diff --git a/src/watchdog/observers/inotify_c.py b/src/watchdog/observers/inotify_c.py
index d6765e14..74c74a6f 100644
--- a/src/watchdog/observers/inotify_c.py
+++ b/src/watchdog/observers/inotify_c.py
@@ -5,6 +5,7 @@
 import ctypes.util
 import errno
 import os
+import select
 import struct
 import threading
 from ctypes import c_char_p, c_int, c_uint32
@@ -148,6 +149,9 @@ def __init__(self, path: bytes, *, recursive: bool = False, event_mask: int | No
             Inotify._raise_error()
         self._inotify_fd = inotify_fd
         self._lock = threading.Lock()
+        self._closed = False
+        self._waiting_to_read = True
+        self._kill_r, self._kill_w = os.pipe()
 
         # Stores the watch descriptor for a given path.
         self._wd_for_path: dict[bytes, int] = {}
@@ -230,13 +234,19 @@ def remove_watch(self, path: bytes) -> None:
     def close(self) -> None:
         """Closes the inotify instance and removes all associated watches."""
         with self._lock:
-            if self._path in self._wd_for_path:
-                wd = self._wd_for_path[self._path]
-                inotify_rm_watch(self._inotify_fd, wd)
+            if not self._closed:
+                self._closed = True
 
-            # descriptor may be invalid because file was deleted
-            with contextlib.suppress(OSError):
-                os.close(self._inotify_fd)
+                if self._path in self._wd_for_path:
+                    wd = self._wd_for_path[self._path]
+                    inotify_rm_watch(self._inotify_fd, wd)
+
+                if self._waiting_to_read:
+                    # inotify_rm_watch() should write data to _inotify_fd and wake
+                    # the thread, but writing to the kill channel will gaurentee this
+                    os.write(self._kill_w, b'!')
+                else:
+                    self._close_resources()
 
     def read_events(self, *, event_buffer_size: int = DEFAULT_EVENT_BUFFER_SIZE) -> list[InotifyEvent]:
         """Reads events from inotify and yields them."""
@@ -276,6 +286,21 @@ def _recursive_simulate(src_path: bytes) -> list[InotifyEvent]:
         event_buffer = None
         while True:
             try:
+                with self._lock:
+                    if self._closed:
+                        return []
+
+                    self._waiting_to_read = True
+
+                select.select([self._inotify_fd, self._kill_r], [], [])
+
+                with self._lock:
+                    self._waiting_to_read = False
+
+                    if self._closed:
+                        self._close_resources()
+                        return []
+
                 event_buffer = os.read(self._inotify_fd, event_buffer_size)
             except OSError as e:
                 if e.errno == errno.EINTR:
@@ -340,6 +365,11 @@ def _recursive_simulate(src_path: bytes) -> list[InotifyEvent]:
 
         return event_list
 
+    def _close_resources(self):
+        os.close(self._inotify_fd)
+        os.close(self._kill_r)
+        os.close(self._kill_w)
+
     # Non-synchronized methods.
     def _add_dir_watch(self, path: bytes, mask: int, *, recursive: bool) -> None:
         """Adds a watch (optionally recursively) for the given directory path
diff --git a/src/watchdog/utils/bricks.py b/src/watchdog/utils/bricks.py
index 8dd0afa7..cdf9af23 100644
--- a/src/watchdog/utils/bricks.py
+++ b/src/watchdog/utils/bricks.py
@@ -72,14 +72,13 @@ def _init(self, maxsize: int) -> None:
         super()._init(maxsize)
         self._last_item = None
 
-    def _put(self, item: Any) -> None:
+    def put(self, item: Any, block: bool = True, timeout: float | None = None) -> None:
         if self._last_item is None or item != self._last_item:
-            super()._put(item)
-            self._last_item = item
-        else:
-            # `put` increments `unfinished_tasks` even if we did not put
-            # anything into the queue here
-            self.unfinished_tasks -= 1
+            super().put(item, block, timeout)
+
+    def _put(self, item: Any) -> None:
+        super()._put(item)
+        self._last_item = item
 
     def _get(self) -> Any:
         item = super()._get()
diff --git a/tests/isolated/eventlet_observer_stops.py b/tests/isolated/eventlet_observer_stops.py
new file mode 100644
index 00000000..1cf82bdd
--- /dev/null
+++ b/tests/isolated/eventlet_observer_stops.py
@@ -0,0 +1,30 @@
+if __name__ == '__main__':
+    import eventlet
+
+    eventlet.monkey_patch()
+
+    import signal
+    import sys
+    import tempfile
+
+    from watchdog.observers import Observer
+    from watchdog.events import LoggingEventHandler
+
+    with tempfile.TemporaryDirectory() as temp_dir:
+        def run_observer():
+            event_handler = LoggingEventHandler()
+            observer = Observer()
+            observer.schedule(event_handler, temp_dir)
+            observer.start()
+            eventlet.sleep(1)
+            observer.stop()
+
+        def on_alarm(signum, frame):
+            print("Observer.stop() never finished!", file=sys.stderr)
+            sys.exit(1)
+
+        signal.signal(signal.SIGALRM, on_alarm)
+        signal.alarm(4)
+
+        thread = eventlet.spawn(run_observer)
+        thread.wait()
diff --git a/tests/isolated/eventlet_skip_repeat_queue.py b/tests/isolated/eventlet_skip_repeat_queue.py
new file mode 100644
index 00000000..05373934
--- /dev/null
+++ b/tests/isolated/eventlet_skip_repeat_queue.py
@@ -0,0 +1,33 @@
+if __name__ == '__main__':
+    import eventlet
+
+    eventlet.monkey_patch()
+
+    from watchdog.utils.bricks import SkipRepeatsQueue
+
+    q = SkipRepeatsQueue(10)
+    q.put('A')
+    q.put('A')
+    q.put('A')
+    q.put('A')
+    q.put('B')
+    q.put('A')
+
+    value = q.get()
+    assert value == 'A'
+    q.task_done()
+
+    assert q.unfinished_tasks == 2
+
+    value = q.get()
+    assert value == 'B'
+    q.task_done()
+
+    assert q.unfinished_tasks == 1
+
+    value = q.get()
+    assert value == 'A'
+    q.task_done()
+
+    assert q.empty()
+    assert q.unfinished_tasks == 0
diff --git a/tests/markers.py b/tests/markers.py
deleted file mode 100644
index 66291fca..00000000
--- a/tests/markers.py
+++ /dev/null
@@ -1,7 +0,0 @@
-from __future__ import annotations
-
-from platform import python_implementation
-
-import pytest
-
-cpython_only = pytest.mark.skipif(python_implementation() != "CPython", reason="CPython only.")
diff --git a/tests/test_inotify_c.py b/tests/test_inotify_c.py
index 5b34e6c5..8d4b59d4 100644
--- a/tests/test_inotify_c.py
+++ b/tests/test_inotify_c.py
@@ -11,6 +11,7 @@
 import errno
 import logging
 import os
+import select
 import struct
 from typing import TYPE_CHECKING
 from unittest.mock import patch
@@ -56,6 +57,13 @@ def test_late_double_deletion(helper: Helper, p: P, event_queue: TestEventQueue,
         + struct_inotify(wd=3, mask=const.IN_IGNORED)
     )
 
+    select_bkp = select.select
+
+    def fakeselect(read_list, *args, **kwargs):
+        if inotify_fd in read_list:
+            return [inotify_fd], [], []
+        return select_bkp(read_list, *args, **kwargs)
+
     os_read_bkp = os.read
 
     def fakeread(fd, length):
@@ -92,8 +100,9 @@ def inotify_rm_watch(fd, wd):
     mock3 = patch.object(inotify_c, "inotify_init", new=inotify_init)
     mock4 = patch.object(inotify_c, "inotify_add_watch", new=inotify_add_watch)
     mock5 = patch.object(inotify_c, "inotify_rm_watch", new=inotify_rm_watch)
+    mock6 = patch.object(select, "select", new=fakeselect)
 
-    with mock1, mock2, mock3, mock4, mock5:
+    with mock1, mock2, mock3, mock4, mock5, mock6:
         start_watching(path=p(""))
         # Watchdog Events
         for evt_cls in [DirCreatedEvent, DirDeletedEvent] * 2:
diff --git a/tests/test_isolated.py b/tests/test_isolated.py
new file mode 100644
index 00000000..2d3ff972
--- /dev/null
+++ b/tests/test_isolated.py
@@ -0,0 +1,24 @@
+import pytest
+import importlib
+
+from watchdog.utils import platform
+
+from .utils import run_isolated_test
+
+
+# Kqueue isn't supported by Eventlet, so BSD is out
+# Current usage ReadDirectoryChangesW on Windows is blocking, though async may be possible
+@pytest.mark.skipif(not platform.is_linux(), reason="Eventlet only supported in Linux")
+def test_observer_stops_in_eventlet():
+    if not importlib.util.find_spec('eventlet'):
+        pytest.skip("eventlet not installed")
+
+    run_isolated_test('eventlet_observer_stops.py')
+
+
+@pytest.mark.skipif(not platform.is_linux(), reason="Eventlet only supported in Linux")
+def test_eventlet_skip_repeat_queue():
+    if not importlib.util.find_spec('eventlet'):
+        pytest.skip("eventlet not installed")
+
+    run_isolated_test('eventlet_skip_repeat_queue.py')
diff --git a/tests/test_skip_repeats_queue.py b/tests/test_skip_repeats_queue.py
index 27b1dfe4..d6f0f411 100644
--- a/tests/test_skip_repeats_queue.py
+++ b/tests/test_skip_repeats_queue.py
@@ -1,14 +1,10 @@
 from __future__ import annotations
 
-import pytest
-
 from watchdog import events
 from watchdog.utils.bricks import SkipRepeatsQueue
 
-from .markers import cpython_only
-
 
-def basic_actions():
+def test_basic_queue():
     q = SkipRepeatsQueue()
 
     e1 = (2, "fred")
@@ -25,10 +21,6 @@ def basic_actions():
     assert q.empty()
 
 
-def test_basic_queue():
-    basic_actions()
-
-
 def test_allow_nonconsecutive():
     q = SkipRepeatsQueue()
 
@@ -86,10 +78,3 @@ def test_consecutives_allowed_across_empties():
     q.put(e1)  # this repeat is allowed because 'last' added is now gone from queue
     assert e1 == q.get()
     assert q.empty()
-
-
-@cpython_only
-def test_eventlet_monkey_patching():
-    eventlet = pytest.importorskip("eventlet")
-    eventlet.monkey_patch()
-    basic_actions()
diff --git a/tests/utils.py b/tests/utils.py
index 8b82f3a8..d8f05b15 100644
--- a/tests/utils.py
+++ b/tests/utils.py
@@ -2,6 +2,8 @@
 
 import dataclasses
 import os
+import subprocess
+import sys
 from queue import Queue
 from typing import Protocol
 
@@ -97,3 +99,29 @@ def close(self) -> None:
         alive = [emitter.is_alive() for emitter in self.emitters]
         self.emitters = []
         assert alive == [False] * len(alive)
+
+
+def run_isolated_test(path):
+    ISOALTED_TEST_PREFIX = os.path.join('tests', 'isolated')
+    path = os.path.abspath(os.path.join(ISOALTED_TEST_PREFIX, path))
+
+    src_dir = os.path.join(os.path.dirname(os.path.dirname(os.path.abspath(__file__))), 'src')
+    new_env = os.environ.copy()
+    new_env['PYTHONPATH'] = os.pathsep.join(sys.path + [src_dir])
+
+    new_argv = [sys.executable, path]
+
+    p = subprocess.Popen(
+        new_argv,
+        env=new_env,
+    )
+
+    # in case test goes haywire, don't let it run forever
+    timeout = 10
+    try:
+        p.communicate(timeout=timeout)
+    except subprocess.TimeoutExpired:
+        p.kill()
+        assert False, 'timed out'
+
+    assert p.returncode == 0