From 4031d3c3890cc89e14299cc7d8584889a3b48ed0 Mon Sep 17 00:00:00 2001
From: Muneeb Sheikh <muneikh@gmail.com>
Date: Sun, 11 Oct 2026 13:23:35 -0400
Subject: [PATCH] Clean up rewrite files when output close fails

---
 src/dotenv/main.py | 13 ++++++-------
 tests/test_main.py | 36 ++++++++++++++++++++++++++++++++++++
 2 files changed, 42 insertions(+), 7 deletions(-)

diff --git a/src/dotenv/main.py b/src/dotenv/main.py
index 5faa7f0e..362a884a 100644
--- a/src/dotenv/main.py
+++ b/src/dotenv/main.py
@@ -197,15 +197,14 @@ def rewrite(
         err.filename = os.fspath(path)
         raise
 
-    with temp_file as dest:
-        dest_path = pathlib.Path(dest.name)
-        error = None
-
-        try:
+    dest_path = pathlib.Path(temp_file.name)
+    error = None
+    try:
+        with temp_file as dest:
             with source:
                 yield (source, dest)
-        except BaseException as err:
-            error = err
+    except BaseException as err:
+        error = err
 
     if error is None:
         try:
diff --git a/tests/test_main.py b/tests/test_main.py
index 930ab171..58c3c451 100644
--- a/tests/test_main.py
+++ b/tests/test_main.py
@@ -948,3 +948,39 @@ def test_dotenv_values_empty_value_with_inline_comment(string, expected):
     result = dotenv.dotenv_values(stream=io.StringIO(string))
 
     assert result == expected
+
+
+@pytest.mark.parametrize("operation", [dotenv.set_key, dotenv.unset_key])
+def test_rewrite_close_failure_leaves_no_temp_file(dotenv_path, operation):
+    dotenv_path.write_text("a=original\n")
+    real_temp_file = dotenv.main.tempfile.NamedTemporaryFile
+    close_error = OSError("flush failed")
+    handles = []
+
+    class FailingClose:
+        def __init__(self, *args, **kwargs):
+            self.file = real_temp_file(*args, **kwargs)
+            handles.append(self.file)
+
+        def __enter__(self):
+            return self.file.__enter__()
+
+        @property
+        def name(self):
+            return self.file.name
+
+        def __exit__(self, *args):
+            self.file.__exit__(*args)
+            raise close_error
+
+    with mock.patch("dotenv.main.tempfile.NamedTemporaryFile", FailingClose):
+        with pytest.raises(OSError) as excinfo:
+            if operation is dotenv.set_key:
+                operation(dotenv_path, "a", "replacement")
+            else:
+                operation(dotenv_path, "a")
+
+    assert excinfo.value is close_error
+    assert all(handle.closed for handle in handles)
+    assert dotenv_path.read_text() == "a=original\n"
+    assert list(dotenv_path.parent.glob(".tmp_*")) == []