diff --git a/certbot/src/certbot/_internal/account.py b/certbot/src/certbot/_internal/account.py
index 1c15a5ae6..548d2ae0b 100644
--- a/certbot/src/certbot/_internal/account.py
+++ b/certbot/src/certbot/_internal/account.py
@@ -8,8 +8,6 @@ import socket
 from typing import Any
 from typing import Callable
 from typing import cast
-from typing import Dict
-from typing import List
 from typing import Mapping
 from typing import Optional
 
@@ -107,10 +105,10 @@ class Account:
 class AccountMemoryStorage(interfaces.AccountStorage):
     """In-memory account storage."""
 
-    def __init__(self, initial_accounts: Optional[Dict[str, Account]] = None) -> None:
+    def __init__(self, initial_accounts: Optional[dict[str, Account]] = None) -> None:
         self.accounts = initial_accounts if initial_accounts is not None else {}
 
-    def find_all(self) -> List[Account]:
+    def find_all(self) -> list[Account]:
         return list(self.accounts.values())
 
     def save(self, account: Account, client: ClientV2) -> None:
@@ -154,7 +152,7 @@ class AccountFileStorage(interfaces.AccountStorage):
     def _metadata_path(cls, account_dir_path: str) -> str:
         return os.path.join(account_dir_path, "meta.json")
 
-    def _find_all_for_server_path(self, server_path: str) -> List[Account]:
+    def _find_all_for_server_path(self, server_path: str) -> list[Account]:
         accounts_dir = self.config.accounts_dir_for_server_path(server_path)
         try:
             candidates = os.listdir(accounts_dir)
@@ -181,7 +179,7 @@ class AccountFileStorage(interfaces.AccountStorage):
             accounts = prev_accounts
         return accounts
 
-    def find_all(self) -> List[Account]:
+    def find_all(self) -> list[Account]:
         return self._find_all_for_server_path(self.config.server_path)
 
     def _symlink_to_account_dir(self, prev_server_path: str, server_path: str,
diff --git a/certbot/src/certbot/_internal/auth_handler.py b/certbot/src/certbot/_internal/auth_handler.py
index 17b91053f..099512bc4 100644
--- a/certbot/src/certbot/_internal/auth_handler.py
+++ b/certbot/src/certbot/_internal/auth_handler.py
@@ -2,13 +2,9 @@
 import datetime
 import logging
 import time
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Optional
 from typing import Sequence
-from typing import Tuple
-from typing import Type
 
 import josepy
 from requests.models import Response
@@ -46,7 +42,7 @@ class AuthHandler:
 
     """
     def __init__(self, auth: interfaces.Authenticator, acme_client: Optional[client.ClientV2],
-                 account: Optional[Account], pref_challs: List[str]) -> None:
+                 account: Optional[Account], pref_challs: list[str]) -> None:
         self.auth = auth
         self.acme = acme_client
 
@@ -56,7 +52,7 @@ class AuthHandler:
     def handle_authorizations(self, orderr: messages.OrderResource,
                               config: configuration.NamespaceConfig, best_effort: bool = False,
                               max_retries: int = 30,
-                              max_time_mins: float = 30) -> List[messages.AuthorizationResource]:
+                              max_time_mins: float = 30) -> list[messages.AuthorizationResource]:
         """
         Retrieve all authorizations, perform all challenges required to validate
         these authorizations, then poll and wait for the authorization to be checked.
@@ -117,7 +113,7 @@ class AuthHandler:
 
         raise errors.Error("An unexpected error occurred while handling the authorizations.")
 
-    def deactivate_valid_authorizations(self, orderr: messages.OrderResource) -> Tuple[List, List]:
+    def deactivate_valid_authorizations(self, orderr: messages.OrderResource) -> tuple[list, list]:
         """
         Deactivate all `valid` authorizations in the order, so that they cannot be reused
         in subsequent orders.
@@ -144,7 +140,7 @@ class AuthHandler:
 
         return (deactivated, failed)
 
-    def _poll_authorizations(self, authzrs: List[messages.AuthorizationResource], max_retries: int,
+    def _poll_authorizations(self, authzrs: list[messages.AuthorizationResource], max_retries: int,
                              deadline_minutes: float, best_effort: bool) -> None:
         """
         Poll the ACME CA server, to wait for confirmation that authorizations have their challenges
@@ -154,7 +150,7 @@ class AuthHandler:
         if not self.acme:
             raise errors.Error("No ACME client defined, cannot poll authorizations.")
 
-        authzrs_to_check: Dict[int, Tuple[messages.AuthorizationResource,
+        authzrs_to_check: dict[int, tuple[messages.AuthorizationResource,
                                           Optional[Response]]] = {index: (authzr, None)
                             for index, authzr in enumerate(authzrs)}
         authzrs_failed_to_report = []
@@ -216,7 +212,7 @@ class AuthHandler:
             raise errors.AuthorizationError('All authorizations were not finalized by the CA.')
 
     def _choose_challenges(self, authzrs: Iterable[messages.AuthorizationResource]
-                           ) -> List[achallenges.AnnotatedChallenge]:
+                           ) -> list[achallenges.AnnotatedChallenge]:
         """
         Retrieve necessary and pending challenges to satisfy server.
         NB: Necessary and already validated challenges are not retrieved,
@@ -227,7 +223,7 @@ class AuthHandler:
 
         pending_authzrs = [authzr for authzr in authzrs
                            if authzr.body.status != messages.STATUS_VALID]
-        achalls: List[achallenges.AnnotatedChallenge] = []
+        achalls: list[achallenges.AnnotatedChallenge] = []
         if pending_authzrs:
             logger.info("Performing the following challenges:")
         for authzr in pending_authzrs:
@@ -241,7 +237,7 @@ class AuthHandler:
 
         return achalls
 
-    def _get_chall_pref(self, domain: str) -> List[Type[challenges.Challenge]]:
+    def _get_chall_pref(self, domain: str) -> list[type[challenges.Challenge]]:
         """Return list of challenge preferences.
 
         :param str domain: domain for which you are requesting preferences
@@ -263,7 +259,7 @@ class AuthHandler:
         chall_prefs.extend(plugin_pref)
         return chall_prefs
 
-    def _cleanup_challenges(self, achalls: List[achallenges.AnnotatedChallenge]) -> None:
+    def _cleanup_challenges(self, achalls: list[achallenges.AnnotatedChallenge]) -> None:
         """Cleanup challenges.
 
         :param achalls: annotated challenges to cleanup
@@ -274,7 +270,7 @@ class AuthHandler:
         self.auth.cleanup(achalls)
 
     def _challenge_factory(self, authzr: messages.AuthorizationResource,
-                           path: Sequence[int]) -> List[achallenges.AnnotatedChallenge]:
+                           path: Sequence[int]) -> list[achallenges.AnnotatedChallenge]:
         """Construct Namedtuple Challenges
 
         :param messages.AuthorizationResource authzr: authorization
@@ -299,11 +295,11 @@ class AuthHandler:
 
         return achalls
 
-    def _report_failed_authzrs(self, failed_authzrs: List[messages.AuthorizationResource]) -> None:
+    def _report_failed_authzrs(self, failed_authzrs: list[messages.AuthorizationResource]) -> None:
         """Notifies the user about failed authorizations."""
         if not self.account:
             raise errors.Error("Account is not set.")
-        problems: Dict[str, List[achallenges.AnnotatedChallenge]] = {}
+        problems: dict[str, list[achallenges.AnnotatedChallenge]] = {}
         failed_achalls = [challb_to_achall(challb, self.account.key, authzr.body.identifier.value)
                         for authzr in failed_authzrs for challb in authzr.body.challenges
                         if challb.error]
@@ -325,7 +321,7 @@ class AuthHandler:
 
         display_util.notify("".join(msg))
 
-    def _debug_challenges_msg(self, achalls: List[achallenges.AnnotatedChallenge],
+    def _debug_challenges_msg(self, achalls: list[achallenges.AnnotatedChallenge],
                               config: configuration.NamespaceConfig) -> str:
         """Construct message for debug challenges prompt
 
@@ -388,8 +384,8 @@ def challb_to_achall(challb: messages.ChallengeBody, account_key: josepy.JWK,
         return achallenges.Other(challb=challb, domain=domain)
 
 
-def gen_challenge_path(challbs: List[messages.ChallengeBody],
-                       preferences: List[Type[challenges.Challenge]]) -> Tuple[int, ...]:
+def gen_challenge_path(challbs: list[messages.ChallengeBody],
+                       preferences: list[type[challenges.Challenge]]) -> tuple[int, ...]:
     """Generate a plan to get authority over the identity.
 
     :param tuple challbs: A tuple of challenges
@@ -417,7 +413,7 @@ def gen_challenge_path(challbs: List[messages.ChallengeBody],
 
     # max_cost is now equal to sum(indices) + 1
 
-    best_combo: Optional[Tuple[int, ...]] = None
+    best_combo: Optional[tuple[int, ...]] = None
     # Set above completing all of the available challenges
     best_combo_cost = max_cost
 
@@ -441,7 +437,7 @@ def gen_challenge_path(challbs: List[messages.ChallengeBody],
     return best_combo
 
 
-def _report_no_chall_path(challbs: List[messages.ChallengeBody]) -> errors.AuthorizationError:
+def _report_no_chall_path(challbs: list[messages.ChallengeBody]) -> errors.AuthorizationError:
     """Logs and return a raisable error reporting that no satisfiable chall path exists.
 
     :param challbs: challenges from the authorization that can't be satisfied
@@ -460,7 +456,7 @@ def _report_no_chall_path(challbs: List[messages.ChallengeBody]) -> errors.Autho
     return errors.AuthorizationError(msg)
 
 
-def _generate_failed_chall_msg(failed_achalls: List[achallenges.AnnotatedChallenge]) -> str:
+def _generate_failed_chall_msg(failed_achalls: list[achallenges.AnnotatedChallenge]) -> str:
     """Creates a user friendly error message about failed challenges.
 
     :param list failed_achalls: A list of failed
diff --git a/certbot/src/certbot/_internal/cert_manager.py b/certbot/src/certbot/_internal/cert_manager.py
index 1510db21f..17e885d53 100644
--- a/certbot/src/certbot/_internal/cert_manager.py
+++ b/certbot/src/certbot/_internal/cert_manager.py
@@ -6,9 +6,7 @@ import traceback
 from typing import Any
 from typing import Callable
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
 from typing import TypeVar
 from typing import Union
 
@@ -122,14 +120,14 @@ def lineage_for_certname(cli_config: configuration.NamespaceConfig,
 
 
 def domains_for_certname(config: configuration.NamespaceConfig,
-                         certname: str) -> Optional[List[str]]:
+                         certname: str) -> Optional[list[str]]:
     """Find the domains in the cert with name certname."""
     lineage = lineage_for_certname(config, certname)
     return lineage.names() if lineage else None
 
 
 def find_duplicative_certs(config: configuration.NamespaceConfig,
-                           domains: List[str]) -> Tuple[Optional[storage.RenewableCert],
+                           domains: list[str]) -> tuple[Optional[storage.RenewableCert],
                                                         Optional[storage.RenewableCert]]:
     """Find existing certs that match the given domain names.
 
@@ -154,9 +152,9 @@ def find_duplicative_certs(config: configuration.NamespaceConfig,
 
     """
     def update_certs_for_domain_matches(candidate_lineage: storage.RenewableCert,
-                                        rv: Tuple[Optional[storage.RenewableCert],
+                                        rv: tuple[Optional[storage.RenewableCert],
                                                   Optional[storage.RenewableCert]]
-                                        ) -> Tuple[Optional[storage.RenewableCert],
+                                        ) -> tuple[Optional[storage.RenewableCert],
                                                    Optional[storage.RenewableCert]]:
         """Return cert as identical_names_cert if it matches,
            or subset_names_cert if it matches as subset
@@ -176,12 +174,12 @@ def find_duplicative_certs(config: configuration.NamespaceConfig,
                 subset_names_cert = candidate_lineage
         return (identical_names_cert, subset_names_cert)
 
-    init: Tuple[Optional[storage.RenewableCert], Optional[storage.RenewableCert]] = (None, None)
+    init: tuple[Optional[storage.RenewableCert], Optional[storage.RenewableCert]] = (None, None)
 
     return _search_lineages(config, update_certs_for_domain_matches, init)
 
 
-def _archive_files(candidate_lineage: storage.RenewableCert, filetype: str) -> Optional[List[str]]:
+def _archive_files(candidate_lineage: storage.RenewableCert, filetype: str) -> Optional[list[str]]:
     """ In order to match things like:
         /etc/letsencrypt/archive/example.com/chain1.pem.
 
@@ -203,8 +201,8 @@ def _archive_files(candidate_lineage: storage.RenewableCert, filetype: str) -> O
     return None
 
 
-def _acceptable_matches() -> List[Union[Callable[[storage.RenewableCert], str],
-                                        Callable[[storage.RenewableCert], Optional[List[str]]]]]:
+def _acceptable_matches() -> list[Union[Callable[[storage.RenewableCert], str],
+                                        Callable[[storage.RenewableCert], Optional[list[str]]]]]:
     """ Generates the list that's passed to match_and_check_overlaps. Is its own function to
     make unit testing easier.
 
@@ -235,9 +233,9 @@ def cert_path_to_lineage(cli_config: configuration.NamespaceConfig) -> str:
 def match_and_check_overlaps(cli_config: configuration.NamespaceConfig,
                              acceptable_matches: Iterable[Union[
                                  Callable[[storage.RenewableCert], str],
-                                 Callable[[storage.RenewableCert], Optional[List[str]]]]],
+                                 Callable[[storage.RenewableCert], Optional[list[str]]]]],
                              match_func: Callable[[storage.RenewableCert], str],
-                             rv_func: Callable[[storage.RenewableCert], str]) -> List[str]:
+                             rv_func: Callable[[storage.RenewableCert], str]) -> list[str]:
     """ Searches through all lineages for a match, and checks for duplicates.
     If a duplicate is found, an error is raised, as performing operations on lineages
     that have their properties incorrectly duplicated elsewhere is probably a bad idea.
@@ -248,13 +246,13 @@ def match_and_check_overlaps(cli_config: configuration.NamespaceConfig,
     :param function rv_func: specifies what to return
 
     """
-    def find_matches(candidate_lineage: storage.RenewableCert, return_value: List[str],
+    def find_matches(candidate_lineage: storage.RenewableCert, return_value: list[str],
                      acceptable_matches: Iterable[Union[
                          Callable[[storage.RenewableCert], str],
-                         Callable[[storage.RenewableCert], Optional[List[str]]]]]) -> List[str]:
+                         Callable[[storage.RenewableCert], Optional[list[str]]]]]) -> list[str]:
         """Returns a list of matches using _search_lineages."""
         acceptable_matches_resolved = [func(candidate_lineage) for func in acceptable_matches]
-        acceptable_matches_rv: List[str] = []
+        acceptable_matches_rv: list[str] = []
         for item in acceptable_matches_resolved:
             if isinstance(item, list):
                 acceptable_matches_rv += item
@@ -265,7 +263,7 @@ def match_and_check_overlaps(cli_config: configuration.NamespaceConfig,
             return_value.append(rv_func(candidate_lineage))
         return return_value
 
-    matched: List[str] = _search_lineages(cli_config, find_matches, [], acceptable_matches)
+    matched: list[str] = _search_lineages(cli_config, find_matches, [], acceptable_matches)
     if not matched:
         raise errors.Error(f"No match found for cert-path {cli_config.cert_path}!")
     elif len(matched) > 1:
@@ -317,7 +315,7 @@ def human_readable_cert_info(config: configuration.NamespaceConfig, cert: storag
 
 
 def get_certnames(config: configuration.NamespaceConfig, verb: str, allow_multiple: bool = False,
-                  custom_prompt: Optional[str] = None) -> List[str]:
+                  custom_prompt: Optional[str] = None) -> list[str]:
     """Get certname from flag, interactively, or error out."""
     certname = config.certname
     if certname:
@@ -375,7 +373,7 @@ def _describe_certs(config: configuration.NamespaceConfig,
                     parsed_certs: Iterable[storage.RenewableCert],
                     parse_failures: Iterable[str]) -> None:
     """Print information about the certs we know about"""
-    out: List[str] = []
+    out: list[str] = []
 
     notify = out.append
 
diff --git a/certbot/src/certbot/_internal/cli/__init__.py b/certbot/src/certbot/_internal/cli/__init__.py
index 31964153f..d5910b654 100644
--- a/certbot/src/certbot/_internal/cli/__init__.py
+++ b/certbot/src/certbot/_internal/cli/__init__.py
@@ -56,7 +56,7 @@ logger = logging.getLogger(__name__)
 helpful_parser: Optional[HelpfulArgumentParser] = None
 
 
-def prepare_and_parse_args(plugins: plugins_disco.PluginsRegistry, args: List[str]
+def prepare_and_parse_args(plugins: plugins_disco.PluginsRegistry, args: list[str]
                            ) -> NamespaceConfig:
     """Returns parsed command line arguments.
 
@@ -491,7 +491,7 @@ def prepare_and_parse_args(plugins: plugins_disco.PluginsRegistry, args: List[st
     return helpful.parse_args()
 
 
-def argparse_type(variable: Any) -> Type:
+def argparse_type(variable: Any) -> type:
     """Return our argparse type function for a config variable (default: str)"""
     # pylint: disable=protected-access
     if helpful_parser is not None:
diff --git a/certbot/src/certbot/_internal/cli/cli_utils.py b/certbot/src/certbot/_internal/cli/cli_utils.py
index 5cb0672b9..e3900ee43 100644
--- a/certbot/src/certbot/_internal/cli/cli_utils.py
+++ b/certbot/src/certbot/_internal/cli/cli_utils.py
@@ -5,10 +5,8 @@ import glob
 import inspect
 from typing import Any
 from typing import Iterable
-from typing import List
 from typing import Optional
 from typing import Sequence
-from typing import Tuple
 from typing import TYPE_CHECKING
 from typing import Union
 
@@ -23,7 +21,7 @@ if TYPE_CHECKING:
     from certbot._internal.cli import helpful
 
 
-def read_file(filename: str, mode: str = "rb") -> Tuple[str, Any]:
+def read_file(filename: str, mode: str = "rb") -> tuple[str, Any]:
     """Returns the given file's contents.
 
     :param str filename: path to file
@@ -105,7 +103,7 @@ class _DomainsAction(argparse.Action):
 
 
 def add_domains(args_or_config: Union[argparse.Namespace, configuration.NamespaceConfig],
-                domains: Optional[str]) -> List[str]:
+                domains: Optional[str]) -> list[str]:
     """Registers new domains to be used during the current client run.
 
     Domains are not added to the list of requested domains if they have
@@ -120,7 +118,7 @@ def add_domains(args_or_config: Union[argparse.Namespace, configuration.Namespac
     :rtype: `list` of `str`
 
     """
-    validated_domains: List[str] = []
+    validated_domains: list[str] = []
     if not domains:
         return validated_domains
 
@@ -164,7 +162,7 @@ class _EncodeReasonAction(argparse.Action):
         setattr(namespace, self.dest, code)
 
 
-def parse_preferred_challenges(pref_challs: Iterable[str]) -> List[str]:
+def parse_preferred_challenges(pref_challs: Iterable[str]) -> list[str]:
     """Translate and validate preferred challenges.
 
     :param pref_challs: list of preferred challenge types
diff --git a/certbot/src/certbot/_internal/cli/helpful.py b/certbot/src/certbot/_internal/cli/helpful.py
index a53e9edda..9a0097e53 100644
--- a/certbot/src/certbot/_internal/cli/helpful.py
+++ b/certbot/src/certbot/_internal/cli/helpful.py
@@ -4,11 +4,8 @@ import argparse
 import functools
 import sys
 from typing import Any
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
 from typing import Union
 
 import configargparse
@@ -42,7 +39,7 @@ class HelpfulArgumentParser:
     'certbot --help security' for security options.
 
     """
-    def __init__(self, args: List[str], plugins: Iterable[str]) -> None:
+    def __init__(self, args: list[str], plugins: Iterable[str]) -> None:
         from certbot._internal import main
         self.VERBS = {
             "auth": main.certonly,
@@ -67,14 +64,14 @@ class HelpfulArgumentParser:
         # Get notification function for printing
         self.notify = display_obj.NoninteractiveDisplay(sys.stdout).notification
 
-        self.actions: List[configargparse.Action] = []
+        self.actions: list[configargparse.Action] = []
 
         # List of topics for which additional help can be provided
-        HELP_TOPICS: List[Optional[str]] = ["all", "security", "paths", "automation", "testing"]
+        HELP_TOPICS: list[Optional[str]] = ["all", "security", "paths", "automation", "testing"]
         HELP_TOPICS += list(self.VERBS) + self.COMMANDS_TOPICS + ["manage"]
 
-        plugin_names: List[Optional[str]] = list(plugins)
-        self.help_topics: List[Optional[str]] = HELP_TOPICS + plugin_names + [None]
+        plugin_names: list[Optional[str]] = list(plugins)
+        self.help_topics: list[Optional[str]] = HELP_TOPICS + plugin_names + [None]
 
         self.args = args
 
@@ -95,7 +92,7 @@ class HelpfulArgumentParser:
         self.visible_topics = self.determine_help_topics(self.help_arg)
 
         # elements are added by .add_group()
-        self.groups: Dict[str, argparse._ArgumentGroup] = {}
+        self.groups: dict[str, argparse._ArgumentGroup] = {}
 
         self.parser = configargparse.ArgParser(
             prog="certbot",
@@ -168,7 +165,7 @@ class HelpfulArgumentParser:
                 self.verb == "renew"):
             config.domains = []
 
-    def _build_sources_dict(self) -> Dict[str, ArgumentSource]:
+    def _build_sources_dict(self) -> dict[str, ArgumentSource]:
         # ConfigArgparse's get_source_to_settings_dict doesn't actually create
         # default entries for each argument with a default value, omitting many
         # args we'd otherwise care about. So in general, unless an argument was
@@ -176,7 +173,7 @@ class HelpfulArgumentParser:
         # consider it as having a "default" value
         result = { action.dest: ArgumentSource.DEFAULT for action in self.actions }
 
-        source_to_settings_dict: Dict[str, Dict[str, Tuple[configargparse.Action, str]]]
+        source_to_settings_dict: dict[str, dict[str, tuple[configargparse.Action, str]]]
         source_to_settings_dict = self.parser.get_source_to_settings_dict()
 
         # We'll process the sources dict in order of each source's "priority",
@@ -187,7 +184,7 @@ class HelpfulArgumentParser:
         #   3. env vars (shouldn't be any)
         #   4. command line
 
-        def update_result(settings_dict: Dict[str, Tuple[configargparse.Action, str]],
+        def update_result(settings_dict: dict[str, tuple[configargparse.Action, str]],
                           source: ArgumentSource) -> None:
             actions = [self._find_action_for_arg(arg) if action is None else action
                        for arg, (action, _) in settings_dict.items()]
@@ -202,7 +199,7 @@ class HelpfulArgumentParser:
 
         # The command line settings dict is weird, so handle it separately
         if 'command_line' in source_to_settings_dict:
-            settings_dict: Dict[str, Tuple[None, List[str]]]
+            settings_dict: dict[str, tuple[None, list[str]]]
             settings_dict = source_to_settings_dict['command_line'] # type: ignore
             (_, unprocessed_args) = settings_dict['']
             args = []
@@ -401,7 +398,7 @@ class HelpfulArgumentParser:
             pass
         return True
 
-    def add(self, topics: Optional[Union[List[Optional[str]], str]], *args: Any,
+    def add(self, topics: Optional[Union[list[Optional[str]], str]], *args: Any,
             **kwargs: Any) -> None:
         """Add a new command line argument.
 
@@ -416,7 +413,7 @@ class HelpfulArgumentParser:
         """
         self.actions.append(self._add(topics, *args, **kwargs))
 
-    def _add(self, topics: Optional[Union[List[Optional[str]], str]], *args: Any,
+    def _add(self, topics: Optional[Union[list[Optional[str]], str]], *args: Any,
             **kwargs: Any) -> configargparse.Action:
         action = kwargs.get("action")
         if action is util.DeprecatedArgumentAction:
@@ -511,7 +508,7 @@ class HelpfulArgumentParser:
             plugin_ep.plugin_cls.inject_parser_options(parser_or_group, name)
 
     def determine_help_topics(self, chosen_topic: Union[str, bool]
-                              ) -> Dict[Optional[str], bool]:
+                              ) -> dict[Optional[str], bool]:
         """
 
         The user may have requested help on a topic, return a dict of which
diff --git a/certbot/src/certbot/_internal/client.py b/certbot/src/certbot/_internal/client.py
index 0bc4cae04..2a0e256c8 100644
--- a/certbot/src/certbot/_internal/client.py
+++ b/certbot/src/certbot/_internal/client.py
@@ -5,11 +5,8 @@ import platform
 from typing import Any
 from typing import Callable
 from typing import cast
-from typing import Dict
 from typing import IO
-from typing import List
 from typing import Optional
-from typing import Tuple
 
 from cryptography import x509
 from cryptography.hazmat.backends import default_backend
@@ -152,7 +149,7 @@ def sample_user_agent() -> str:
 
 def register(config: configuration.NamespaceConfig, account_storage: AccountStorage,
              tos_cb: Optional[Callable[[str], None]] = None
-             ) -> Tuple[account.Account, acme_client.ClientV2]:
+             ) -> tuple[account.Account, acme_client.ClientV2]:
     """Register new account with an ACME CA.
 
     This function takes care of generating fresh private key,
@@ -232,7 +229,7 @@ def perform_registration(acme: acme_client.ClientV2, config: configuration.Names
         raise errors.Error("acme client with no private key cannot register account.")
 
     eab_credentials_supplied = config.eab_kid and config.eab_hmac_key
-    eab: Optional[Dict[str, Any]]
+    eab: Optional[dict[str, Any]]
     if eab_credentials_supplied:
         account_public_key = acme.net.key.public_key()
         eab = messages.ExternalAccountBinding.from_data(account_public_key=account_public_key,
@@ -308,7 +305,7 @@ class Client:
 
     def obtain_certificate_from_csr(self, csr: util.CSR,
                                     orderr: Optional[messages.OrderResource] = None
-                                    ) -> Tuple[bytes, bytes]:
+                                    ) -> tuple[bytes, bytes]:
         """Obtain certificate.
 
         :param .util.CSR csr: PEM-encoded Certificate Signing
@@ -351,8 +348,8 @@ class Client:
         cert, chain = crypto_util.cert_and_chain_from_fullchain(fullchain)
         return cert.encode(), chain.encode()
 
-    def obtain_certificate(self, domains: List[str], old_keypath: Optional[str] = None
-                           ) -> Tuple[bytes, bytes, util.Key, util.CSR]:
+    def obtain_certificate(self, domains: list[str], old_keypath: Optional[str] = None
+                           ) -> tuple[bytes, bytes, util.Key, util.CSR]:
         """Obtains a certificate from the ACME server.
 
         `.register` must be called before `.obtain_certificate`
@@ -508,7 +505,7 @@ class Client:
         authzr = self.auth_handler.handle_authorizations(orderr, self.config, best_effort)
         return orderr.update(authorizations=authzr)
 
-    def obtain_and_enroll_certificate(self, domains: List[str], certname: Optional[str]
+    def obtain_and_enroll_certificate(self, domains: list[str], certname: Optional[str]
                                       ) -> Optional[storage.RenewableCert]:
         """Obtain and enroll certificate.
 
@@ -542,8 +539,8 @@ class Client:
             key.pem, chain,
             self.config)
 
-    def _successful_domains_from_error(self, error: messages.Error, domains: List[str],
-                                ) -> List[str]:
+    def _successful_domains_from_error(self, error: messages.Error, domains: list[str],
+                                ) -> list[str]:
         if error.subproblems is not None:
             failed_domains = [problem.identifier.value for problem in error.subproblems
                                 if problem.identifier is not None]
@@ -551,16 +548,16 @@ class Client:
             return successful_domains
         return []
 
-    def _retry_obtain_certificate(self, domains: List[str], successful_domains: List[str],
+    def _retry_obtain_certificate(self, domains: list[str], successful_domains: list[str],
                                 old_keypath: Optional[str]
-                                ) -> Tuple[bytes, bytes, util.Key, util.CSR]:
+                                ) -> tuple[bytes, bytes, util.Key, util.CSR]:
         failed_domains = [d for d in domains if d not in successful_domains]
         domains_list = ", ".join(failed_domains)
         display_util.notify("Unable to obtain a certificate with every requested "
             f"domain. Retrying without: {domains_list}")
         return self.obtain_certificate(successful_domains, old_keypath)
 
-    def _choose_lineagename(self, domains: List[str], certname: Optional[str]) -> str:
+    def _choose_lineagename(self, domains: list[str], certname: Optional[str]) -> str:
         """Chooses a name for the new lineage.
 
         :param domains: domains in certificate request
@@ -609,7 +606,7 @@ class Client:
 
     def save_certificate(self, cert_pem: bytes, chain_pem: bytes,
                          cert_path: str, chain_path: str, fullchain_path: str
-                         ) -> Tuple[str, str, str]:
+                         ) -> tuple[str, str, str]:
         """Saves the certificate received from the ACME server.
 
         :param bytes cert_pem:
@@ -644,7 +641,7 @@ class Client:
 
         return abs_cert_path, abs_chain_path, abs_fullchain_path
 
-    def deploy_certificate(self, domains: List[str], privkey_path: str, cert_path: str,
+    def deploy_certificate(self, domains: list[str], privkey_path: str, cert_path: str,
                            chain_path: str, fullchain_path: str) -> None:
         """Install certificate
 
@@ -683,7 +680,7 @@ class Client:
             # sites may have been enabled / final cleanup
             self.installer.restart()
 
-    def enhance_config(self, domains: List[str], chain_path: str,
+    def enhance_config(self, domains: list[str], chain_path: str,
                        redirect_default: bool = True) -> None:
         """Enhance the configuration.
 
@@ -727,7 +724,7 @@ class Client:
             with error_handler.ErrorHandler(self._rollback_and_restart, msg):
                 self.installer.restart()
 
-    def apply_enhancement(self, domains: List[str], enhancement: str,
+    def apply_enhancement(self, domains: list[str], enhancement: str,
                           options: Optional[str] = None) -> None:
         """Applies an enhancement on all domains.
 
@@ -859,7 +856,7 @@ def rollback(default_installer: str, checkpoints: int,
 
 
 def _open_pem_file(config: configuration.NamespaceConfig,
-                   cli_arg_path: str, pem_path: str) -> Tuple[IO, str]:
+                   cli_arg_path: str, pem_path: str) -> tuple[IO, str]:
     """Open a pem file.
 
     If cli_arg_path was set by the client, open that.
diff --git a/certbot/src/certbot/_internal/constants.py b/certbot/src/certbot/_internal/constants.py
index 14f4d059a..4a2172c3e 100644
--- a/certbot/src/certbot/_internal/constants.py
+++ b/certbot/src/certbot/_internal/constants.py
@@ -4,7 +4,6 @@ import importlib.resources
 import logging
 from contextlib import ExitStack
 from typing import Any
-from typing import Dict
 
 from acme import challenges
 from certbot.compat import misc
@@ -16,7 +15,7 @@ SETUPTOOLS_PLUGINS_ENTRY_POINT = "certbot.plugins"
 OLD_SETUPTOOLS_PLUGINS_ENTRY_POINT = "letsencrypt.plugins"
 """Plugins Setuptools entry point before rename."""
 
-CLI_DEFAULTS: Dict[str, Any] = dict(  # pylint: disable=use-dict-literal
+CLI_DEFAULTS: dict[str, Any] = dict(  # pylint: disable=use-dict-literal
     config_files=[
         os.path.join(misc.get_default_folder('config'), 'cli.ini'),
         # https://freedesktop.org/wiki/Software/xdg-user-dirs/
diff --git a/certbot/src/certbot/_internal/display/completer.py b/certbot/src/certbot/_internal/display/completer.py
index 7d26f0875..ec440339d 100644
--- a/certbot/src/certbot/_internal/display/completer.py
+++ b/certbot/src/certbot/_internal/display/completer.py
@@ -5,7 +5,6 @@ from typing import Callable
 from typing import Iterator
 from typing import Literal
 from typing import Optional
-from typing import Type
 
 # readline module is not available on all systems
 try:
@@ -65,7 +64,7 @@ class Completer:
         else:
             readline.parse_and_bind('tab: complete')
 
-    def __exit__(self, unused_type: Optional[Type[BaseException]],
+    def __exit__(self, unused_type: Optional[type[BaseException]],
                  unused_value: Optional[BaseException],
                  unused_traceback: Optional[TracebackType]) -> 'Literal[False]':
         readline.set_completer_delims(self._original_delims)
diff --git a/certbot/src/certbot/_internal/display/dummy_readline.py b/certbot/src/certbot/_internal/display/dummy_readline.py
index 62152b050..0575a68cd 100644
--- a/certbot/src/certbot/_internal/display/dummy_readline.py
+++ b/certbot/src/certbot/_internal/display/dummy_readline.py
@@ -1,7 +1,6 @@
 """A dummy module with no effect for use on systems without readline."""
 from typing import Callable
 from typing import Iterable
-from typing import List
 from typing import Optional
 
 
@@ -9,7 +8,7 @@ def get_completer() -> Optional[Callable[[], str]]:
     """An empty implementation of readline.get_completer."""
 
 
-def get_completer_delims() -> List[str]:
+def get_completer_delims() -> list[str]:
     """An empty implementation of readline.get_completer_delims."""
     return []
 
diff --git a/certbot/src/certbot/_internal/display/obj.py b/certbot/src/certbot/_internal/display/obj.py
index 02fcd4cd1..8e8978ca1 100644
--- a/certbot/src/certbot/_internal/display/obj.py
+++ b/certbot/src/certbot/_internal/display/obj.py
@@ -3,10 +3,8 @@ import logging
 import sys
 from typing import Any
 from typing import Iterable
-from typing import List
 from typing import Optional
 from typing import TextIO
-from typing import Tuple
 from typing import TypeVar
 from typing import Union
 
@@ -90,11 +88,11 @@ class FileDisplay:
             else:
                 logger.debug("Not pausing for user confirmation")
 
-    def menu(self, message: str, choices: Union[List[Tuple[str, str]], List[str]],
+    def menu(self, message: str, choices: Union[list[tuple[str, str]], list[str]],
              ok_label: Optional[str] = None, cancel_label: Optional[str] = None,  # pylint: disable=unused-argument
              help_label: Optional[str] = None, default: Optional[int] = None,  # pylint: disable=unused-argument
              cli_flag: Optional[str] = None, force_interactive: bool = False,
-             **unused_kwargs: Any) -> Tuple[str, int]:
+             **unused_kwargs: Any) -> tuple[str, int]:
         """Display a menu.
 
         .. todo:: This doesn't enable the help label/button (I wasn't sold on
@@ -127,7 +125,7 @@ class FileDisplay:
         return code, selection - 1
 
     def input(self, message: str, default: Optional[str] = None, cli_flag: Optional[str] = None,
-              force_interactive: bool = False, **unused_kwargs: Any) -> Tuple[str, str]:
+              force_interactive: bool = False, **unused_kwargs: Any) -> tuple[str, str]:
         """Accept input from the user.
 
         :param str message: message to display to the user
@@ -199,9 +197,9 @@ class FileDisplay:
                 ans.startswith(no_label[0].upper())):
                 return False
 
-    def checklist(self, message: str, tags: List[str], default: Optional[List[str]] = None,
+    def checklist(self, message: str, tags: list[str], default: Optional[list[str]] = None,
                   cli_flag: Optional[str] = None, force_interactive: bool = False,
-                  **unused_kwargs: Any) -> Tuple[str, List[str]]:
+                  **unused_kwargs: Any) -> tuple[str, list[str]]:
         """Display a checklist.
 
         :param str message: Message to display to user
@@ -294,7 +292,7 @@ class FileDisplay:
 
     def directory_select(self, message: str, default: Optional[str] = None,
                          cli_flag: Optional[str] = None, force_interactive: bool = False,
-                         **unused_kwargs: Any) -> Tuple[str, str]:
+                         **unused_kwargs: Any) -> tuple[str, str]:
         """Display a directory selection screen.
 
         :param str message: prompt to give the user
@@ -312,7 +310,7 @@ class FileDisplay:
             return self.input(message, default, cli_flag, force_interactive)
 
     def _scrub_checklist_input(self, indices: Iterable[Union[str, int]],
-                               tags: List[str]) -> List[str]:
+                               tags: list[str]) -> list[str]:
         """Validate input and transform indices to appropriate tags.
 
         :param list indices: input
@@ -340,7 +338,7 @@ class FileDisplay:
         return [tags[index - 1] for index in indices_int]
 
     def _print_menu(self, message: str,
-                    choices: Union[List[Tuple[str, str]], List[str]]) -> None:
+                    choices: Union[list[tuple[str, str]], list[str]]) -> None:
         """Print a menu on the screen.
 
         :param str message: title of menu
@@ -368,7 +366,7 @@ class FileDisplay:
         self.outfile.write(SIDE_FRAME + os.linesep)
         self.outfile.flush()
 
-    def _get_valid_int_ans(self, max_: int) -> Tuple[str, int]:
+    def _get_valid_int_ans(self, max_: int) -> tuple[str, int]:
         """Get a numerical selection.
 
         :param int max: The maximum entry (len of choices), must be positive
@@ -446,10 +444,10 @@ class NoninteractiveDisplay:
         )
         self.outfile.flush()
 
-    def menu(self, message: str, choices: Union[List[Tuple[str, str]], List[str]],
+    def menu(self, message: str, choices: Union[list[tuple[str, str]], list[str]],
              ok_label: Optional[str] = None, cancel_label: Optional[str] = None,
              help_label: Optional[str] = None, default: Optional[int] = None,
-             cli_flag: Optional[str] = None, **unused_kwargs: Any) -> Tuple[str, int]:
+             cli_flag: Optional[str] = None, **unused_kwargs: Any) -> tuple[str, int]:
         # pylint: disable=unused-argument
         """Avoid displaying a menu.
 
@@ -473,7 +471,7 @@ class NoninteractiveDisplay:
         return OK, default
 
     def input(self, message: str, default: Optional[str] = None, cli_flag: Optional[str] = None,
-              **unused_kwargs: Any) -> Tuple[str, str]:
+              **unused_kwargs: Any) -> tuple[str, str]:
         """Accept input from the user.
 
         :param str message: message to display to the user
@@ -506,8 +504,8 @@ class NoninteractiveDisplay:
             raise self._interaction_fail(message, cli_flag)
         return default
 
-    def checklist(self, message: str, tags: Iterable[str], default: Optional[List[str]] = None,
-                  cli_flag: Optional[str] = None, **unused_kwargs: Any) -> Tuple[str, List[str]]:
+    def checklist(self, message: str, tags: Iterable[str], default: Optional[list[str]] = None,
+                  cli_flag: Optional[str] = None, **unused_kwargs: Any) -> tuple[str, list[str]]:
         """Display a checklist.
 
         :param str message: Message to display to user
@@ -525,7 +523,7 @@ class NoninteractiveDisplay:
         return OK, default
 
     def directory_select(self, message: str, default: Optional[str] = None,
-                         cli_flag: Optional[str] = None, **unused_kwargs: Any) -> Tuple[str, str]:
+                         cli_flag: Optional[str] = None, **unused_kwargs: Any) -> tuple[str, str]:
         """Simulate prompting the user for a directory.
 
         This function returns default if it is not ``None``, otherwise,
diff --git a/certbot/src/certbot/_internal/display/util.py b/certbot/src/certbot/_internal/display/util.py
index 3cb20ac7a..5ba8dc191 100644
--- a/certbot/src/certbot/_internal/display/util.py
+++ b/certbot/src/certbot/_internal/display/util.py
@@ -1,7 +1,6 @@
 """Internal Certbot display utilities."""
 import sys
 import textwrap
-from typing import List
 from typing import Optional
 
 from acme import messages as acme_messages
@@ -69,7 +68,7 @@ def input_with_timeout(prompt: Optional[str] = None, timeout: float = 36000.0) -
     return line.rstrip('\n')
 
 
-def separate_list_input(input_: str) -> List[str]:
+def separate_list_input(input_: str) -> list[str]:
     """Separate a comma or space separated list.
 
     :param str input_: input from the user
@@ -84,7 +83,7 @@ def separate_list_input(input_: str) -> List[str]:
     return [str(string) for string in no_commas.split()]
 
 
-def summarize_domain_list(domains: List[str]) -> str:
+def summarize_domain_list(domains: list[str]) -> str:
     """Summarizes a list of domains in the format of:
         example.com.com and N more domains
     or if there is are only two domains:
diff --git a/certbot/src/certbot/_internal/error_handler.py b/certbot/src/certbot/_internal/error_handler.py
index 8b9bddc53..5c7fb7d6d 100644
--- a/certbot/src/certbot/_internal/error_handler.py
+++ b/certbot/src/certbot/_internal/error_handler.py
@@ -6,10 +6,7 @@ import traceback
 from types import TracebackType
 from typing import Any
 from typing import Callable
-from typing import Dict
-from typing import List
 from typing import Optional
-from typing import Type
 from typing import Union
 
 from certbot import errors
@@ -80,9 +77,9 @@ class ErrorHandler:
     def __init__(self, func: Callable[..., Any], *args: Any, **kwargs: Any) -> None:
         self.call_on_regular_exit = False
         self.body_executed = False
-        self.funcs: List[Callable[[], Any]] = []
-        self.prev_handlers: Dict[int, Union[int, None, Callable]] = {}
-        self.received_signals: List[int] = []
+        self.funcs: list[Callable[[], Any]] = []
+        self.prev_handlers: dict[int, Union[int, None, Callable]] = {}
+        self.received_signals: list[int] = []
         if func is not None:
             self.register(func, *args, **kwargs)
 
@@ -90,7 +87,7 @@ class ErrorHandler:
         self.body_executed = False
         self._set_signal_handlers()
 
-    def __exit__(self, exec_type: Optional[Type[BaseException]],
+    def __exit__(self, exec_type: Optional[type[BaseException]],
                  exec_value: Optional[BaseException],
                  trace: Optional[TracebackType]) -> bool:
         self.body_executed = True
diff --git a/certbot/src/certbot/_internal/hooks.py b/certbot/src/certbot/_internal/hooks.py
index f75ecd02e..28499ab11 100644
--- a/certbot/src/certbot/_internal/hooks.py
+++ b/certbot/src/certbot/_internal/hooks.py
@@ -1,10 +1,7 @@
 """Facilities for implementing hooks that call shell commands."""
 
 import logging
-from typing import Dict
-from typing import List
 from typing import Optional
-from typing import Set
 
 from certbot import configuration
 from certbot import errors
@@ -75,14 +72,14 @@ def pre_hook(config: configuration.NamespaceConfig) -> None:
     :param configuration.NamespaceConfig config: Certbot settings
 
     """
-    all_hooks: List[str] = (list_hooks(config.renewal_pre_hooks_dir) if config.directory_hooks
+    all_hooks: list[str] = (list_hooks(config.renewal_pre_hooks_dir) if config.directory_hooks
         else [])
     all_hooks += [config.pre_hook] if config.pre_hook else []
     for hook in all_hooks:
         _run_pre_hook_if_necessary(hook)
 
 
-executed_pre_hooks: Set[str] = set()
+executed_pre_hooks: set[str] = set()
 
 
 def _run_pre_hook_if_necessary(command: str) -> None:
@@ -103,7 +100,7 @@ def _run_pre_hook_if_necessary(command: str) -> None:
 
 def post_hook(
     config: configuration.NamespaceConfig,
-    renewed_domains: List[str]
+    renewed_domains: list[str]
 ) -> None:
 
     """Run post-hooks if defined.
@@ -123,7 +120,7 @@ def post_hook(
 
     """
 
-    all_hooks: List[str] = (list_hooks(config.renewal_post_hooks_dir) if config.directory_hooks
+    all_hooks: list[str] = (list_hooks(config.renewal_post_hooks_dir) if config.directory_hooks
         else [])
     all_hooks += [config.post_hook] if config.post_hook else []
     # In the "renew" case, we save these up to run at the end
@@ -150,7 +147,7 @@ def post_hook(
             )
 
 
-post_hooks: List[str] = []
+post_hooks: list[str] = []
 
 
 def _run_eventually(command: str) -> None:
@@ -166,7 +163,7 @@ def _run_eventually(command: str) -> None:
         post_hooks.append(command)
 
 
-def run_saved_post_hooks(renewed_domains: List[str], failed_domains: List[str]) -> None:
+def run_saved_post_hooks(renewed_domains: list[str], failed_domains: list[str]) -> None:
     """Run any post hooks that were saved up in the course of the 'renew' verb"""
 
     renewed_domains_str = ' '.join(renewed_domains)
@@ -192,7 +189,7 @@ def run_saved_post_hooks(renewed_domains: List[str], failed_domains: List[str])
         )
 
 
-def deploy_hook(config: configuration.NamespaceConfig, domains: List[str],
+def deploy_hook(config: configuration.NamespaceConfig, domains: list[str],
                 lineage_path: str) -> None:
     """Run post-issuance hook if defined.
 
@@ -207,7 +204,7 @@ def deploy_hook(config: configuration.NamespaceConfig, domains: List[str],
                          lineage_path, config.dry_run, config.run_deploy_hooks)
 
 
-def renew_hook(config: configuration.NamespaceConfig, domains: List[str],
+def renew_hook(config: configuration.NamespaceConfig, domains: list[str],
                lineage_path: str) -> None:
     """Run post-renewal hooks.
 
@@ -226,7 +223,7 @@ def renew_hook(config: configuration.NamespaceConfig, domains: List[str],
 
     """
     executed_hooks = set()
-    all_hooks: List[str] = (list_hooks(config.renewal_deploy_hooks_dir)if config.directory_hooks
+    all_hooks: list[str] = (list_hooks(config.renewal_deploy_hooks_dir)if config.directory_hooks
         else [])
     all_hooks += [config.renew_hook] if config.renew_hook else []
     for hook in all_hooks:
@@ -237,7 +234,7 @@ def renew_hook(config: configuration.NamespaceConfig, domains: List[str],
             executed_hooks.add(hook)
 
 
-def _run_deploy_hook(command: str, domains: List[str], lineage_path: str, dry_run: bool,
+def _run_deploy_hook(command: str, domains: list[str], lineage_path: str, dry_run: bool,
                      run_deploy_hooks: bool) -> None:
     """Run the specified deploy-hook (if not doing a dry run).
 
@@ -263,7 +260,7 @@ def _run_deploy_hook(command: str, domains: List[str], lineage_path: str, dry_ru
     _run_hook("deploy-hook", command)
 
 
-def _run_hook(cmd_name: str, shell_cmd: str, extra_env: Optional[Dict[str, str]] = None) -> str:
+def _run_hook(cmd_name: str, shell_cmd: str, extra_env: Optional[dict[str, str]] = None) -> str:
     """Run a hook command.
 
     :param str cmd_name: the user facing name of the hook being run
@@ -281,7 +278,7 @@ def _run_hook(cmd_name: str, shell_cmd: str, extra_env: Optional[Dict[str, str]]
     return err
 
 
-def list_hooks(dir_path: str) -> List[str]:
+def list_hooks(dir_path: str) -> list[str]:
     """List paths to all hooks found in dir_path in sorted order.
 
     :param str dir_path: directory to search
diff --git a/certbot/src/certbot/_internal/log.py b/certbot/src/certbot/_internal/log.py
index 5a10c9fcb..2c3a7de38 100644
--- a/certbot/src/certbot/_internal/log.py
+++ b/certbot/src/certbot/_internal/log.py
@@ -33,8 +33,6 @@ from typing import Any
 from typing import cast
 from typing import IO
 from typing import Optional
-from typing import Tuple
-from typing import Type
 
 from acme import messages
 from certbot import configuration
@@ -148,7 +146,7 @@ def post_arg_parse_setup(config: configuration.NamespaceConfig) -> None:
 
 
 def setup_log_file_handler(config: configuration.NamespaceConfig, logfile: str,
-                           fmt: str) -> Tuple[logging.Handler, str]:
+                           fmt: str) -> tuple[logging.Handler, str]:
     """Setup file debug logging.
 
     :param certbot.configuration.NamespaceConfig config: Configuration object
@@ -332,7 +330,7 @@ def pre_arg_parse_except_hook(memory_handler: MemoryHandler,
         memory_handler.flush(force=True)
 
 
-def post_arg_parse_except_hook(exc_type: Type[BaseException], exc_value: BaseException,
+def post_arg_parse_except_hook(exc_type: type[BaseException], exc_value: BaseException,
                                trace: TracebackType, debug: bool, quiet: bool,
                                log_path: str) -> None:
     """Logs fatal exceptions and reports them to the user.
diff --git a/certbot/src/certbot/_internal/main.py b/certbot/src/certbot/_internal/main.py
index 92f2b5966..e26447be6 100644
--- a/certbot/src/certbot/_internal/main.py
+++ b/certbot/src/certbot/_internal/main.py
@@ -10,9 +10,7 @@ from typing import cast
 from typing import Generator
 from typing import IO
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
 from typing import TypeVar
 from typing import Union
 
@@ -87,7 +85,7 @@ def _suggest_donation_if_appropriate(config: configuration.NamespaceConfig) -> N
 
 
 def _get_and_save_cert(le_client: client.Client, config: configuration.NamespaceConfig,
-                       domains: Optional[List[str]] = None, certname: Optional[str] = None,
+                       domains: Optional[list[str]] = None, certname: Optional[str] = None,
                        lineage: Optional[storage.RenewableCert] = None
                        ) -> Optional[storage.RenewableCert]:
     """Authenticate and enroll certificate.
@@ -115,7 +113,7 @@ def _get_and_save_cert(le_client: client.Client, config: configuration.Namespace
 
     """
     hooks.pre_hook(config)
-    renewed_domains: List[str] = []
+    renewed_domains: list[str] = []
 
     try:
         if lineage is not None:
@@ -200,7 +198,7 @@ def _handle_unexpected_key_type_migration(config: configuration.NamespaceConfig,
 def _handle_subset_cert_request(config: configuration.NamespaceConfig,
                                 domains: Iterable[str],
                                 cert: storage.RenewableCert
-                                ) -> Tuple[str, Optional[storage.RenewableCert]]:
+                                ) -> tuple[str, Optional[storage.RenewableCert]]:
     """Figure out what to do if a previous cert had a subset of the names now requested
 
     :param config: Configuration object
@@ -247,7 +245,7 @@ def _handle_subset_cert_request(config: configuration.NamespaceConfig,
 
 def _handle_identical_cert_request(config: configuration.NamespaceConfig,
                                    lineage: storage.RenewableCert,
-                                   ) -> Tuple[str, Optional[storage.RenewableCert]]:
+                                   ) -> tuple[str, Optional[storage.RenewableCert]]:
     """Figure out what to do if a lineage has the same names as a previously obtained one
 
     :param config: Configuration object
@@ -305,8 +303,8 @@ def _handle_identical_cert_request(config: configuration.NamespaceConfig,
     raise AssertionError('This is impossible')
 
 
-def _find_lineage_for_domains(config: configuration.NamespaceConfig, domains: List[str]
-                              ) -> Tuple[Optional[str], Optional[storage.RenewableCert]]:
+def _find_lineage_for_domains(config: configuration.NamespaceConfig, domains: list[str]
+                              ) -> tuple[Optional[str], Optional[storage.RenewableCert]]:
     """Determine whether there are duplicated names and how to handle
     them (renew, reinstall, newcert, or raising an error to stop
     the client run if the user chooses to cancel the operation when
@@ -346,8 +344,8 @@ def _find_lineage_for_domains(config: configuration.NamespaceConfig, domains: Li
     return None, None
 
 
-def _find_cert(config: configuration.NamespaceConfig, domains: List[str], certname: str
-               ) -> Tuple[bool, Optional[storage.RenewableCert]]:
+def _find_cert(config: configuration.NamespaceConfig, domains: list[str], certname: str
+               ) -> tuple[bool, Optional[storage.RenewableCert]]:
     """Finds an existing certificate object given domains and/or a certificate name.
 
     :param config: Configuration object
@@ -372,8 +370,8 @@ def _find_cert(config: configuration.NamespaceConfig, domains: List[str], certna
 
 
 def _find_lineage_for_domains_and_certname(
-        config: configuration.NamespaceConfig, domains: List[str],
-        certname: str) -> Tuple[Optional[str], Optional[storage.RenewableCert]]:
+        config: configuration.NamespaceConfig, domains: list[str],
+        certname: str) -> tuple[Optional[str], Optional[storage.RenewableCert]]:
     """Find appropriate lineage based on given domains and/or certname.
 
     :param config: Configuration object
@@ -417,7 +415,7 @@ def _find_lineage_for_domains_and_certname(
 T = TypeVar("T")
 
 
-def _get_added_removed(after: Iterable[T], before: Iterable[T]) -> Tuple[List[T], List[T]]:
+def _get_added_removed(after: Iterable[T], before: Iterable[T]) -> tuple[list[T], list[T]]:
     """Get lists of items removed from `before`
     and a lists of items added to `after`
     """
@@ -482,7 +480,7 @@ def _ask_user_to_confirm_new_names(config: configuration.NamespaceConfig,
 
 def _find_domains_or_certname(config: configuration.NamespaceConfig,
                               installer: Optional[interfaces.Installer],
-                              question: Optional[str] = None) -> Tuple[List[str], str]:
+                              question: Optional[str] = None) -> tuple[list[str], str]:
     """Retrieve domains and certname from config or user input.
 
     :param config: Configuration object
@@ -543,7 +541,7 @@ def _report_next_steps(config: configuration.NamespaceConfig, installer_err: Opt
                                      being saved (created or renewed).
 
     """
-    steps: List[str] = []
+    steps: list[str] = []
 
     # If the installation or enhancement raised an error, show advice on trying again
     if installer_err:
@@ -696,7 +694,7 @@ def _csr_report_new_cert(config: configuration.NamespaceConfig, cert_path: Optio
 
 
 def _determine_account(config: configuration.NamespaceConfig
-                       ) -> Tuple[account.Account,
+                       ) -> tuple[account.Account,
                                   Optional[acme_client.ClientV2]]:
     """Determine which account to use.
 
@@ -1037,7 +1035,7 @@ def _cert_name_from_config_or_lineage(config: configuration.NamespaceConfig,
 
 
 def _install_cert(config: configuration.NamespaceConfig, le_client: client.Client,
-                  domains: List[str], lineage: Optional[storage.RenewableCert] = None) -> None:
+                  domains: list[str], lineage: Optional[storage.RenewableCert] = None) -> None:
     """Install a cert
 
     :param config: Configuration object
@@ -1469,7 +1467,7 @@ def run(config: configuration.NamespaceConfig,
 
 
 def _csr_get_and_save_cert(config: configuration.NamespaceConfig,
-                           le_client: client.Client) -> Tuple[
+                           le_client: client.Client) -> tuple[
                            Optional[str], Optional[str], Optional[str]]:
     """Obtain a cert using a user-supplied CSR
 
@@ -1823,7 +1821,7 @@ def make_displayer(config: configuration.NamespaceConfig
             devnull.close()
 
 
-def main(cli_args: Optional[List[str]] = None) -> Optional[Union[str, int]]:
+def main(cli_args: Optional[list[str]] = None) -> Optional[Union[str, int]]:
     """Run Certbot.
 
     :param cli_args: command line to Certbot, defaults to ``sys.argv[1:]``
diff --git a/certbot/src/certbot/_internal/plugins/disco.py b/certbot/src/certbot/_internal/plugins/disco.py
index 3c98a7c83..80d839169 100644
--- a/certbot/src/certbot/_internal/plugins/disco.py
+++ b/certbot/src/certbot/_internal/plugins/disco.py
@@ -3,13 +3,10 @@ import logging
 import sys
 from typing import Callable
 from typing import cast
-from typing import Dict
 from typing import Iterable
 from typing import Iterator
-from typing import List
 from typing import Mapping
 from typing import Optional
-from typing import Type
 from typing import Union
 
 from certbot import configuration
@@ -39,7 +36,7 @@ class PluginEntryPoint:
 
     def __init__(self, entry_point: importlib_metadata.EntryPoint) -> None:
         self.name = self.entry_point_to_plugin_name(entry_point)
-        self.plugin_cls: Type[interfaces.Plugin] = entry_point.load()
+        self.plugin_cls: type[interfaces.Plugin] = entry_point.load()
         self.entry_point = entry_point
         self.warning_message: Optional[str] = None
         self._initialized: Optional[interfaces.Plugin] = None
@@ -76,7 +73,7 @@ class PluginEntryPoint:
         """Should this plugin be hidden from UI?"""
         return getattr(self.plugin_cls, "hidden", False)
 
-    def ifaces(self, *ifaces_groups: Iterable[Type]) -> bool:
+    def ifaces(self, *ifaces_groups: Iterable[type]) -> bool:
         """Does plugin implement specified interface groups?"""
         return not ifaces_groups or any(
             all(issubclass(self.plugin_cls, iface)
@@ -182,7 +179,7 @@ class PluginsRegistry(Mapping):
         entry points.
 
         """
-        plugins: Dict[str, PluginEntryPoint] = {}
+        plugins: dict[str, PluginEntryPoint] = {}
         plugin_paths_string = os.getenv('CERTBOT_PLUGIN_PATH')
         plugin_paths = plugin_paths_string.split(':') if plugin_paths_string else []
         # XXX should ensure this only happens once
@@ -204,7 +201,7 @@ class PluginsRegistry(Mapping):
 
     @classmethod
     def _load_entry_point(cls, entry_point: importlib_metadata.EntryPoint,
-                          plugins: Dict[str, PluginEntryPoint]) -> None:
+                          plugins: dict[str, PluginEntryPoint]) -> None:
         plugin_ep = PluginEntryPoint(entry_point)
         if plugin_ep.name in plugins:
             other_ep = plugins[plugin_ep.name]
@@ -230,7 +227,7 @@ class PluginsRegistry(Mapping):
     def __len__(self) -> int:
         return len(self._plugins)
 
-    def init(self, config: configuration.NamespaceConfig) -> List[interfaces.Plugin]:
+    def init(self, config: configuration.NamespaceConfig) -> list[interfaces.Plugin]:
         """Initialize all plugins in the registry."""
         return [plugin_ep.init(config) for plugin_ep
                 in self._plugins.values()]
@@ -244,11 +241,11 @@ class PluginsRegistry(Mapping):
         """Filter plugins based on visibility."""
         return self.filter(lambda plugin_ep: not plugin_ep.hidden)
 
-    def ifaces(self, *ifaces_groups: Iterable[Type]) -> "PluginsRegistry":
+    def ifaces(self, *ifaces_groups: Iterable[type]) -> "PluginsRegistry":
         """Filter plugins based on interfaces."""
         return self.filter(lambda p_ep: p_ep.ifaces(*ifaces_groups))
 
-    def prepare(self) -> List[Union[bool, Error]]:
+    def prepare(self) -> list[Union[bool, Error]]:
         """Prepare all plugins in the registry."""
         return [plugin_ep.prepare() for plugin_ep in self._plugins.values()]
 
diff --git a/certbot/src/certbot/_internal/plugins/manual.py b/certbot/src/certbot/_internal/plugins/manual.py
index 4049984ec..01f924773 100644
--- a/certbot/src/certbot/_internal/plugins/manual.py
+++ b/certbot/src/certbot/_internal/plugins/manual.py
@@ -2,11 +2,7 @@
 import logging
 from typing import Any
 from typing import Callable
-from typing import Dict
 from typing import Iterable
-from typing import List
-from typing import Tuple
-from typing import Type
 
 from acme import challenges
 from certbot import achallenges
@@ -98,7 +94,7 @@ permitted by DNS standards.)
         super().__init__(*args, **kwargs)
         self.reverter = reverter.Reverter(self.config)
         self.reverter.recovery_routine()
-        self.env: Dict[achallenges.AnnotatedChallenge, Dict[str, str]] = {}
+        self.env: dict[achallenges.AnnotatedChallenge, dict[str, str]] = {}
         self.subsequent_dns_challenge = False
         self.subsequent_any_challenge = False
 
@@ -132,7 +128,7 @@ permitted by DNS standards.)
             'the user or by performing the setup manually.')
 
     def auth_hint(self, failed_achalls: Iterable[achallenges.AnnotatedChallenge]) -> str:
-        def has_chall(cls: Type[challenges.Challenge]) -> bool:
+        def has_chall(cls: type[challenges.Challenge]) -> bool:
             return any(isinstance(achall.chall, cls) for achall in failed_achalls)
 
         has_dns = has_chall(challenges.DNS01)
@@ -167,12 +163,12 @@ permitted by DNS standards.)
                 )
             )
 
-    def get_chall_pref(self, domain: str) -> Iterable[Type[challenges.Challenge]]:
+    def get_chall_pref(self, domain: str) -> Iterable[type[challenges.Challenge]]:
         # pylint: disable=unused-argument,missing-function-docstring
         return [challenges.HTTP01, challenges.DNS01]
 
-    def perform(self, achalls: List[achallenges.AnnotatedChallenge]
-                ) -> List[challenges.ChallengeResponse]:  # pylint: disable=missing-function-docstring
+    def perform(self, achalls: list[achallenges.AnnotatedChallenge]
+                ) -> list[challenges.ChallengeResponse]:  # pylint: disable=missing-function-docstring
         responses = []
         last_dns_achall = 0
         for i, achall in enumerate(achalls):
@@ -187,7 +183,7 @@ permitted by DNS standards.)
         return responses
 
     def _perform_achall_with_script(self, achall: achallenges.AnnotatedChallenge,
-                                    achalls: List[achallenges.AnnotatedChallenge]) -> None:
+                                    achalls: list[achallenges.AnnotatedChallenge]) -> None:
         env = {
             "CERTBOT_DOMAIN": achall.domain,
             "CERTBOT_VALIDATION": achall.validation(achall.account_key),
@@ -245,7 +241,7 @@ permitted by DNS standards.)
                 self._execute_hook('cleanup-hook', achall.domain)
         self.reverter.recovery_routine()
 
-    def _execute_hook(self, hook_name: str, achall_domain: str) -> Tuple[str, str]:
+    def _execute_hook(self, hook_name: str, achall_domain: str) -> tuple[str, str]:
         returncode, err, out = misc.execute_command_status(
             self.option_name(hook_name), self.conf(hook_name),
             env=util.env_no_snap_for_external_calls()
diff --git a/certbot/src/certbot/_internal/plugins/null.py b/certbot/src/certbot/_internal/plugins/null.py
index e79a88bb9..b73cd7b96 100644
--- a/certbot/src/certbot/_internal/plugins/null.py
+++ b/certbot/src/certbot/_internal/plugins/null.py
@@ -1,7 +1,6 @@
 """Null plugin."""
 import logging
 from typing import Callable
-from typing import List
 from typing import Optional
 from typing import Union
 
@@ -29,7 +28,7 @@ class Installer(common.Plugin, interfaces.Installer):
     def more_info(self) -> str:
         return "Installer that doesn't do anything (for testing)."
 
-    def get_all_names(self) -> List[str]:
+    def get_all_names(self) -> list[str]:
         return []
 
     def deploy_cert(self, domain: str, cert_path: str, key_path: str,
@@ -37,10 +36,10 @@ class Installer(common.Plugin, interfaces.Installer):
         pass  # pragma: no cover
 
     def enhance(self, domain: str, enhancement: str,
-                options: Optional[Union[List[str], str]] = None) -> None:
+                options: Optional[Union[list[str], str]] = None) -> None:
         pass  # pragma: no cover
 
-    def supported_enhancements(self) -> List[str]:
+    def supported_enhancements(self) -> list[str]:
         return []
 
     def save(self, title: Optional[str] = None, temporary: bool = False) -> None:
diff --git a/certbot/src/certbot/_internal/plugins/selection.py b/certbot/src/certbot/_internal/plugins/selection.py
index 4e1bdf7ea..1606634a6 100644
--- a/certbot/src/certbot/_internal/plugins/selection.py
+++ b/certbot/src/certbot/_internal/plugins/selection.py
@@ -3,10 +3,7 @@
 import logging
 from typing import cast
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
-from typing import Type
 from typing import TypeVar
 
 from certbot import configuration
@@ -82,7 +79,7 @@ P = TypeVar('P', bound=interfaces.Plugin)
 
 def pick_plugin(config: configuration.NamespaceConfig, default: Optional[str],
                 plugins: disco.PluginsRegistry, question: str,
-                ifaces: Iterable[Type]) -> Optional[P]:
+                ifaces: Iterable[type]) -> Optional[P]:
     """Pick plugin.
 
     :param certbot.configuration.NamespaceConfig config: Configuration
@@ -136,7 +133,7 @@ def pick_plugin(config: configuration.NamespaceConfig, default: Optional[str],
         return None
 
 
-def choose_plugin(prepared: List[disco.PluginEntryPoint],
+def choose_plugin(prepared: list[disco.PluginEntryPoint],
                   question: str) -> Optional[disco.PluginEntryPoint]:
     """Allow the user to choose their plugin.
 
@@ -193,7 +190,7 @@ def record_chosen_plugins(config: configuration.NamespaceConfig, plugins: disco.
 
 def choose_configurator_plugins(config: configuration.NamespaceConfig,
                                 plugins: disco.PluginsRegistry,
-                                verb: str) -> Tuple[Optional[interfaces.Installer],
+                                verb: str) -> tuple[Optional[interfaces.Installer],
                                                     Optional[interfaces.Authenticator]]:
     """
     Figure out which configurator we're going to use, modifies
@@ -290,7 +287,7 @@ def set_configurator(previously: Optional[str], now: Optional[str]) -> Optional[
 
 
 def cli_plugin_requests(config: configuration.NamespaceConfig
-                        ) -> Tuple[Optional[str], Optional[str]]:
+                        ) -> tuple[Optional[str], Optional[str]]:
     """
     Figure out which plugins the user requested with CLI and config options
 
diff --git a/certbot/src/certbot/_internal/plugins/standalone.py b/certbot/src/certbot/_internal/plugins/standalone.py
index 5173a0cb3..9546df0a0 100644
--- a/certbot/src/certbot/_internal/plugins/standalone.py
+++ b/certbot/src/certbot/_internal/plugins/standalone.py
@@ -4,13 +4,7 @@ import errno
 import logging
 from typing import Any
 from typing import Callable
-from typing import DefaultDict
-from typing import Dict
 from typing import Iterable
-from typing import List
-from typing import Set
-from typing import Tuple
-from typing import Type
 from typing import TYPE_CHECKING
 
 from acme import challenges
@@ -24,9 +18,9 @@ from certbot.plugins import common
 logger = logging.getLogger(__name__)
 
 if TYPE_CHECKING:
-    ServedType = DefaultDict[
+    ServedType = collections.defaultdict[
         acme_standalone.BaseDualNetworkedServers,
-        Set[achallenges.AnnotatedChallenge]
+        set[achallenges.AnnotatedChallenge]
     ]
 
 
@@ -34,12 +28,12 @@ class ServerManager:
     """Manager for HTTP-01 standalone server instances."""
 
     def __init__(self,
-                 http_01_resources: Set[acme_standalone.HTTP01RequestHandler.HTTP01Resource]
+                 http_01_resources: set[acme_standalone.HTTP01RequestHandler.HTTP01Resource]
                  ) -> None:
-        self._instances: Dict[int, acme_standalone.HTTP01DualNetworkedServers] = {}
+        self._instances: dict[int, acme_standalone.HTTP01DualNetworkedServers] = {}
         self.http_01_resources = http_01_resources
 
-    def run(self, port: int, challenge_type: Type[challenges.Challenge],
+    def run(self, port: int, challenge_type: type[challenges.Challenge],
             listenaddr: str = "") -> acme_standalone.HTTP01DualNetworkedServers:
         """Run ACME server on specified ``port``.
 
@@ -87,7 +81,7 @@ class ServerManager:
         instance.shutdown_and_server_close()
         del self._instances[port]
 
-    def running(self) -> Dict[int, acme_standalone.HTTP01DualNetworkedServers]:
+    def running(self) -> dict[int, acme_standalone.HTTP01DualNetworkedServers]:
         """Return all running instances.
 
         Once the server is stopped using `stop`, it will not be
@@ -122,7 +116,7 @@ running. HTTP challenge only (wildcards not supported)."""
         # values, main thread writes). Due to the nature of CPython's
         # GIL, the operations are safe, c.f.
         # https://docs.python.org/2/faq/library.html#what-kinds-of-global-value-mutation-are-thread-safe
-        self.http_01_resources: Set[acme_standalone.HTTP01RequestHandler.HTTP01Resource] = set()
+        self.http_01_resources: set[acme_standalone.HTTP01RequestHandler.HTTP01Resource] = set()
 
         self.servers = ServerManager(self.http_01_resources)
 
@@ -139,12 +133,12 @@ running. HTTP challenge only (wildcards not supported)."""
     def prepare(self) -> None:  # pylint: disable=missing-function-docstring
         pass
 
-    def get_chall_pref(self, domain: str) -> Iterable[Type[challenges.Challenge]]:
+    def get_chall_pref(self, domain: str) -> Iterable[type[challenges.Challenge]]:
         # pylint: disable=unused-argument,missing-function-docstring
         return [challenges.HTTP01]
 
     def perform(self, achalls: Iterable[achallenges.AnnotatedChallenge]
-                ) -> List[challenges.ChallengeResponse]:  # pylint: disable=missing-function-docstring
+                ) -> list[challenges.ChallengeResponse]:  # pylint: disable=missing-function-docstring
         return [self._try_perform_single(achall) for achall in achalls]
 
     def _try_perform_single(self,
@@ -162,7 +156,7 @@ running. HTTP challenge only (wildcards not supported)."""
         return response
 
     def _perform_http_01(self, achall: achallenges.AnnotatedChallenge
-                         ) -> Tuple[acme_standalone.HTTP01DualNetworkedServers,
+                         ) -> tuple[acme_standalone.HTTP01DualNetworkedServers,
                                     challenges.ChallengeResponse]:
         port = self.config.http01_port
         addr = self.config.http01_address
@@ -183,7 +177,7 @@ running. HTTP challenge only (wildcards not supported)."""
             if not self.served[servers]:
                 self.servers.stop(port)
 
-    def auth_hint(self, failed_achalls: List[achallenges.AnnotatedChallenge]) -> str:
+    def auth_hint(self, failed_achalls: list[achallenges.AnnotatedChallenge]) -> str:
         port, addr = self.config.http01_port, self.config.http01_address
         neat_addr = f"{addr}:{port}" if addr else f"port {port}"
         return ("The Certificate Authority failed to download the challenge files from "
diff --git a/certbot/src/certbot/_internal/plugins/webroot.py b/certbot/src/certbot/_internal/plugins/webroot.py
index d7ae89d00..f629931c3 100644
--- a/certbot/src/certbot/_internal/plugins/webroot.py
+++ b/certbot/src/certbot/_internal/plugins/webroot.py
@@ -5,14 +5,9 @@ import json
 import logging
 from typing import Any
 from typing import Callable
-from typing import DefaultDict
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Optional
 from typing import Sequence
-from typing import Set
-from typing import Type
 from typing import Union
 
 from acme import challenges
@@ -88,27 +83,29 @@ to serve all files under specified web root ({0})."""
                  "file, it needs to be on a single line, like: webroot-map = "
                  '{"example.com":"/var/www"}.')
 
-    def auth_hint(self, failed_achalls: List[AnnotatedChallenge]) -> str:  # pragma: no cover
+    def auth_hint(self, failed_achalls: list[AnnotatedChallenge]) -> str:  # pragma: no cover
         return ("The Certificate Authority failed to download the temporary challenge files "
                 "created by Certbot. Ensure that the listed domains serve their content from "
                 "the provided --webroot-path/-w and that files created there can be downloaded "
                 "from the internet.")
 
-    def get_chall_pref(self, domain: str) -> Iterable[Type[challenges.Challenge]]:
+    def get_chall_pref(self, domain: str) -> Iterable[type[challenges.Challenge]]:
         # pylint: disable=unused-argument,missing-function-docstring
         return [challenges.HTTP01]
 
     def __init__(self, *args: Any, **kwargs: Any) -> None:
         super().__init__(*args, **kwargs)
-        self.full_roots: Dict[str, str] = {}
-        self.performed: DefaultDict[str, Set[AnnotatedChallenge]] = collections.defaultdict(set)
+        self.full_roots: dict[str, str] = {}
+        self.performed: collections.defaultdict[str, set[AnnotatedChallenge]] = (
+            collections.defaultdict(set)
+        )
         # stack of dirs successfully created by this authenticator
-        self._created_dirs: List[str] = []
+        self._created_dirs: list[str] = []
 
     def prepare(self) -> None:  # pylint: disable=missing-function-docstring
         pass
 
-    def perform(self, achalls: List[AnnotatedChallenge]) -> List[challenges.ChallengeResponse]:  # pylint: disable=missing-function-docstring
+    def perform(self, achalls: list[AnnotatedChallenge]) -> list[challenges.ChallengeResponse]:  # pylint: disable=missing-function-docstring
         self._set_webroots(achalls)
 
         self._create_challenge_dirs()
@@ -137,7 +134,7 @@ to serve all files under specified web root ({0})."""
                     known_webroots.insert(0, new_webroot)
                     self.conf("map")[achall.domain] = new_webroot
 
-    def _prompt_for_webroot(self, domain: str, known_webroots: List[str]) -> Optional[str]:
+    def _prompt_for_webroot(self, domain: str, known_webroots: list[str]) -> Optional[str]:
         webroot = None
 
         while webroot is None:
@@ -153,7 +150,7 @@ to serve all files under specified web root ({0})."""
         return webroot
 
     def _prompt_with_webroot_list(self, domain: str,
-                                  known_webroots: List[str]) -> Optional[str]:
+                                  known_webroots: list[str]) -> Optional[str]:
         path_flag = "--" + self.option_name("path")
 
         while True:
@@ -253,7 +250,7 @@ to serve all files under specified web root ({0})."""
         self.performed[root_path].add(achall)
         return response
 
-    def cleanup(self, achalls: List[AnnotatedChallenge]) -> None:  # pylint: disable=missing-function-docstring
+    def cleanup(self, achalls: list[AnnotatedChallenge]) -> None:  # pylint: disable=missing-function-docstring
         for achall in achalls:
             root_path = self.full_roots.get(achall.domain, None)
             if root_path is not None:
@@ -274,7 +271,7 @@ to serve all files under specified web root ({0})."""
                             logger.info("Not cleaning up the web.config file in %s "
                                         "because it is not generated by Certbot.", root_path)
 
-        not_removed: List[str] = []
+        not_removed: list[str] = []
         while self._created_dirs:
             path = self._created_dirs.pop()
             try:
diff --git a/certbot/src/certbot/_internal/renewal.py b/certbot/src/certbot/_internal/renewal.py
index ad0bf52a5..6fe02679b 100644
--- a/certbot/src/certbot/_internal/renewal.py
+++ b/certbot/src/certbot/_internal/renewal.py
@@ -9,9 +9,7 @@ import sys
 import time
 import traceback
 from typing import Any
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Mapping
 from typing import Optional
 from typing import Union
@@ -70,7 +68,7 @@ class AriClientPool:
     def __init__(self, cli_config: configuration.NamespaceConfig):
         self._verify_ssl = not cli_config.no_verify_ssl
         self._user_agent = client.determine_user_agent(cli_config)
-        self._pool: Dict[str, acme_client.ClientV2] = {}
+        self._pool: dict[str, acme_client.ClientV2] = {}
 
     def get(self, server: str) -> acme_client.ClientV2:
         """
@@ -196,7 +194,7 @@ def _restore_plugin_configs(config: configuration.NamespaceConfig,
     #      longer defined, stored copies of that parameter will be
     #      deserialized as strings by this logic even if they were
     #      originally meant to be some other type.
-    plugin_prefixes: List[str] = []
+    plugin_prefixes: list[str] = []
     if renewalparams["authenticator"] == "webroot":
         _restore_webroot_config(config, renewalparams)
     else:
@@ -245,7 +243,7 @@ def restore_required_config_elements(config: configuration.NamespaceConfig,
         setattr(config, key, value)
 
 
-def _remove_deprecated_config_elements(renewalparams: Mapping[str, Any]) -> Dict[str, Any]:
+def _remove_deprecated_config_elements(renewalparams: Mapping[str, Any]) -> dict[str, Any]:
     """Removes deprecated config options from the parsed renewalparams.
 
     :param dict renewalparams: list of parsed renewalparams
@@ -258,7 +256,7 @@ def _remove_deprecated_config_elements(renewalparams: Mapping[str, Any]) -> Dict
         if option_name not in cli.DEPRECATED_OPTIONS}
 
 
-def _restore_pref_challs(unused_name: str, value: Union[List[str], str]) -> List[str]:
+def _restore_pref_challs(unused_name: str, value: Union[list[str], str]) -> list[str]:
     """Restores preferred challenges from a renewal config file.
 
     If value is a `str`, it should be a single challenge type.
@@ -525,7 +523,7 @@ def _avoid_reuse_key_conflicts(config: configuration.NamespaceConfig,
                 "add --new-key.")
 
 
-def renew_cert(config: configuration.NamespaceConfig, domains: Optional[List[str]],
+def renew_cert(config: configuration.NamespaceConfig, domains: Optional[list[str]],
                le_client: client.Client, lineage: storage.RenewableCert) -> None:
     """Renew a certificate lineage."""
     renewal_params = lineage.configuration["renewalparams"]
@@ -560,9 +558,9 @@ def report(msgs: Iterable[str], category: str) -> str:
     return "  " + "\n  ".join(lines)
 
 
-def _renew_describe_results(config: configuration.NamespaceConfig, renew_successes: List[str],
-                            renew_failures: List[str], renew_skipped: List[str],
-                            parse_failures: List[str]) -> None:
+def _renew_describe_results(config: configuration.NamespaceConfig, renew_successes: list[str],
+                            renew_failures: list[str], renew_skipped: list[str],
+                            parse_failures: list[str]) -> None:
     """
     Print a report to the terminal about the results of the renewal process.
 
diff --git a/certbot/src/certbot/_internal/snap_config.py b/certbot/src/certbot/_internal/snap_config.py
index 855c5662f..072961dde 100644
--- a/certbot/src/certbot/_internal/snap_config.py
+++ b/certbot/src/certbot/_internal/snap_config.py
@@ -3,9 +3,7 @@ from __future__ import annotations
 import logging
 import socket
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
 from typing import Union
 
 from requests import PreparedRequest, Session
@@ -39,7 +37,7 @@ CURRENT_PYTHON_VERSION_STRING = 'python3.12'
 LOGGER = logging.getLogger(__name__)
 
 
-def prepare_env(cli_args: List[str]) -> List[str]:
+def prepare_env(cli_args: list[str]) -> list[str]:
     """
     Prepare runtime environment for a certbot execution in snap.
     :param list cli_args: List of command line arguments
@@ -142,7 +140,7 @@ class _SnapdAdapter(HTTPAdapter):
     def get_connection_with_tls_context(self, request: PreparedRequest,
                                         verify: bool | str | None,
                                         proxies: Optional[Iterable[str]] = None,
-                                        cert: Optional[Union[str, Tuple[str,str]]] = None
+                                        cert: Optional[Union[str, tuple[str,str]]] = None
                                         ) -> _SnapdConnectionPool:
         """Required method for creating a new connection pool. Simply return our
         shim that forces a UNIX socket connection to snapd."""
diff --git a/certbot/src/certbot/_internal/storage.py b/certbot/src/certbot/_internal/storage.py
index 111c10362..ab6a36dea 100644
--- a/certbot/src/certbot/_internal/storage.py
+++ b/certbot/src/certbot/_internal/storage.py
@@ -8,12 +8,9 @@ import shutil
 import stat
 from typing import Any
 from typing import cast
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Mapping
 from typing import Optional
-from typing import Tuple
 from typing import Union
 
 import configobj
@@ -47,7 +44,7 @@ BASE_PRIVKEY_MODE = 0o600
 # pylint: disable=too-many-lines
 
 
-def renewal_conf_files(config: configuration.NamespaceConfig) -> List[str]:
+def renewal_conf_files(config: configuration.NamespaceConfig) -> list[str]:
     """Build a list of all renewal configuration files.
 
     :param configuration.NamespaceConfig config: Configuration object
@@ -266,7 +263,7 @@ def _relevant(namespaces: Iterable[str], option: str) -> bool:
             any(option.startswith(namespace) for namespace in namespaces))
 
 
-def relevant_values(config: configuration.NamespaceConfig) -> Dict[str, Any]:
+def relevant_values(config: configuration.NamespaceConfig) -> dict[str, Any]:
     """Return a new dict containing only items relevant for renewal.
 
     :param .NamespaceConfig config: parsed command line
@@ -656,7 +653,7 @@ class RenewableCert(interfaces.RenewableCert):
     #       happen as a result of random tampering by a sysadmin, or
     #       filesystem errors, or crashes.)
 
-    def _previous_symlinks(self) -> List[Tuple[str, str]]:
+    def _previous_symlinks(self) -> list[tuple[str, str]]:
         """Returns the kind and path of all symlinks used in recovery.
 
         :returns: list of (kind, symlink) tuples
@@ -760,7 +757,7 @@ class RenewableCert(interfaces.RenewableCert):
         where = os.path.dirname(link)
         return os.path.join(where, "{0}{1}.pem".format(kind, version))
 
-    def available_versions(self, kind: str) -> List[int]:
+    def available_versions(self, kind: str) -> list[int]:
         """Which alternative versions of the specified kind of item exist?
 
         The archive directory where the current version is stored is
@@ -849,7 +846,7 @@ class RenewableCert(interfaces.RenewableCert):
         :rtype: bool
 
         """
-        all_versions: List[int] = []
+        all_versions: list[int] = []
         for item in ALL_FOUR:
             version = self.current_version(item)
             if version is None:
@@ -906,7 +903,7 @@ class RenewableCert(interfaces.RenewableCert):
             for _, link in previous_links:
                 os.unlink(link)
 
-    def names(self) -> List[str]:
+    def names(self) -> list[str]:
         """What are the subject names of this certificate?
 
         :returns: the subject names
diff --git a/certbot/src/certbot/_internal/tests/cli_test.py b/certbot/src/certbot/_internal/tests/cli_test.py
index f55ae65be..5cc7ea332 100644
--- a/certbot/src/certbot/_internal/tests/cli_test.py
+++ b/certbot/src/certbot/_internal/tests/cli_test.py
@@ -4,7 +4,7 @@ import copy
 import io
 import sys
 import tempfile
-from typing import Any, List
+from typing import Any
 import unittest
 from unittest import mock
 
@@ -85,17 +85,17 @@ class ParseTest(unittest.TestCase):
     '''Test the cli args entrypoint'''
 
     @staticmethod
-    def _unmocked_parse(args: List[str]) -> NamespaceConfig:
+    def _unmocked_parse(args: list[str]) -> NamespaceConfig:
         """Get result of cli.prepare_and_parse_args."""
         return cli.prepare_and_parse_args(PLUGINS, args)
 
     @staticmethod
-    def parse(args: List[str]) -> NamespaceConfig:
+    def parse(args: list[str]) -> NamespaceConfig:
         """Mocks certbot._internal.display.obj.get_display and calls _unmocked_parse."""
         with test_util.patch_display_util():
             return ParseTest._unmocked_parse(args)
 
-    def _help_output(self, args: List[str]):
+    def _help_output(self, args: list[str]):
         "Run a command, and return the output string for scrutiny"
 
         output = io.StringIO()
diff --git a/certbot/src/certbot/_internal/tests/display/completer_test.py b/certbot/src/certbot/_internal/tests/display/completer_test.py
index ef013d520..0a5353f26 100644
--- a/certbot/src/certbot/_internal/tests/display/completer_test.py
+++ b/certbot/src/certbot/_internal/tests/display/completer_test.py
@@ -2,7 +2,6 @@
 from importlib import reload as reload_module
 import string
 import sys
-from typing import List
 import unittest
 from unittest import mock
 
@@ -30,7 +29,7 @@ class CompleterTest(test_util.TempDirTestCase):
         if self.tempdir[-1] != os.sep:
             self.tempdir += os.sep
 
-        self.paths: List[str] = []
+        self.paths: list[str] = []
         # create some files and directories in temp_dir
         for c in string.ascii_lowercase:
             path = os.path.join(self.tempdir, c)
diff --git a/certbot/src/certbot/_internal/tests/error_handler_test.py b/certbot/src/certbot/_internal/tests/error_handler_test.py
index 30bd90150..be001cf87 100644
--- a/certbot/src/certbot/_internal/tests/error_handler_test.py
+++ b/certbot/src/certbot/_internal/tests/error_handler_test.py
@@ -3,7 +3,6 @@ import contextlib
 import signal
 import sys
 from typing import Callable
-from typing import Dict
 from typing import Union
 import unittest
 from unittest import mock
@@ -28,7 +27,7 @@ def set_signals(sig_handler_dict):
 def signal_receiver(signums):
     """Context manager to catch signals"""
     signals = []
-    prev_handlers: Dict[int, Union[int, None, Callable]] = get_signals(signums)
+    prev_handlers: dict[int, Union[int, None, Callable]] = get_signals(signums)
     set_signals({s: lambda s, _: signals.append(s) for s in signums})
     yield signals
     set_signals(prev_handlers)
diff --git a/certbot/src/certbot/_internal/tests/hook_test.py b/certbot/src/certbot/_internal/tests/hook_test.py
index 268b5a84e..305b306f6 100644
--- a/certbot/src/certbot/_internal/tests/hook_test.py
+++ b/certbot/src/certbot/_internal/tests/hook_test.py
@@ -11,7 +11,6 @@ from certbot import util
 from certbot.compat import filesystem
 from certbot.compat import os
 from certbot.tests import util as test_util
-from typing import List
 
 
 def pyver_lt(major: int, minor: int):
@@ -292,7 +291,7 @@ class RunSavedPostHooksTest(HookTest):
 
     def setUp(self):
         super().setUp()
-        self.eventually: List[str] = []
+        self.eventually: list[str] = []
 
     def test_empty(self):
         assert not self._call_with_mock_execute_and_eventually([], []).called
diff --git a/certbot/src/certbot/_internal/tests/main_test.py b/certbot/src/certbot/_internal/tests/main_test.py
index 32146ce59..640ec01c3 100644
--- a/certbot/src/certbot/_internal/tests/main_test.py
+++ b/certbot/src/certbot/_internal/tests/main_test.py
@@ -11,7 +11,6 @@ import shutil
 import sys
 import tempfile
 import traceback
-from typing import List
 import unittest
 from unittest import mock
 
@@ -1237,7 +1236,7 @@ class MainTest(test_util.ConfigTestCase):
     @mock.patch('certbot._internal.main.plugins_disco')
     @mock.patch('certbot._internal.main.cli.HelpfulArgumentParser.determine_help_topics')
     def test_plugins_no_args(self, _det, mock_disco):
-        ifaces: List[interfaces.Plugin] = []
+        ifaces: list[interfaces.Plugin] = []
         plugins = mock_disco.PluginsRegistry.find_all()
 
         stdout = io.StringIO()
@@ -1252,7 +1251,7 @@ class MainTest(test_util.ConfigTestCase):
     @mock.patch('certbot._internal.main.plugins_disco')
     @mock.patch('certbot._internal.main.cli.HelpfulArgumentParser.determine_help_topics')
     def test_plugins_no_args_unprivileged(self, _det, mock_disco):
-        ifaces: List[interfaces.Plugin] = []
+        ifaces: list[interfaces.Plugin] = []
         plugins = mock_disco.PluginsRegistry.find_all()
 
         def throw_error(directory, mode, strict):
@@ -1274,7 +1273,7 @@ class MainTest(test_util.ConfigTestCase):
     @mock.patch('certbot._internal.main.plugins_disco')
     @mock.patch('certbot._internal.main.cli.HelpfulArgumentParser.determine_help_topics')
     def test_plugins_init(self, _det, mock_disco):
-        ifaces: List[interfaces.Plugin] = []
+        ifaces: list[interfaces.Plugin] = []
         plugins = mock_disco.PluginsRegistry.find_all()
 
         stdout = io.StringIO()
@@ -1290,7 +1289,7 @@ class MainTest(test_util.ConfigTestCase):
     @mock.patch('certbot._internal.main.plugins_disco')
     @mock.patch('certbot._internal.main.cli.HelpfulArgumentParser.determine_help_topics')
     def test_plugins_prepare(self, _det, mock_disco):
-        ifaces: List[interfaces.Plugin] = []
+        ifaces: list[interfaces.Plugin] = []
         plugins = mock_disco.PluginsRegistry.find_all()
 
         stdout = io.StringIO()
diff --git a/certbot/src/certbot/_internal/tests/plugins/disco_test.py b/certbot/src/certbot/_internal/tests/plugins/disco_test.py
index 9b4903f8b..2bef8cf07 100644
--- a/certbot/src/certbot/_internal/tests/plugins/disco_test.py
+++ b/certbot/src/certbot/_internal/tests/plugins/disco_test.py
@@ -2,7 +2,6 @@
 import functools
 import string
 import sys
-from typing import List
 import unittest
 from unittest import mock
 
@@ -264,7 +263,7 @@ class PluginsRegistryTest(unittest.TestCase):
         self.plugin_ep.prepare.assert_called_once_with()
 
     def test_prepare_order(self):
-        order: List[str] = []
+        order: list[str] = []
         plugins = {
             c: mock.MagicMock(prepare=functools.partial(order.append, c))
             for c in string.ascii_letters
diff --git a/certbot/src/certbot/_internal/tests/plugins/selection_test.py b/certbot/src/certbot/_internal/tests/plugins/selection_test.py
index cf934913c..3a7e12926 100644
--- a/certbot/src/certbot/_internal/tests/plugins/selection_test.py
+++ b/certbot/src/certbot/_internal/tests/plugins/selection_test.py
@@ -1,6 +1,5 @@
 """Tests for letsencrypt.plugins.selection"""
 import sys
-from typing import List
 import unittest
 from unittest import mock
 
@@ -50,7 +49,7 @@ class PickPluginTest(unittest.TestCase):
         self.default = None
         self.reg = mock.MagicMock()
         self.question = "Question?"
-        self.ifaces: List[interfaces.Plugin] = []
+        self.ifaces: list[interfaces.Plugin] = []
 
     def _call(self):
         from certbot._internal.plugins.selection import pick_plugin
diff --git a/certbot/src/certbot/_internal/tests/plugins/standalone_test.py b/certbot/src/certbot/_internal/tests/plugins/standalone_test.py
index c51f0cba0..73a63ae39 100644
--- a/certbot/src/certbot/_internal/tests/plugins/standalone_test.py
+++ b/certbot/src/certbot/_internal/tests/plugins/standalone_test.py
@@ -2,7 +2,6 @@
 import errno
 import socket
 import sys
-from typing import Set
 import unittest
 from unittest import mock
 
@@ -22,7 +21,7 @@ class ServerManagerTest(unittest.TestCase):
 
     def setUp(self):
         from certbot._internal.plugins.standalone import ServerManager
-        self.http_01_resources: Set[acme_standalone.HTTP01RequestHandler.HTTP01Resource] = {}
+        self.http_01_resources: set[acme_standalone.HTTP01RequestHandler.HTTP01Resource] = {}
         self.mgr = ServerManager(self.http_01_resources)
 
     def test_init(self):