diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index f3f4b09a..10098503 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -65,7 +65,7 @@ On Linux or macOS:
 ```
 .../debugpy$ python3 -m tox
 ```
-This will perform a full run with the default settings. A full run will run tests on Python 2.7 and 3.5-3.8, and requires all of those to be installed. If some versions are missing, or it is desired to skip them for a particular run, tox can be directed to only run tests on specific versions with `-e`. In addition, the `--developer` option can be used to skip the packaging step, running tests directly against the source code in `src/debugpy`. This should only be used when iterating on the code, and a proper run should be performed before submitting a PR. On Windows:
+This will perform a full run with the default settings. A full run will run tests on Python 2.7 and 3.5-3.8, and requires all of those to be installed. If some versions are missing, or it is desired to skip them for a particular run, tox can be directed to only run tests on specific versions with `-e`. In addition, the `--develop` option can be used to skip the packaging step, running tests directly against the source code in `src/debugpy`. This should only be used when iterating on the code, and a proper run should be performed before submitting a PR. On Windows:
 ```
 ...\debugpy> py -m tox -e py27,py37 --develop
 ```
diff --git a/pyproject.toml b/pyproject.toml
index 3addae67..b2011ad7 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -22,6 +22,7 @@ executionEnvironments = [
   { root = "src" }, { root = "." }
 ]
 typeCheckingMode = "standard"
+enableTypeIgnoreComments = false
 
 [tool.ruff]
 # Enable the pycodestyle (`E`) and Pyflakes (`F`) rules by default.
diff --git a/src/debugpy/adapter/servers.py b/src/debugpy/adapter/servers.py
index 219a85a6..b581d4e3 100644
--- a/src/debugpy/adapter/servers.py
+++ b/src/debugpy/adapter/servers.py
@@ -19,8 +19,6 @@ from debugpy.adapter import components, sessions
 import traceback
 import io
 
-from debugpy.common.util import WaitForTimeout
-
 access_token = None
 """Access token used to authenticate with the servers."""
 
@@ -431,11 +429,14 @@ def wait_for_connection(session, predicate, timeout: Union[float, None]=None):
     If there is more than one server connection already available, returns the oldest
     one.
     """
-    def after_wait():
+    def wait_for_timeout():
+        if timeout is not None:
+            time.sleep(timeout)
+        wait_for_timeout.timed_out = True # pyright: ignore[reportFunctionMemberAccess]
         with _lock:
             _connections_changed.set()
-    wait_for_timeout = WaitForTimeout(timeout, after_wait)
 
+    wait_for_timeout.timed_out = timeout == 0 # pyright: ignore[reportFunctionMemberAccess]
     if timeout:
         thread = threading.Thread(
             target=wait_for_timeout, name="servers.wait_for_connection() timeout"
@@ -450,7 +451,7 @@ def wait_for_connection(session, predicate, timeout: Union[float, None]=None):
             _connections_changed.clear()
             conns = (conn for conn in _connections if predicate(conn))
             conn = next(conns, None)
-            if conn is not None or wait_for_timeout.timed_out:
+            if conn is not None or wait_for_timeout.timed_out: # pyright: ignore[reportFunctionMemberAccess]
                 return conn
         _connections_changed.wait()
 
diff --git a/src/debugpy/adapter/sessions.py b/src/debugpy/adapter/sessions.py
index 7b17b93a..5b3ea748 100644
--- a/src/debugpy/adapter/sessions.py
+++ b/src/debugpy/adapter/sessions.py
@@ -6,6 +6,7 @@ import itertools
 import os
 import signal
 import threading
+import time
 from typing import Union
 
 from debugpy import common
@@ -112,8 +113,14 @@ class Session(util.Observable):
         seconds regardless of whether the predicate was satisfied. The method returns
         False if it timed out, and True otherwise.
         """
-        wait_for_timeout = util.WaitForTimeout(timeout, lambda: self.notify_changed())
+        def wait_for_timeout():
+            if timeout is not None:
+                time.sleep(timeout)
+            wait_for_timeout.timed_out = True # pyright: ignore[reportFunctionMemberAccess]
+            self.notify_changed()
 
+        wait_for_timeout.timed_out = False # pyright: ignore[reportFunctionMemberAccess]
+        
         if timeout is not None:
             thread = threading.Thread(
                 target=wait_for_timeout, name="Session.wait_for() timeout"
@@ -123,7 +130,7 @@ class Session(util.Observable):
 
         with self:
             while not predicate():
-                if wait_for_timeout.timed_out:
+                if wait_for_timeout.timed_out: # pyright: ignore[reportFunctionMemberAccess]
                     return False
                 self._changed_condition.wait()
             return True
diff --git a/src/debugpy/common/log.py b/src/debugpy/common/log.py
index 343cf50f..d52c9295 100644
--- a/src/debugpy/common/log.py
+++ b/src/debugpy/common/log.py
@@ -12,8 +12,12 @@ import platform
 import sys
 import threading
 import traceback
-from typing import Any, NoReturn, Protocol, Union
-from typing_extensions import TypeIs
+from typing import TYPE_CHECKING, Any, NoReturn, Protocol, Union
+
+if TYPE_CHECKING:
+    # Careful not force this import in production code, as it's not available in all
+    # code that we run.
+    from typing_extensions import TypeIs
 
 import debugpy
 from debugpy.common import json, timestamp, util
@@ -283,7 +287,7 @@ def prefixed(format_string, *args, **kwargs):
 class HasName(Protocol):
     name: str
 
-def has_name(obj: Any) -> TypeIs[HasName]:
+def has_name(obj: Any) -> "TypeIs[HasName]":
     try:
         return hasattr(obj, "name")
     except NameError:
diff --git a/src/debugpy/common/messaging.py b/src/debugpy/common/messaging.py
index 39e46ddf..a0428232 100644
--- a/src/debugpy/common/messaging.py
+++ b/src/debugpy/common/messaging.py
@@ -20,8 +20,11 @@ import os
 import socket
 import sys
 import threading
-from typing import BinaryIO, Callable, Union, cast, Any
-from typing_extensions import TypeIs
+from typing import TYPE_CHECKING, BinaryIO, Callable, Union, cast, Any
+if TYPE_CHECKING:
+    # Careful not force this import in production code, as it's not available in all
+    # code that we run.
+    from typing_extensions import TypeIs
 
 from debugpy.common import json, log, util
 from debugpy.common.util import hide_thread_from_debugger
@@ -429,7 +432,7 @@ class AssociableMessageDict(MessageDict):
     def associate_with(self, message: Message):
         self.message = message
 
-def is_associable(obj) -> TypeIs[AssociableMessageDict]:
+def is_associable(obj) -> "TypeIs[AssociableMessageDict]":
     return isinstance(obj, MessageDict) and hasattr(obj, "associate_with")
 
 def _payload(value):
diff --git a/src/debugpy/common/util.py b/src/debugpy/common/util.py
index b87d7640..bc519320 100644
--- a/src/debugpy/common/util.py
+++ b/src/debugpy/common/util.py
@@ -165,14 +165,3 @@ def hide_thread_from_debugger(thread):
         thread.pydev_do_not_trace = True
         thread.is_pydev_daemon_thread = True
 
-class WaitForTimeout():
-    def __init__(self, timeout: Union[float, None], func: Callable[[], None]):
-        self._func = func
-        self._timeout = timeout
-        self.timed_out = False
-
-    def __call__(self):
-        if self._timeout is not None:
-            time.sleep(self._timeout)
-            self.timed_out = True
-        self._func()
diff --git a/tests/logs.py b/tests/logs.py
index 7d3089ca..3b7f6d74 100644
--- a/tests/logs.py
+++ b/tests/logs.py
@@ -4,12 +4,27 @@
 
 import io
 import os
+import shutil
 import pytest_timeout
 import sys
 
 from debugpy.common import json, log
 
 
+def write_title(title, stream=None, sep="~"):
+    """Write a section title.
+    If *stream* is None sys.stderr will be used, *sep* is used to
+    draw the line.
+    """
+    if stream is None:
+        stream = sys.stderr
+    width, height = shutil.get_terminal_size()
+    fill = int((width - len(title) - 2) / 2)
+    line = " ".join([sep * fill, title, sep * fill])
+    if len(line) < width:
+        line += sep * (width - len(line))
+    stream.write("\n" + line + "\n")
+
 def dump():
     if log.log_dir is None:
         return
@@ -27,5 +42,5 @@ def dump():
                 pass
             else:
                 path = os.path.relpath(path, log.log_dir)
-                pytest_timeout.write_title(path)
+                write_title(path)
                 print(s, file=sys.stderr)
diff --git a/tests/pytest_hooks.py b/tests/pytest_hooks.py
index f37eecb8..7ef3851f 100644
--- a/tests/pytest_hooks.py
+++ b/tests/pytest_hooks.py
@@ -7,7 +7,7 @@ import pytest
 import pytest_timeout
 import sys
 
-from debugpy.common import log
+from debugpy.common import log # pyright: ignore[reportAttributeAccessIssue]
 import tests
 from tests import logs
 
@@ -56,9 +56,8 @@ def pytest_runtest_makereport(item, call):
 def pytest_make_parametrize_id(config, val):
     return getattr(val, "pytest_id", None)
 
-
 # If a test times out and pytest tries to print the stacks of where it was hanging,
 # we want to print the pydevd log as well. This is not a normal pytest hook - we
 # just detour pytest_timeout.dump_stacks directly.
 _dump_stacks = pytest_timeout.dump_stacks
-pytest_timeout.dump_stacks = lambda: (_dump_stacks(), logs.dump())
+pytest_timeout.dump_stacks = lambda terminal: (_dump_stacks(terminal), logs.dump())
diff --git a/tests/requirements.txt b/tests/requirements.txt
index 5b8a498c..7d48234e 100644
--- a/tests/requirements.txt
+++ b/tests/requirements.txt
@@ -19,3 +19,4 @@ flask
 gevent
 numpy
 requests
+typing_extensions
\ No newline at end of file