diff --git a/sdks/python/apache_beam/runners/portability/portable_runner.py b/sdks/python/apache_beam/runners/portability/portable_runner.py
index 94a467d5a249..e081185b5507 100644
--- a/sdks/python/apache_beam/runners/portability/portable_runner.py
+++ b/sdks/python/apache_beam/runners/portability/portable_runner.py
@@ -218,14 +218,12 @@ def run(
     """Run the job"""
     try:
       state_stream = self.job_service.GetStateStream(
-          beam_job_api_pb2.GetJobStateRequest(job_id=preparation_id),
-          timeout=self.timeout)
+          beam_job_api_pb2.GetJobStateRequest(job_id=preparation_id))
       # If there's an error, we don't always get it until we try to read.
       # Fortunately, there's always an immediate current state published.
       state_stream = itertools.chain([next(state_stream)], state_stream)
       message_stream = self.job_service.GetMessageStream(
-          beam_job_api_pb2.JobMessagesRequest(job_id=preparation_id),
-          timeout=self.timeout)
+          beam_job_api_pb2.JobMessagesRequest(job_id=preparation_id))
     except Exception:
       # TODO(https://github.com/apache/beam/issues/19284): Unify preparation_id
       # and job_id for all runners.
diff --git a/sdks/python/apache_beam/utils/multi_process_shared.py b/sdks/python/apache_beam/utils/multi_process_shared.py
index de4b94bc5da3..0c672910f257 100644
--- a/sdks/python/apache_beam/utils/multi_process_shared.py
+++ b/sdks/python/apache_beam/utils/multi_process_shared.py
@@ -26,6 +26,7 @@
 import logging
 import multiprocessing.managers
 import os
+import socket
 import tempfile
 import threading
 import time
@@ -85,6 +86,7 @@ def singletonProxy_release(self):
   def singletonProxy_unsafe_hard_delete(self):
     assert self._SingletonProxy_valid
     self._SingletonProxy_entry.unsafe_hard_delete()
+    self._SingletonProxy_valid = False
 
   def __getattr__(self, name):
     if not self._SingletonProxy_valid:
@@ -231,6 +233,26 @@ def unsafe_hard_delete(self):
     self._proxyObject.unsafe_hard_delete()
 
 
+def _wait_for_server_readiness(address, timeout=60):
+  start = time.time()
+  wait_secs = 0.1
+
+  while time.time() - start < timeout:
+    try:
+      s = socket.create_connection(address, timeout=wait_secs)
+      s.close()
+      return
+    except OSError:
+      wait_secs *= 1.2
+      logging.log(
+          logging.WARNING if wait_secs > 1 else logging.DEBUG,
+          'Waiting for server to be ready at %s',
+          address)
+
+  raise RuntimeError(
+      f"Server at {address} failed to accept connections within {timeout}s")
+
+
 def _run_server_process(address_file, tag, constructor, authkey, life_line):
   """
     Runs in a separate process.
@@ -292,9 +314,14 @@ def _monitor_parent():
     logging.info(
         'Process %s: Proxy serving %s at %s', os.getpid(), tag, server.address)
 
-    with open(address_file + '.tmp', 'w') as fout:
-      fout.write('%s:%d' % server.address)
-    os.rename(address_file + '.tmp', address_file)
+    def publish_address():
+      _wait_for_server_readiness(server.address)
+      with open(address_file + '.tmp', 'w') as fout:
+        fout.write('%s:%d' % server.address)
+      os.rename(address_file + '.tmp', address_file)
+
+    t_pub = threading.Thread(target=publish_address)
+    t_pub.start()
 
     server.serve_forever()
 
@@ -392,12 +419,30 @@ def _get_manager(self):
               manager = _SingletonRegistrar(
                   address=(host, int(port)), authkey=AUTH_KEY)
               multiprocessing.current_process().authkey = AUTH_KEY
-              try:
-                manager.connect()
-                self._manager = manager
-              except ConnectionError:
-                # The server is no longer good, assume it died.
-                os.unlink(address_file)
+              last_error = None
+              for attempt in range(
+                  3):  # Retry transient connection failures (e.g. CI)
+                try:
+                  manager.connect()
+                  self._manager = manager
+                  last_error = None
+                  break
+                except (ConnectionError, OSError) as e:
+                  last_error = e
+                  if attempt < 2:
+                    time.sleep(0.2 * (attempt + 1))
+              if self._manager is None and last_error is not None:
+                # Only unlink and retry from scratch if we use a separate server
+                # process; in-process server state would be stale and re-entry
+                # would raise.
+                if self._spawn_process:
+                  logging.warning(
+                      'Connection to proxy at %s failed after retries: %s',
+                      address,
+                      last_error)
+                  os.unlink(address_file)
+                else:
+                  raise last_error
 
     return self._manager
 
@@ -497,7 +542,12 @@ def cleanup_process():
               "Shared Server Process died unexpectedly"
               f" with exit code {exit_code}")
 
-        if time.time() - last_log > 300:
+        if time.time() - start_time > 60:
+          if p.is_alive(): p.terminate()
+          raise RuntimeError(
+              "Shared Server Process failed to initialize within 60 seconds")
+
+        if time.time() - last_log > 5:
           logging.warning(
               "Still waiting for %s to initialize... %ss elapsed)",
               self._tag,
@@ -522,9 +572,12 @@ def cleanup_process():
           'Starting proxy server at %s for shared %s',
           self._server.address,
           self._tag)
+      t = threading.Thread(target=self._server.serve_forever, daemon=True)
+      t.start()
+
+      _wait_for_server_readiness(self._server.address)
+
       with open(address_file + '.tmp', 'w') as fout:
         fout.write('%s:%d' % self._server.address)
       os.rename(address_file + '.tmp', address_file)
-      t = threading.Thread(target=self._server.serve_forever, daemon=True)
-      t.start()
       logging.info('Done starting server')
diff --git a/sdks/python/apache_beam/utils/multi_process_shared_test.py b/sdks/python/apache_beam/utils/multi_process_shared_test.py
index 7b2b11857bfd..2c7758564f4e 100644
--- a/sdks/python/apache_beam/utils/multi_process_shared_test.py
+++ b/sdks/python/apache_beam/utils/multi_process_shared_test.py
@@ -19,10 +19,12 @@
 import logging
 import multiprocessing
 import os
+import shutil
 import tempfile
 import threading
 import unittest
 from typing import Any
+from unittest import mock
 
 from apache_beam.utils import multi_process_shared
 
@@ -460,6 +462,118 @@ def test_zombie_reaping_on_acquire(self):
       pass
 
 
+class WaitForServerReadinessTest(unittest.TestCase):
+  def test_wait_for_server_readiness_timeout_raises(self):
+    with mock.patch.object(multi_process_shared.socket,
+                           'create_connection',
+                           side_effect=OSError('connection refused')):
+      with self.assertRaises(RuntimeError) as ctx:
+        multi_process_shared._wait_for_server_readiness(('localhost', 12345),
+                                                        timeout=0.2)
+      self.assertIn('failed to accept connections', str(ctx.exception))
+
+  def test_wait_for_server_readiness_success(self):
+    mock_socket = mock.Mock()
+    with mock.patch.object(multi_process_shared.socket,
+                           'create_connection',
+                           return_value=mock_socket):
+      multi_process_shared._wait_for_server_readiness(('localhost', 12345),
+                                                      timeout=1.0)
+    mock_socket.close.assert_called_once()
+
+  def test_wait_for_server_readiness_retries_on_oserror_then_succeeds(self):
+    mock_socket = mock.Mock()
+    with mock.patch.object(multi_process_shared.socket,
+                           'create_connection',
+                           side_effect=[OSError('refused'),
+                                        OSError('refused'),
+                                        mock_socket]):
+      multi_process_shared._wait_for_server_readiness(('localhost', 12345),
+                                                      timeout=2.0)
+    mock_socket.close.assert_called_once()
+
+
+class AutoProxyWrapperUnsafeHardDeleteTest(unittest.TestCase):
+  def test_wrapper_unsafe_hard_delete(self):
+    shared = multi_process_shared.MultiProcessShared(
+        Counter, tag='test_wrapper_unsafe_hard_delete', always_proxy=True)
+    obj = shared.acquire()
+    self.assertEqual(obj.get(), 0)
+    obj.increment()
+    try:
+      obj.unsafe_hard_delete()
+    except Exception:
+      pass
+    with self.assertRaises(Exception):
+      obj.get()
+
+
+class GetManagerRetryTest(unittest.TestCase):
+  def setUp(self):
+    self.tempdir = tempfile.mkdtemp()
+    self.addCleanup(shutil.rmtree, self.tempdir, ignore_errors=True)
+
+  def test_get_manager_retries_on_connection_error_then_succeeds(self):
+    address_file = os.path.join(self.tempdir, 'tag_retry') + '.address'
+    with open(address_file, 'w') as f:
+      f.write('127.0.0.1:0')
+    shared = multi_process_shared.MultiProcessShared(
+        Counter, tag='tag_retry', path=self.tempdir, always_proxy=True)
+    with mock.patch.object(multi_process_shared._SingletonRegistrar,
+                           'connect',
+                           side_effect=[ConnectionError('refused'), None]):
+      manager = shared._get_manager()
+    self.assertIsNotNone(manager)
+
+  def test_get_manager_raises_when_connection_fails_no_spawn(self):
+    address_file = os.path.join(self.tempdir, 'tag_fail') + '.address'
+    with open(address_file, 'w') as f:
+      f.write('127.0.0.1:99999')
+    shared = multi_process_shared.MultiProcessShared(
+        Counter,
+        tag='tag_fail',
+        path=self.tempdir,
+        always_proxy=True,
+        spawn_process=False)
+
+    with mock.patch.object(multi_process_shared._SingletonRegistrar,
+                           'connect',
+                           side_effect=ConnectionError('refused')):
+      with self.assertRaises((ConnectionError, OSError)):
+        shared._get_manager()
+
+  def test_get_manager_unlinks_when_spawn_connection_fails(self):
+    address_file = os.path.join(self.tempdir, 'tag_spawn_fail') + '.address'
+    with open(address_file, 'w') as f:
+      f.write('127.0.0.1:99999')
+    shared = multi_process_shared.MultiProcessShared(
+        Counter,
+        tag='tag_spawn_fail',
+        path=self.tempdir,
+        always_proxy=False,
+        spawn_process=True)
+    unlink_calls = []
+
+    def track_unlink(path):
+      unlink_calls.append(path)
+      os.unlink(path)
+
+    def mock_create_server(_):
+      multi_process_shared._process_level_singleton_manager.register_singleton(
+          Counter, shared._tag)
+      shared._manager = multi_process_shared._process_level_singleton_manager
+
+    with mock.patch.object(multi_process_shared._SingletonRegistrar,
+                           'connect',
+                           side_effect=ConnectionError('refused')):
+      with mock.patch.object(multi_process_shared.os,
+                             'unlink',
+                             side_effect=track_unlink):
+        with mock.patch.object(shared, '_create_server', mock_create_server):
+          shared._get_manager()
+    self.assertGreater(len(unlink_calls), 0)
+
+
 if __name__ == '__main__':
   logging.getLogger().setLevel(logging.INFO)
   unittest.main()
diff --git a/sdks/python/apache_beam/yaml/yaml_transform_unit_test.py b/sdks/python/apache_beam/yaml/yaml_transform_unit_test.py
index f83697732598..843db0170b23 100644
--- a/sdks/python/apache_beam/yaml/yaml_transform_unit_test.py
+++ b/sdks/python/apache_beam/yaml/yaml_transform_unit_test.py
@@ -55,6 +55,13 @@ def new_pipeline():
           pickle_library='cloudpickle'))
 
 
+def new_pipeline_expand_test():
+  return beam.Pipeline(
+      runner='FnApiRunner',
+      options=beam.options.pipeline_options.PipelineOptions(
+          pickle_library='cloudpickle'))
+
+
 @unittest.skipIf(jsonschema is None, "Yaml dependencies not installed")
 class MainTest(unittest.TestCase):
   def assertYaml(self, expected, result):
@@ -1048,7 +1055,7 @@ def test_expand_pipeline_with_pipeline_key_only(self):
               elements: [1,2,3]
           - type: LogForTesting
     '''
-    with new_pipeline() as p:
+    with new_pipeline_expand_test() as p:
       expand_pipeline(p, spec, validate_schema=None)
 
   def test_expand_pipeline_with_pipeline_and_option_keys(self):
@@ -1063,7 +1070,7 @@ def test_expand_pipeline_with_pipeline_and_option_keys(self):
       options:
         streaming: false
     '''
-    with new_pipeline() as p:
+    with new_pipeline_expand_test() as p:
       expand_pipeline(p, spec, validate_schema=None)
 
   def test_expand_pipeline_with_extra_top_level_keys(self):
@@ -1082,7 +1089,7 @@ def test_expand_pipeline_with_extra_top_level_keys(self):
 
       other_metadata: "This is an ignored comment."
     '''
-    with new_pipeline() as p:
+    with new_pipeline_expand_test() as p:
       expand_pipeline(p, spec, validate_schema=None)
 
   def test_expand_pipeline_with_incorrect_pipelines_key_fails(self):
@@ -1095,7 +1102,7 @@ def test_expand_pipeline_with_incorrect_pipelines_key_fails(self):
               elements: [1,2,3]
           - type: LogForTesting
     '''
-    with new_pipeline() as p:
+    with new_pipeline_expand_test() as p:
       with self.assertRaises(KeyError):
         expand_pipeline(p, spec, validate_schema=None)
 
@@ -1110,7 +1117,7 @@ def test_expand_pipeline_with_valid_schema(self):
               elements: [1,2,3]
           - type: LogForTesting
     '''
-    with new_pipeline() as p:
+    with new_pipeline_expand_test() as p:
       expand_pipeline(p, spec, validate_schema='generic')
 
   @unittest.skipIf(jsonschema is None, "Yaml dependencies not installed")
@@ -1124,7 +1131,7 @@ def test_expand_pipeline_with_invalid_schema(self):
               elements: [1,2,3]
           - type: LogForTesting
     '''
-    with new_pipeline() as p:
+    with new_pipeline_expand_test() as p:
       with self.assertRaises(jsonschema.ValidationError):
         expand_pipeline(p, spec, validate_schema='generic')
 
diff --git a/sdks/python/scripts/run_tox_cleanup.sh b/sdks/python/scripts/run_tox_cleanup.sh
index be4409525b53..89f5a6c61810 100755
--- a/sdks/python/scripts/run_tox_cleanup.sh
+++ b/sdks/python/scripts/run_tox_cleanup.sh
@@ -35,7 +35,7 @@ set -e
 for dir in apache_beam target/build; do
     if [ -d "${dir}" ]; then
         for ext in pyc c so; do
-            find ${dir} -type f -name "*.${ext}" -delete
+            find ${dir} -type f -name "*.${ext}" -delete || true
         done
     fi
 done