diff --git a/mypy.ini b/mypy.ini
index 57e19efa9e..c1d01a42c3 100644
--- a/mypy.ini
+++ b/mypy.ini
@@ -58,7 +58,7 @@ ignore_missing_imports = True
 
 #  - wheel: does not intend on exposing a programmatic API https://github.com/pypa/wheel/pull/610#issuecomment-2081687671
 [mypy-wheel.*]
-ignore_missing_imports = True
+follow_untyped_imports = True
 # - The following are not marked as py.typed:
 #  - jaraco: Since mypy 1.12, the root name of the untyped namespace package gets called-out too
 #  - jaraco.develop: https://github.com/jaraco/jaraco.develop/issues/22
@@ -66,8 +66,8 @@ ignore_missing_imports = True
 #  - jaraco.packaging: https://github.com/jaraco/jaraco.packaging/issues/20
 #  - jaraco.path: https://github.com/jaraco/jaraco.path/issues/2
 #  - jaraco.text: https://github.com/jaraco/jaraco.text/issues/17
-[mypy-jaraco,jaraco.develop,jaraco.envs,jaraco.packaging.*,jaraco.path,jaraco.text]
-ignore_missing_imports = True
+[mypy-jaraco,jaraco.develop.*,jaraco.envs,jaraco.packaging.*,jaraco.path,jaraco.text]
+follow_untyped_imports = True
 
 # Even when excluding a module, import issues can show up due to following import
 # https://github.com/python/mypy/issues/11936#issuecomment-1466764006
diff --git a/pyproject.toml b/pyproject.toml
index a19d4ac164..48df917af8 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -44,7 +44,7 @@ test = [
 	"packaging>=24.2",
 	"jaraco.envs>=2.2",
 	"pytest-xdist>=3", # Dropped dependency on pytest-fork and py
-	"jaraco.path>=3.2.0",
+	"jaraco.path>=3.7.2", # Typing fixes
 	"build[virtualenv]>=1.0.3",
 	"filelock>=3.4.0",
 	"ini2toml[lite]>=0.14",
@@ -135,7 +135,7 @@ type = [
 	# pin mypy version so a new version doesn't suddenly cause the CI to fail,
 	# until types-setuptools is removed from typeshed.
 	# For help with static-typing issues, or mypy update, ping @Avasam
-	"mypy>=1.12,<1.14",
+	"mypy==1.14.*",
 	# Typing fixes in version newer than we require at runtime
 	"importlib_metadata>=7.0.2; python_version < '3.10'",
 	# Imported unconditionally in tools/finalize.py
diff --git a/setuptools/tests/test_build_ext.py b/setuptools/tests/test_build_ext.py
index 88318b26c5..d107a272e1 100644
--- a/setuptools/tests/test_build_ext.py
+++ b/setuptools/tests/test_build_ext.py
@@ -179,11 +179,11 @@ def C(file):
 
 class TestBuildExtInplace:
     def get_build_ext_cmd(self, optional: bool, **opts) -> build_ext:
-        files = {
+        files: dict[str, str | dict[str, dict[str, str]]] = {
             "eggs.c": "#include missingheader.h\n",
             ".build": {"lib": {}, "tmp": {}},
         }
-        path.build(files)  # jaraco/path#232
+        path.build(files)
         extension = Extension('spam.eggs', ['eggs.c'], optional=optional)
         dist = Distribution(dict(ext_modules=[extension]))
         dist.script_name = 'setup.py'
diff --git a/setuptools/tests/test_core_metadata.py b/setuptools/tests/test_core_metadata.py
index cf0bb32e9f..b67373bc37 100644
--- a/setuptools/tests/test_core_metadata.py
+++ b/setuptools/tests/test_core_metadata.py
@@ -5,7 +5,7 @@
 import io
 from email import message_from_string
 from email.generator import Generator
-from email.message import Message
+from email.message import EmailMessage, Message
 from email.parser import Parser
 from email.policy import EmailPolicy
 from pathlib import Path
@@ -416,7 +416,7 @@ def _assert_roundtrip_message(metadata: str) -> None:
     then ensures the metadata generated by setuptools is compatible.
     """
     with io.StringIO(metadata) as buffer:
-        msg = Parser().parse(buffer)
+        msg = Parser(EmailMessage).parse(buffer)
 
     serialization_policy = EmailPolicy(
         utf8=True,