lib/cypress_on_rails/configuration.rb
+++ b/lib/cypress_on_rails/configuration.rb
@@ -22,6 +22,12 @@ class Configuration
     attr_accessor :server_host
     attr_accessor :server_port
     attr_accessor :transactional_server
+    # HTTP path to check for server readiness (default: '/')
+    # Can be set via CYPRESS_RAILS_READINESS_PATH environment variable
+    attr_accessor :server_readiness_path
+    # Timeout in seconds for individual HTTP readiness checks (default: 5)
+    # Can be set via CYPRESS_RAILS_READINESS_TIMEOUT environment variable
+    attr_accessor :server_readiness_timeout
 
     # Attributes for backwards compatibility
     def cypress_folder
@@ -62,6 +68,8 @@ def reset
       self.server_host = ENV.fetch('CYPRESS_RAILS_HOST', 'localhost')
       self.server_port = ENV.fetch('CYPRESS_RAILS_PORT', nil)
       self.transactional_server = true
+      self.server_readiness_path = ENV.fetch('CYPRESS_RAILS_READINESS_PATH', '/')
+      self.server_readiness_timeout = ENV.fetch('CYPRESS_RAILS_READINESS_TIMEOUT', '5').to_i
     end
 
     def tagged_logged
diff --git a/lib/cypress_on_rails/server.rb b/lib/cypress_on_rails/server.rb
index 00168ef..15390f0 100644
--- a/lib/cypress_on_rails/server.rb
+++ b/lib/cypress_on_rails/server.rb
@@ -1,6 +1,7 @@
 require 'socket'
 require 'timeout'
 require 'fileutils'
+require 'net/http'
 require 'cypress_on_rails/configuration'
 
 module CypressOnRails
@@ -9,13 +10,16 @@ class Server
 
     def initialize(options = {})
       config = CypressOnRails.configuration
-      
+
       @framework = options[:framework] || :cypress
       @host = options[:host] || config.server_host
       @port = options[:port] || config.server_port || find_available_port
       @port = @port.to_i if @port
       @install_folder = options[:install_folder] || config.install_folder || detect_install_folder
       @transactional = options.fetch(:transactional, config.transactional_server)
+      # Process management: track PID and process group for proper cleanup
+      @server_pid = nil
+      @server_pgid = nil
     end
 
     def open
@@ -105,34 +109,91 @@ def spawn_server
 
       puts "Starting Rails server: #{server_args.join(' ')}"
 
-      spawn(*server_args, out: $stdout, err: $stderr)
+      @server_pid = spawn(*server_args, out: $stdout, err: $stderr, pgroup: true)
+      begin
+        @server_pgid = Process.getpgid(@server_pid)
+      rescue Errno::ESRCH => e
+        # Edge case: process terminated before we could get pgid
+        # This is OK - send_term_signal will fall back to single-process kill
+        CypressOnRails.configuration.logger.warn("Process #{@server_pid} terminated immediately after spawn: #{e.message}")
+        @server_pgid = nil
+      end
+      @server_pid
     end
 
     def wait_for_server(timeout = 30)
       Timeout.timeout(timeout) do
         loop do
-          begin
-            TCPSocket.new(host, port).close
-            break
-          rescue Errno::ECONNREFUSED, Errno::EHOSTUNREACH
-            sleep 0.1
-          end
+          break if server_responding?
+          sleep 0.1
         end
       end
     rescue Timeout::Error
       raise "Rails server failed to start on #{host}:#{port} after #{timeout} seconds"
     end
 
+    def server_responding?
+      config = CypressOnRails.configuration
+      readiness_path = config.server_readiness_path || '/'
+      timeout = config.server_readiness_timeout || 5
+      uri = URI("http://#{host}:#{port}#{readiness_path}")
+
+      response = Net::HTTP.start(uri.host, uri.port, open_timeout: timeout, read_timeout: timeout) do |http|
+        http.get(uri.path)
+      end
+
+      # Accept 200-399 (success and redirects), reject 404 and 5xx
+      # 3xx redirects are considered "ready" because the server is responding correctly
+      (200..399).cover?(response.code.to_i)
+    rescue Errno::ECONNREFUSED, Errno::EADDRNOTAVAIL, Errno::ETIMEDOUT, SocketError,
+           Net::OpenTimeout, Net::ReadTimeout, Net::HTTPBadResponse
+      false
+    end
+
     def stop_server(pid)
-      if pid
-        puts "Stopping Rails server (PID: #{pid})"
-        Process.kill('TERM', pid)
-        Process.wait(pid)
+      return unless pid
+
+      puts "Stopping Rails server (PID: #{pid})"
+      send_term_signal(pid)
+
+      begin
+        Timeout.timeout(10) do
+          Process.wait(pid)
+        end
+      rescue Timeout::Error
+        CypressOnRails.configuration.logger.warn("Server did not terminate after TERM signal, sending KILL")
+        safe_kill_process('KILL', pid)
+        Process.wait(pid) rescue Errno::ESRCH
       end
     rescue Errno::ESRCH
       # Process already terminated
     end
 
+    def send_term_signal(pid)
+      if @server_pgid && process_exists?(pid)
+        Process.kill('TERM', -@server_pgid)
+      else
+        safe_kill_process('TERM', pid)
+      end
+    rescue Errno::ESRCH, Errno::EPERM => e
+      CypressOnRails.configuration.logger.warn("Failed to kill process group #{@server_pgid}: #{e.message}, trying single process")
+      safe_kill_process('TERM', pid)
+    end
+
+    def process_exists?(pid)
+      return false unless pid
+      Process.kill(0, pid)
+      true
+    rescue Errno::ESRCH, Errno::EPERM
+      false
+    end
+
+    def safe_kill_process(signal, pid)
+      Process.kill(signal, pid) if pid
+    rescue Errno::ESRCH, Errno::EPERM
+      # Process already terminated or permission denied
+    end
+
     def base_url
       "http://#{host}:#{port}"
     end
diff --git a/spec/cypress_on_rails/configuration_spec.rb b/spec/cypress_on_rails/configuration_spec.rb
index f790abf..3652e8d 100644
--- a/spec/cypress_on_rails/configuration_spec.rb
+++ b/spec/cypress_on_rails/configuration_spec.rb
@@ -10,6 +10,8 @@
     expect(CypressOnRails.configuration.logger).to_not be_nil
     expect(CypressOnRails.configuration.before_request).to_not be_nil
     expect(CypressOnRails.configuration.vcr_options).to eq({})
+    expect(CypressOnRails.configuration.server_readiness_path).to eq('/')
+    expect(CypressOnRails.configuration.server_readiness_timeout).to eq(5)
   end
 
   it 'can be configured' do
@@ -22,6 +24,8 @@
       config.logger = my_logger
       config.before_request = before_request_lambda
       config.vcr_options = { hook_into: :webmock }
+      config.server_readiness_path = '/health'
+      config.server_readiness_timeout = 10
     end
     expect(CypressOnRails.configuration.api_prefix).to eq('/api')
     expect(CypressOnRails.configuration.install_folder).to eq('my/path')
@@ -29,5 +33,7 @@
     expect(CypressOnRails.configuration.logger).to eq(my_logger)
     expect(CypressOnRails.configuration.before_request).to eq(before_request_lambda)
     expect(CypressOnRails.configuration.vcr_options).to eq(hook_into: :webmock)
+    expect(CypressOnRails.configuration.server_readiness_path).to eq('/health')
+    expect(CypressOnRails.configuration.server_readiness_timeout).to eq(10)
   end
 end