diff --git a/devscripts/run_tests.bat b/devscripts/run_tests.bat
index b8bb393d93..190d23918c 100644
--- a/devscripts/run_tests.bat
+++ b/devscripts/run_tests.bat
@@ -13,4 +13,5 @@ if ["%~1"]==[""] (
     exit /b 1
 )
 
+set PYTHONWARNINGS=error
 pytest %test_set%
diff --git a/devscripts/run_tests.sh b/devscripts/run_tests.sh
index c9a75ba006..e9904ae35d 100755
--- a/devscripts/run_tests.sh
+++ b/devscripts/run_tests.sh
@@ -11,4 +11,4 @@ else
     exit 1
 fi
 
-python3 -m pytest "$test_set"
+python3 -bb -Werror -m pytest "$test_set"
diff --git a/test/test_http.py b/test/test_http.py
index 029996ca93..d99be8be4e 100644
--- a/test/test_http.py
+++ b/test/test_http.py
@@ -66,8 +66,9 @@ class TestHTTPS(unittest.TestCase):
         certfn = os.path.join(TEST_DIR, 'testcert.pem')
         self.httpd = compat_http_server.HTTPServer(
             ('127.0.0.1', 0), HTTPTestRequestHandler)
-        self.httpd.socket = ssl.wrap_socket(
-            self.httpd.socket, certfile=certfn, server_side=True)
+        sslctx = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER)
+        sslctx.load_cert_chain(certfn, None)
+        self.httpd.socket = sslctx.wrap_socket(self.httpd.socket, server_side=True)
         self.port = http_server_port(self.httpd)
         self.server_thread = threading.Thread(target=self.httpd.serve_forever)
         self.server_thread.daemon = True
diff --git a/yt-dlp.cmd b/yt-dlp.cmd
index 2b651a41e4..aa4500f9f1 100644
--- a/yt-dlp.cmd
+++ b/yt-dlp.cmd
@@ -1 +1 @@
-@py "%~dp0yt_dlp\__main__.py" %*
\ No newline at end of file
+@py -bb -Werror -Xdev "%~dp0yt_dlp\__main__.py" %*
diff --git a/yt-dlp.sh b/yt-dlp.sh
index 71a9aa163a..0321a3362e 100755
--- a/yt-dlp.sh
+++ b/yt-dlp.sh
@@ -1,2 +1,2 @@
 #!/bin/sh
-exec python3 "$(dirname "$(realpath "$0")")/yt_dlp/__main__.py" "$@"
+exec "${PYTHON:-python3}" -bb -Werror -Xdev "$(dirname "$(realpath "$0")")/yt_dlp/__main__.py" "$@"
diff --git a/yt_dlp/compat.py b/yt_dlp/compat.py
index 9d3a6bbfd0..df0c54606e 100644
--- a/yt_dlp/compat.py
+++ b/yt_dlp/compat.py
@@ -159,7 +159,7 @@ def windows_enable_vt_mode():  # TODO: Do this the proper way https://bugs.pytho
     startupinfo = subprocess.STARTUPINFO()
     startupinfo.dwFlags |= subprocess.STARTF_USESHOWWINDOW
     try:
-        subprocess.Popen('', shell=True, startupinfo=startupinfo)
+        subprocess.Popen('', shell=True, startupinfo=startupinfo).wait()
         WINDOWS_VT_MODE = True
     except Exception:
         pass
diff --git a/yt_dlp/extractor/gedidigital.py b/yt_dlp/extractor/gedidigital.py
index c878daff82..4ae5362b4d 100644
--- a/yt_dlp/extractor/gedidigital.py
+++ b/yt_dlp/extractor/gedidigital.py
@@ -11,7 +11,7 @@ from ..utils import (
 
 
 class GediDigitalIE(InfoExtractor):
-    _VALID_URL = r'''(?x)(?P<url>(?:https?:)//video\.
+    _VALID_URL = r'''(?x:(?P<url>(?:https?:)//video\.
         (?:
             (?:
                 (?:espresso\.)?repubblica
@@ -33,7 +33,7 @@ class GediDigitalIE(InfoExtractor):
                 |corrierealpi
                 |lasentinella
             )\.gelocal
-        )\.it(?:/[^/]+){2,4}/(?P<id>\d+))(?:$|[?&].*)'''
+        )\.it(?:/[^/]+){2,4}/(?P<id>\d+))(?:$|[?&].*))'''
     _TESTS = [{
         'url': 'https://video.lastampa.it/politica/il-paradosso-delle-regionali-la-lega-vince-ma-sembra-aver-perso/121559/121683',
         'md5': '84658d7fb9e55a6e57ecc77b73137494',
diff --git a/yt_dlp/extractor/gfycat.py b/yt_dlp/extractor/gfycat.py
index 7373c574ff..60f06ccd78 100644
--- a/yt_dlp/extractor/gfycat.py
+++ b/yt_dlp/extractor/gfycat.py
@@ -10,7 +10,7 @@ from ..utils import (
 
 
 class GfycatIE(InfoExtractor):
-    _VALID_URL = r'(?i)https?://(?:(?:www|giant|thumbs)\.)?gfycat\.com/(?:ru/|ifr/|gifs/detail/)?(?P<id>[^-/?#\."\']+)'
+    _VALID_URL = r'https?://(?:(?:www|giant|thumbs)\.)?gfycat\.com/(?i:ru/|ifr/|gifs/detail/)?(?P<id>[^-/?#\."\']+)'
     _TESTS = [{
         'url': 'http://gfycat.com/DeadlyDecisiveGermanpinscher',
         'info_dict': {
diff --git a/yt_dlp/extractor/wimtv.py b/yt_dlp/extractor/wimtv.py
index 6e7ec3436f..263844d72b 100644
--- a/yt_dlp/extractor/wimtv.py
+++ b/yt_dlp/extractor/wimtv.py
@@ -12,14 +12,14 @@ from ..utils import (
 class WimTVIE(InfoExtractor):
     _player = None
     _UUID_RE = r'[\da-f]{8}-[\da-f]{4}-[\da-f]{4}-[\da-f]{4}-[\da-f]{12}'
-    _VALID_URL = r'''(?x)
+    _VALID_URL = r'''(?x:
         https?://platform.wim.tv/
         (?:
             (?:embed/)?\?
             |\#/webtv/.+?/
         )
         (?P<type>vod|live|cast)[=/]
-        (?P<id>%s).*?''' % _UUID_RE
+        (?P<id>%s).*?)''' % _UUID_RE
     _TESTS = [{
         # vod stream
         'url': 'https://platform.wim.tv/embed/?vod=db29fb32-bade-47b6-a3a6-cb69fe80267a',