diff --git a/pytest.ini b/pytest.ini
index c00b03296c..4e987c1a90 100644
--- a/pytest.ini
+++ b/pytest.ini
@@ -4,3 +4,10 @@ addopts = --tb=short
 markers =
     tests_internal_exceptions: Handle internal exceptions just as the SDK does, to test it. (Otherwise internal exceptions are recorded and reraised.)
     only: A temporary marker, to make pytest only run the tests with the mark, similar to jest's `it.only`. To use, run `pytest -v -m only`.
+
+[pytest-watch]
+; Enable this to drop into pdb on errors
+; pdb = True
+
+verbose = True
+nobeep = True
diff --git a/test-requirements.txt b/test-requirements.txt
index e513d05d4c..ea8333ca16 100644
--- a/test-requirements.txt
+++ b/test-requirements.txt
@@ -1,5 +1,6 @@
 pytest<7
 pytest-forked<=1.4.0
+pytest-watch==4.2.0
 tox==3.7.0
 Werkzeug
 pytest-localserver==0.5.0
diff --git a/tests/integrations/gcp/test_gcp.py b/tests/integrations/gcp/test_gcp.py
index 893aad0086..78ac8f2746 100644
--- a/tests/integrations/gcp/test_gcp.py
+++ b/tests/integrations/gcp/test_gcp.py
@@ -143,6 +143,8 @@ def inner(code, subprocess_kwargs=()):
                 else:
                     continue
 
+            stream.close()
+
         return envelope, event, return_value
 
     return inner
diff --git a/tests/integrations/stdlib/test_httplib.py b/tests/integrations/stdlib/test_httplib.py
index cffe00b074..c90f9eb891 100644
--- a/tests/integrations/stdlib/test_httplib.py
+++ b/tests/integrations/stdlib/test_httplib.py
@@ -76,7 +76,7 @@ def before_breadcrumb(crumb, hint):
         assert sys.getrefcount(response) == 2
 
 
-def test_httplib_misuse(sentry_init, capture_events):
+def test_httplib_misuse(sentry_init, capture_events, request):
     """HTTPConnection.getresponse must be called after every call to
     HTTPConnection.request. However, if somebody does not abide by
     this contract, we still should handle this gracefully and not
@@ -90,6 +90,10 @@ def test_httplib_misuse(sentry_init, capture_events):
     events = capture_events()
 
     conn = HTTPSConnection("httpbin.org", 443)
+
+    # make sure we release the resource, even if the test fails
+    request.addfinalizer(conn.close)
+
     conn.request("GET", "/anything/foo")
 
     with pytest.raises(Exception):
diff --git a/tox.ini b/tox.ini
index bc087ad23c..bd17e7fe58 100644
--- a/tox.ini
+++ b/tox.ini
@@ -93,6 +93,9 @@ deps =
     # with the -r flag
     -r test-requirements.txt
 
+    py3.4: colorama==0.4.1
+    py3.4: watchdog==0.10.7
+
     django-{1.11,2.0,2.1,2.2,3.0,3.1,3.2}: djangorestframework>=3.0.0,<4.0.0
 
     {py3.7,py3.8,py3.9,py3.10}-django-{1.11,2.0,2.1,2.2,3.0,3.1,3.2}: channels>2
@@ -308,10 +311,7 @@ commands =
     {py3.6,py3.7,py3.8,py3.9}-flask-{0.11}: pip install Werkzeug<2
 
     ; https://github.com/pallets/flask/issues/4455
-    {py3.7,py3.8,py3.9,py3.10}-flask-{0.11,0.12,1.0,1.1}: pip install "itsdangerous>=0.24,<2.0" "markupsafe<2.0.0"
-    ;"itsdangerous >= 0.24, < 2.0",
-;itsdangerous==1.1.0
-;markupsafe==1.1.1
+    {py3.7,py3.8,py3.9,py3.10}-flask-{0.11,0.12,1.0,1.1}: pip install "itsdangerous>=0.24,<2.0" "markupsafe<2.0.0" "jinja2<3.1.1"
 
     ; https://github.com/more-itertools/more-itertools/issues/578
     py3.5-flask-{0.10,0.11,0.12}: pip install more-itertools<8.11.0