diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index 62c53494..b9d96b1c 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -10,6 +10,7 @@ Changes
 * ENH: Added CLI argument ``-m`` to ``kernprof`` for running a library module as a script; also made it possible for profiling targets to be supplied across multiple ``-p`` flags
 * FIX: Fixed explicit profiling of class methods; added handling for profiling static, bound, and partial methods, ``functools.partial`` objects, (cached) properties, and async generator functions
 * FIX: Fixed namespace bug when running ``kernprof -m`` on certain modules (e.g. ``calendar`` on Python 3.12+).
+* FIX: Fixed ``@contextlib.contextmanager`` bug where the cleanup code (e.g. restoration of ``sys`` attributes) is not run if exceptions occurred inside the context
 
 4.2.0
 ~~~~~
diff --git a/kernprof.py b/kernprof.py
index b8e558cf..52867331 100755
--- a/kernprof.py
+++ b/kernprof.py
@@ -80,7 +80,6 @@ def main():
       --prof-imports        If specified, modules specified to `--prof-mod` will also autoprofile modules that they import. Only works with line_profiler -l, --line-by-line
 """
 import builtins
-import contextlib
 import functools
 import os
 import sys
@@ -224,8 +223,7 @@ def _python_command():
         return sys.executable
 
 
-@contextlib.contextmanager
-def _restore_list(lst):
+class _restore_list:
     """
     Restore a list like `sys.path` after running code which potentially
     modifies it.
@@ -248,9 +246,24 @@ def _restore_list(lst):
     >>> l
     [1, 2, 3]
     """
-    old = lst.copy()
-    yield
-    lst[:] = old
+    def __init__(self, lst):
+        self.lst = lst
+        self.old = None
+
+    def __enter__(self):
+        assert self.old is None
+        self.old = self.lst.copy()
+
+    def __exit__(self, *_, **__):
+        self.old, self.lst[:] = None, self.old
+
+    def __call__(self, func):
+        @functools.wraps(func)
+        def wrapper(*args, **kwargs):
+            with self:
+                return func(*args, **kwargs)
+
+        return wrapper
 
 
 def pre_parse_single_arg_directive(args, flag, sep='--'):
diff --git a/line_profiler/autoprofile/autoprofile.py b/line_profiler/autoprofile/autoprofile.py
index d5894318..5985a84b 100644
--- a/line_profiler/autoprofile/autoprofile.py
+++ b/line_profiler/autoprofile/autoprofile.py
@@ -97,12 +97,21 @@ def run(script_file, ns, prof_mod, profile_imports=False, as_module=False):
         as_module (bool):
             Whether we're running script_file as a module
     """
-    @contextlib.contextmanager
-    def restore_dict(d, target=None):
-        copy = d.copy()
-        yield target
-        d.clear()
-        d.update(copy)
+    class restore_dict:
+        def __init__(self, d, target=None):
+            self.d = d
+            self.target = target
+            self.copy = None
+
+        def __enter__(self):
+            assert self.copy is None
+            self.copy = self.d.copy()
+            return self.target
+
+        def __exit__(self, *_, **__):
+            self.d.clear()
+            self.d.update(self.copy)
+            self.copy = None
 
     if as_module:
         Profiler = AstTreeModuleProfiler
diff --git a/tests/test_kernprof.py b/tests/test_kernprof.py
index cfb7a553..c56dd215 100644
--- a/tests/test_kernprof.py
+++ b/tests/test_kernprof.py
@@ -1,3 +1,4 @@
+import contextlib
 import os
 import re
 import shlex
@@ -8,7 +9,7 @@
 import pytest
 import ubelt as ub
 
-from kernprof import ContextualProfile
+from kernprof import main, ContextualProfile
 
 
 def f(x):
@@ -123,6 +124,59 @@ def main():
     assert ('Function: main' in proc.stdout) == profiled_main
 
 
+@pytest.mark.parametrize('error', [True, False])
+@pytest.mark.parametrize(
+    'args',
+    ['', '-pmymod'],  # Normal execution / auto-profile
+)
+def test_kernprof_sys_restoration(capsys, error, args):
+    """
+    Test that `kernprof.main()` and
+    `line_profiler.autoprofile.autoprofile.run()` (resp.) properly
+    restores `sys.path` (resp. `sys.modules['__main__']`) on the way
+    out.
+
+    Notes
+    -----
+    The test is run in-process.
+    """
+    with contextlib.ExitStack() as stack:
+        enter = stack.enter_context
+        tmpdir = enter(tempfile.TemporaryDirectory())
+        assert tmpdir not in sys.path
+        temp_dpath = ub.Path(tmpdir)
+        (temp_dpath / 'mymod.py').write_text(ub.codeblock(
+            f'''
+            import sys
+
+
+            def main():
+                # Mess up `sys.path`
+                sys.path.append({tmpdir!r})
+                # Output
+                print(1)
+                # Optionally raise an error
+                if {error!r}:
+                    raise Exception
+
+
+            if __name__ == '__main__':
+                main()
+            '''))
+        enter(ub.ChDir(tmpdir))
+        if error:
+            ctx = pytest.raises(BaseException)
+        else:
+            ctx = contextlib.nullcontext()
+        old_main = sys.modules.get('__main__')
+        with ctx:
+            main(['-l', *shlex.split(args), '-m', 'mymod'])
+        out, _ = capsys.readouterr()
+        assert out.startswith('1')
+        assert tmpdir not in sys.path
+        assert sys.modules.get('__main__') is old_main
+
+
 class TestKernprof(unittest.TestCase):
 
     def test_enable_disable(self):
diff --git a/tests/test_line_profiler.py b/tests/test_line_profiler.py
index b2a12028..85860b2a 100644
--- a/tests/test_line_profiler.py
+++ b/tests/test_line_profiler.py
@@ -41,18 +41,28 @@ def strip(s):
     return textwrap.dedent(s).strip('\n')
 
 
-@contextlib.contextmanager
-def check_timings(prof):
+class check_timings:
     """
     Verify that the profiler starts without timing data and ends with
     some.
     """
-    timings = prof.get_stats().timings
-    assert not any(timings.values()), ('Expected no timing entries, '
-                                       f'got {timings!r}')
-    yield prof
-    timings = prof.get_stats().timings
-    assert any(timings.values()), f'Expected timing entries, got {timings!r}'
+    def __init__(self, prof):
+        self.prof = prof
+
+    def __enter__(self):
+        timings = self.timings
+        assert not any(timings.values()), (
+            f'Expected no timing entries, got {timings!r}')
+        return self.prof
+
+    def __exit__(self, *_, **__):
+        timings = self.timings
+        assert any(timings.values()), (
+            f'Expected timing entries, got {timings!r}')
+
+    @property
+    def timings(self):
+        return self.prof.get_stats().timings
 
 
 def test_init():