diff --git a/tests/test_requests.py b/tests/test_requests.py
index ccd8636bad..b724264166 100644
--- a/tests/test_requests.py
+++ b/tests/test_requests.py
@@ -1022,12 +1022,13 @@ def test_form_encoded_post_query_multivalued_element(self, httpbin):
         assert prep.body == "test=foo&test=baz"
 
     def test_different_encodings_dont_break_post(self, httpbin):
-        r = requests.post(
-            httpbin("post"),
-            data={"stuff": json.dumps({"a": 123})},
-            params={"blah": "asdf1234"},
-            files={"file": ("test_requests.py", open(__file__, "rb"))},
-        )
+        with open(__file__, "rb") as f:
+            r = requests.post(
+                httpbin("post"),
+                data={"stuff": json.dumps({"a": 123})},
+                params={"blah": "asdf1234"},
+                files={"file": ("test_requests.py", f)},
+            )
         assert r.status_code == 200
 
     @pytest.mark.parametrize(
@@ -1040,35 +1041,44 @@ def test_different_encodings_dont_break_post(self, httpbin):
         ),
     )
     def test_unicode_multipart_post(self, httpbin, data):
-        r = requests.post(
-            httpbin("post"),
-            data=data,
-            files={"file": ("test_requests.py", open(__file__, "rb"))},
-        )
+        with open(__file__, "rb") as f:
+            r = requests.post(
+                httpbin("post"),
+                data=data,
+                files={"file": ("test_requests.py", f)},
+            )
         assert r.status_code == 200
 
     def test_unicode_multipart_post_fieldnames(self, httpbin):
         filename = os.path.splitext(__file__)[0] + ".py"
-        r = requests.Request(
-            method="POST",
-            url=httpbin("post"),
-            data={b"stuff": "elixr"},
-            files={"file": ("test_requests.py", open(filename, "rb"))},
-        )
-        prep = r.prepare()
+        with open(filename, "rb") as f:
+            r = requests.Request(
+                method="POST",
+                url=httpbin("post"),
+                data={b"stuff": "elixr"},
+                files={"file": ("test_requests.py", f)},
+            )
+            prep = r.prepare()
+
         assert b'name="stuff"' in prep.body
         assert b"name=\"b'stuff'\"" not in prep.body
 
     def test_unicode_method_name(self, httpbin):
-        files = {"file": open(__file__, "rb")}
-        r = requests.request(method="POST", url=httpbin("post"), files=files)
+        with open(__file__, "rb") as f:
+            files = {"file": f}
+            r = requests.request(
+                method="POST",
+                url=httpbin("post"),
+                files=files,
+            )
         assert r.status_code == 200
 
     def test_unicode_method_name_with_request_object(self, httpbin):
-        files = {"file": open(__file__, "rb")}
         s = requests.Session()
-        req = requests.Request("POST", httpbin("post"), files=files)
-        prep = s.prepare_request(req)
+        with open(__file__, "rb") as f:
+            files = {"file": f}
+            req = requests.Request("POST", httpbin("post"), files=files)
+            prep = s.prepare_request(req)
         assert isinstance(prep.method, builtin_str)
         assert prep.method == "POST"
 
@@ -1084,18 +1094,14 @@ def test_non_prepared_request_error(self):
         assert str(e.value) == "You can only send PreparedRequests."
 
     def test_custom_content_type(self, httpbin):
-        r = requests.post(
-            httpbin("post"),
-            data={"stuff": json.dumps({"a": 123})},
-            files={
-                "file1": ("test_requests.py", open(__file__, "rb")),
-                "file2": (
-                    "test_requests",
-                    open(__file__, "rb"),
-                    "text/py-content-type",
-                ),
-            },
-        )
+        with open(__file__, "rb") as f1:
+            with open(__file__, "rb") as f2:
+                data={"stuff": json.dumps({"a": 123})}
+                files = {
+                    "file1": ("test_requests.py", f1),
+                    "file2": ("test_requests", f2, "text/py-content-type"),
+                }
+                r = requests.post(httpbin("post"), data=data, files=files)
         assert r.status_code == 200
         assert b"text/py-content-type" in r.request.body
 
@@ -1484,9 +1490,9 @@ def test_prepared_request_is_pickleable(self, httpbin):
         assert resp.status_code == 200
 
     def test_prepared_request_with_file_is_pickleable(self, httpbin):
-        files = {"file": open(__file__, "rb")}
-        r = requests.Request("POST", httpbin("post"), files=files)
-        p = r.prepare()
+        with open(__file__, "rb") as f:
+            r = requests.Request("POST", httpbin("post"), files={"file": f})
+            p = r.prepare()
 
         # Verify PreparedRequest can be pickled and unpickled
         r = pickle.loads(pickle.dumps(p))