diff --git a/requirements/app/app.txt b/requirements/app/app.txt
index d2bffc5cecfd3..a59e0b5ca5c28 100644
--- a/requirements/app/app.txt
+++ b/requirements/app/app.txt
@@ -23,7 +23,7 @@ Jinja2 <3.2.0
 PyYAML <=6.0.1
 requests <2.32.0
 rich >=12.3.0, <13.6.0
-urllib3 <2.1.0
+urllib3 <2.0.0
 uvicorn <0.24.0
 websocket-client <1.7.0
 websockets <11.1.0
diff --git a/tests/tests_app/cli/test_cmd_launch.py b/tests/tests_app/cli/test_cmd_launch.py
index 4b75c08de5dce..167e896fba11c 100644
--- a/tests/tests_app/cli/test_cmd_launch.py
+++ b/tests/tests_app/cli/test_cmd_launch.py
@@ -7,6 +7,7 @@
 from unittest import mock
 from unittest.mock import ANY, MagicMock, Mock
 
+import pytest
 from click.testing import CliRunner
 from lightning.app.cli.lightning_cli_launch import run_flow, run_flow_and_servers, run_frontend, run_server
 from lightning.app.core.queues import QueuingSystem
@@ -189,6 +190,7 @@ def start_processes(**functions):
 
 
 @_RunIf(skip_windows=True)
+@pytest.mark.flaky(reruns=3)
 def test_manage_server_processes_one_process_gets_killed(capfd):
     functions = {"p1": run_forever_process, "p2": run_for_2_seconds_and_raise}
     p = Process(target=start_processes, kwargs=functions)
diff --git a/tests/tests_app/core/test_lightning_api.py b/tests/tests_app/core/test_lightning_api.py
index 65ac6fcab2bf7..9b80d540c17e0 100644
--- a/tests/tests_app/core/test_lightning_api.py
+++ b/tests/tests_app/core/test_lightning_api.py
@@ -404,7 +404,7 @@ async def test_frontend_routes(path, expected_status_code):
     assert response.status_code == expected_status_code
 
 
-@pytest.mark.xfail(sys.platform == "linux", reason="No idea why... need to be fixed")  # fixme
+@pytest.mark.xfail(sys.platform == "linux", strict=False, reason="No idea why... need to be fixed")  # fixme
 def test_start_server_started():
     """This test ensures has_started_queue receives a signal when the REST API has started."""
     api_publish_state_queue = mp.Queue()
diff --git a/tests/tests_app/core/test_lightning_app.py b/tests/tests_app/core/test_lightning_app.py
index 08a2d7c641b29..a70cbb853e437 100644
--- a/tests/tests_app/core/test_lightning_app.py
+++ b/tests/tests_app/core/test_lightning_app.py
@@ -1084,6 +1084,7 @@ def run_once(self):
         return res
 
 
+@pytest.mark.flaky(reruns=3)
 def test_lightning_app_has_updated():
     app = TestLightningHasUpdatedApp(FlowPath())
     MultiProcessRuntime(app, start_server=False).dispatch()
diff --git a/tests/tests_app/utilities/test_network.py b/tests/tests_app/utilities/test_network.py
index 3a14c0301ef1e..999c75da57dd7 100644
--- a/tests/tests_app/utilities/test_network.py
+++ b/tests/tests_app/utilities/test_network.py
@@ -48,10 +48,10 @@ def test_find_free_network_port_cloudspace(_, patch_constants):
 @mock.patch("urllib3.connectionpool.HTTPConnectionPool._get_conn")
 def test_http_client_retry_post(getconn_mock):
     getconn_mock.return_value.getresponse.side_effect = [
-        mock.Mock(status=500, msg=HTTPMessage()),
-        mock.Mock(status=599, msg=HTTPMessage()),
-        mock.Mock(status=405, msg=HTTPMessage()),
-        mock.Mock(status=200, msg=HTTPMessage()),
+        mock.Mock(status=500, msg=HTTPMessage(), headers={}),
+        mock.Mock(status=599, msg=HTTPMessage(), headers={}),
+        mock.Mock(status=405, msg=HTTPMessage(), headers={}),
+        mock.Mock(status=200, msg=HTTPMessage(), headers={}),
     ]
 
     client = HTTPClient(base_url="http://test.url")
@@ -69,10 +69,10 @@ def test_http_client_retry_post(getconn_mock):
 @mock.patch("urllib3.connectionpool.HTTPConnectionPool._get_conn")
 def test_http_client_retry_get(getconn_mock):
     getconn_mock.return_value.getresponse.side_effect = [
-        mock.Mock(status=500, msg=HTTPMessage()),
-        mock.Mock(status=599, msg=HTTPMessage()),
-        mock.Mock(status=405, msg=HTTPMessage()),
-        mock.Mock(status=200, msg=HTTPMessage()),
+        mock.Mock(status=500, msg=HTTPMessage(), headers={}),
+        mock.Mock(status=599, msg=HTTPMessage(), headers={}),
+        mock.Mock(status=405, msg=HTTPMessage(), headers={}),
+        mock.Mock(status=200, msg=HTTPMessage(), headers={}),
     ]
 
     client = HTTPClient(base_url="http://test.url")