diff --git a/src/debugpy/adapter/clients.py b/src/debugpy/adapter/clients.py
index 03a14db8..84084dd1 100644
--- a/src/debugpy/adapter/clients.py
+++ b/src/debugpy/adapter/clients.py
@@ -219,9 +219,9 @@ class Client(components.Component):
             if self.session.no_debug:
                 servers.dont_wait_for_first_connection()
 
-            request("debugOptions", json.array(str))
+            request_options = request("debugOptions", json.array(str))
             self.session.debug_options = debug_options = set(
-                
+                request_options
             )
 
             f(self, request)
@@ -656,7 +656,7 @@ class Client(components.Component):
         result = {"debugpy": {"version": debugpy.__version__}}
         if self.server:
             try:
-                pydevd_info: messaging.AssociatableMessageDict = self.server.channel.request("pydevdSystemInfo")
+                pydevd_info: messaging.MessageDict = self.server.channel.request("pydevdSystemInfo")
             except Exception:
                 # If the server has already disconnected, or couldn't handle it,
                 # report what we've got.
@@ -777,7 +777,7 @@ class Client(components.Component):
 
 def serve(host, port):
     global listener
-    listener = sockets.serve("Client", Client, host, port) # type: ignore
+    listener = sockets.serve("Client", Client, host, port)
     sessions.report_sockets()
     return listener.getsockname()
 
diff --git a/src/debugpy/adapter/servers.py b/src/debugpy/adapter/servers.py
index 77575f01..219a85a6 100644
--- a/src/debugpy/adapter/servers.py
+++ b/src/debugpy/adapter/servers.py
@@ -399,7 +399,7 @@ class Server(components.Component):
 
 def serve(host="127.0.0.1", port=0):
     global listener
-    listener = sockets.serve("Server", Connection, host, port) # type: ignore
+    listener = sockets.serve("Server", Connection, host, port)
     sessions.report_sockets()
     return listener.getsockname()
 
diff --git a/src/debugpy/common/messaging.py b/src/debugpy/common/messaging.py
index fa9bfe7b..39e46ddf 100644
--- a/src/debugpy/common/messaging.py
+++ b/src/debugpy/common/messaging.py
@@ -408,7 +408,7 @@ class MessageDict(collections.OrderedDict):
             raise message.isnt_valid("{0}{1}", json.repr(key), err)
         return value
 
-    def _invalid_if_no_key(func: Callable[..., Any]): # type: ignore
+    def _invalid_if_no_key(func: Callable[..., Any]): # pyright: ignore[reportSelfClsParameterName]
         def wrap(self, key, *args, **kwargs):
             try:
                 return func(self, key, *args, **kwargs)
@@ -425,11 +425,11 @@ class MessageDict(collections.OrderedDict):
     del _invalid_if_no_key
 
 
-class AssociatableMessageDict(MessageDict):
+class AssociableMessageDict(MessageDict):
     def associate_with(self, message: Message):
         self.message = message
 
-def is_associatable(obj) -> TypeIs[AssociatableMessageDict]:
+def is_associable(obj) -> TypeIs[AssociableMessageDict]:
     return isinstance(obj, MessageDict) and hasattr(obj, "associate_with")
 
 def _payload(value):
@@ -446,7 +446,7 @@ def _payload(value):
     # Missing payload. Construct a dummy MessageDict, and make it look like it was
     # deserialized. See JsonMessageChannel._parse_incoming_message for why it needs
     # to have associate_with().
-    value = AssociatableMessageDict(None)
+    value = AssociableMessageDict(None)
     return value
 
 
@@ -471,7 +471,7 @@ class Message(object):
         """
 
     def __str__(self):
-        return json.repr(self.json).__str__() if self.json is not None else repr(self)
+        return str(json.repr(self.json)) if self.json is not None else repr(self)
 
     def describe(self):
         """A brief description of the message that is enough to identify it.
@@ -483,14 +483,17 @@ class Message(object):
         raise NotImplementedError
 
     @property
-    def payload(self) -> MessageDict:
+    def payload(self) -> MessageDict | Exception:
         """Payload of the message - self.body or self.arguments, depending on the
         message type.
         """
         raise NotImplementedError
 
-    def __call__(self, *args, **kwargs):
+    def __call__(self, *args, **kwargs) -> MessageDict | Any | int | float:
         """Same as self.payload(...)."""
+        assert not isinstance(self.payload, Exception)
+        if args.count == 0 and kwargs == {}:
+            return self.payload
         return self.payload(*args, **kwargs)
 
     def __contains__(self, key):
@@ -573,12 +576,12 @@ class Event(Message):
     the appropriate exception type that applies_to() the Event object.
     """
 
-    def __init__(self, channel, seq, event, body, json=None):
+    def __init__(self, channel, seq, event, body: MessageDict, json=None):
         super().__init__(channel, seq, json)
 
         self.event = event
 
-        if is_associatable(body):
+        if is_associable(body):
             body.associate_with(self)
         self.body = body
 
@@ -667,12 +670,12 @@ class Request(Message):
     the appropriate exception type that applies_to() the Request object.
     """
 
-    def __init__(self, channel, seq, command, arguments, json=None):
+    def __init__(self, channel, seq, command, arguments: MessageDict, json=None):
         super().__init__(channel, seq, json)
 
         self.command = command
 
-        if is_associatable(arguments):
+        if is_associable(arguments):
             arguments.associate_with(self)
         self.arguments = arguments
 
@@ -787,7 +790,7 @@ class OutgoingRequest(Request):
     def describe(self):
         return f"{self.seq} request {json.repr(self.command)} to {self.channel}"
 
-    def wait_for_response(self, raise_if_failed=True)-> AssociatableMessageDict | Exception:
+    def wait_for_response(self, raise_if_failed=True)-> MessageDict:
         """Waits until a response is received for this request, records the Response
         object for it in self.response, and returns response.body.
 
@@ -804,6 +807,8 @@ class OutgoingRequest(Request):
 
         if raise_if_failed and not self.response.success and isinstance( self.response.body, BaseException):
             raise self.response.body
+        
+        assert not isinstance(self.response.body, Exception)
         return self.response.body
 
     def on_response(self, response_handler):
@@ -889,13 +894,13 @@ class Response(Message):
     the appropriate exception type that applies_to() the Response object.
     """
 
-    def __init__(self, channel, seq, request, body, json=None):
+    def __init__(self, channel, seq, request, body: MessageDict | Exception, json=None):
         super().__init__(channel, seq, json)
 
         self.request = request
         """The request to which this is the response."""
 
-        if is_associatable(body):
+        if is_associable(body):
             body.associate_with(self)
         self.body = body
         """Body of the response if the request was successful, or an instance
@@ -1366,7 +1371,7 @@ class JsonMessageChannel(object):
         # for all JSON objects, and track them so that they can be later wired up to
         # the Message they belong to, once it is instantiated.
         def object_hook(d):
-            d = AssociatableMessageDict(None, d)
+            d = AssociableMessageDict(None, d)
             if "seq" in d:
                 self._prettify(d)
             setattr(d, "associate_with", associate_with)
diff --git a/src/debugpy/common/singleton.py b/src/debugpy/common/singleton.py
index f8da9ec3..f3f9abf8 100644
--- a/src/debugpy/common/singleton.py
+++ b/src/debugpy/common/singleton.py
@@ -141,9 +141,9 @@ class ThreadSafeSingleton(Singleton):
     # with @threadsafe_method. Such methods should perform the necessary locking to
     # ensure thread safety for the callers.
 
-    @staticmethod
-    def assert_locked(self): # type: ignore
+    def assert_locked(self):
         lock = type(self)._lock
+        assert lock is not None
         assert lock.acquire(blocking=False), (
             "ThreadSafeSingleton accessed without locking. Either use with-statement, "
             "or if it is a method or property, mark it as @threadsafe_method or with "
diff --git a/src/debugpy/common/sockets.py b/src/debugpy/common/sockets.py
index 7b26026a..202bbbe7 100644
--- a/src/debugpy/common/sockets.py
+++ b/src/debugpy/common/sockets.py
@@ -5,7 +5,7 @@
 import socket
 import sys
 import threading
-from typing import Callable, Union
+from typing import Any, Callable, Union
 
 from debugpy.common import log
 from debugpy.common.util import hide_thread_from_debugger
@@ -89,7 +89,7 @@ def close_socket(sock):
     sock.close()
 
 
-def serve(name: str, handler: Callable[[socket.socket], None], host: str, port: int=0, backlog=socket.SOMAXCONN, timeout: Union[int, None]=None):
+def serve(name: str, handler: Callable[[socket.socket], Any], host: str, port: int=0, backlog=socket.SOMAXCONN, timeout: Union[int, None]=None):
     """Accepts TCP connections on the specified host and port, and invokes the
     provided handler function for every new connection.
 
diff --git a/src/debugpy/launcher/debuggee.py b/src/debugpy/launcher/debuggee.py
index 4b6ac87c..e5dc7206 100644
--- a/src/debugpy/launcher/debuggee.py
+++ b/src/debugpy/launcher/debuggee.py
@@ -91,7 +91,7 @@ def spawn(process_name, cmdline, env, redirect_output):
 
         try:
             global process
-            process = subprocess.Popen(cmdline, env=env, bufsize=0, **kwargs) # type: ignore
+            process = subprocess.Popen(cmdline, env=env, bufsize=0, **kwargs)
         except Exception as exc:
             raise messaging.MessageHandlingError(
                 "Couldn't spawn debuggee: {0}\n\nCommand line:{1!r}".format(
@@ -244,7 +244,7 @@ def _wait_for_user_input():
             log.debug("msvcrt available - waiting for user input via getch()")
             sys.stdout.write("Press any key to continue . . . ")
             sys.stdout.flush()
-            msvcrt.getch() # type: ignore
+            msvcrt.getch() # pyright: ignore[reportPossiblyUnboundVariable, reportAttributeAccessIssue]
         else:
             log.debug("msvcrt not available - waiting for user input via read()")
             sys.stdout.write("Press Enter to continue . . . ")
diff --git a/src/debugpy/launcher/winapi.py b/src/debugpy/launcher/winapi.py
index e65d3ee9..4b470f5f 100644
--- a/src/debugpy/launcher/winapi.py
+++ b/src/debugpy/launcher/winapi.py
@@ -64,14 +64,14 @@ def _errcheck(is_error_result=(lambda result: not result)):
     def impl(result, func, args):
         if is_error_result(result):
             log.debug("{0} returned {1}", func.__name__, result)
-            raise ctypes.WinError() # type: ignore
+            raise ctypes.WinError() # pyright: ignore[reportAttributeAccessIssue]
         else:
             return result
 
     return impl
 
 
-kernel32 = ctypes.windll.kernel32 # type: ignore
+kernel32 = ctypes.windll.kernel32 # pyright: ignore[reportAttributeAccessIssue]
 
 kernel32.AssignProcessToJobObject.errcheck = _errcheck()
 kernel32.AssignProcessToJobObject.restype = BOOL
diff --git a/src/debugpy/server/api.py b/src/debugpy/server/api.py
index f1698142..6be27cf8 100644
--- a/src/debugpy/server/api.py
+++ b/src/debugpy/server/api.py
@@ -54,16 +54,16 @@ class _settrace():
 
 def ensure_logging():
     """Starts logging to log.log_dir, if it hasn't already been done."""
-    if ensure_logging.ensured: # type: ignore
+    if ensure_logging.ensured: # pyright: ignore[reportFunctionMemberAccess]
         return
-    ensure_logging.ensured = True # type: ignore
+    ensure_logging.ensured = True # pyright: ignore[reportFunctionMemberAccess]
     log.to_file(prefix="debugpy.server")
     log.describe_environment("Initial environment:")
     if log.log_dir is not None:
         pydevd.log_to(log.log_dir + "/debugpy.pydevd.log")
 
 
-ensure_logging.ensured = False # type: ignore
+ensure_logging.ensured = False # pyright: ignore[reportFunctionMemberAccess]
 
 
 def log_to(path):