diff --git a/History.md b/History.md
index 991d7186ce..28570e64fd 100644
--- a/History.md
+++ b/History.md
@@ -33,6 +33,7 @@
   * Log binding on http:// for TCP bindings to make it clickable
 
 * Bugfixes
+  * Improve shutdown reliability (#2312)
   * Close client http connections made to an ssl server with TLSv1.3 (#2116)
   * Do not set user_config to quiet by default to allow for file config (#2074)
   * Always close SSL connection in Puma::ControlCLI (#2211)
diff --git a/lib/puma/events.rb b/lib/puma/events.rb
index 8c2323f73b..c746c9d1a5 100644
--- a/lib/puma/events.rb
+++ b/lib/puma/events.rb
@@ -65,7 +65,8 @@ def register(hook, obj=nil, &blk)
     # Write +str+ to +@stdout+
     #
     def log(str)
-      @stdout.puts format(str)
+      @stdout.puts format(str) if @stdout.respond_to? :puts
+    rescue Errno::EPIPE
     end
 
     def write(str)
diff --git a/lib/puma/server.rb b/lib/puma/server.rb
index 0ef5aa55dc..2ba99f5243 100644
--- a/lib/puma/server.rb
+++ b/lib/puma/server.rb
@@ -317,7 +317,12 @@ def handle_servers
       rescue Exception => e
         @events.unknown_error e, nil, "Exception handling servers"
       ensure
-        @check.close unless @check.closed? # Ruby 2.2 issue
+        begin
+          @check.close unless @check.closed?
+        rescue Errno::EBADF, RuntimeError
+          # RuntimeError is Ruby 2.2 issue, can't modify frozen IOError
+          # Errno::EBADF is infrequently raised
+        end
         @notify.close
         @notify = nil
         @check = nil
@@ -912,7 +917,7 @@ def notify_safely(message)
       @check, @notify = Puma::Util.pipe unless @notify
       begin
         @notify << message
-      rescue IOError
+      rescue IOError, NoMethodError, Errno::EPIPE
          # The server, in another thread, is shutting down
         Thread.current.purge_interrupt_queue if Thread.current.respond_to? :purge_interrupt_queue
       rescue RuntimeError => e
diff --git a/test/helper.rb b/test/helper.rb
index 472407076d..fa5cd20ca3 100644
--- a/test/helper.rb
+++ b/test/helper.rb
@@ -58,8 +58,11 @@ module TimeoutEveryTestCase
   class TestTookTooLong < Timeout::Error
   end
 
-  def capture_exceptions(*)
-    ::Timeout.timeout(RUBY_ENGINE == 'ruby' ? 60 : 120, TestTookTooLong) { super }
+  def time_it
+    t0 = Minitest.clock_time
+    ::Timeout.timeout(RUBY_ENGINE == 'ruby' ? 60 : 120, TestTookTooLong) { yield }
+  ensure
+    self.time = Minitest.clock_time - t0
   end
 end
 
diff --git a/test/test_integration_cluster.rb b/test/test_integration_cluster.rb
index 524cd4ae6c..f409443c79 100644
--- a/test/test_integration_cluster.rb
+++ b/test/test_integration_cluster.rb
@@ -387,7 +387,7 @@ def bad_exit_pids(pids)
   # used with thread_run to define correct 'refused' errors
   def thread_run_refused(unix: false)
     if unix
-      DARWIN ? [Errno::ENOENT, IOError] : [Errno::ENOENT]
+      [Errno::ENOENT, IOError]
     else
       DARWIN ? [Errno::ECONNREFUSED, Errno::EPIPE, EOFError] :
         [Errno::ECONNREFUSED]