Title: `pip` is failing to run on Windows 11 25H2. · Issue #8281 · RustPython/RustPython · GitHub
Open Graph Title: `pip` is failing to run on Windows 11 25H2. · Issue #8281 · RustPython/RustPython
X Title: `pip` is failing to run on Windows 11 25H2. · Issue #8281 · RustPython/RustPython
Description: Rustpython's pip is failing to run on Windows 11 25H2. Error: C:\Windows\System32>pip install pillow WARNING: There was an error checking the latest version of pip. ERROR: Exception: Traceback (most recent call last): File "C:\Users\Viní...
Open Graph Description: Rustpython's pip is failing to run on Windows 11 25H2. Error: C:\Windows\System32>pip install pillow WARNING: There was an error checking the latest version of pip. ERROR: Exception: Traceback (mos...
X Description: Rustpython's pip is failing to run on Windows 11 25H2. Error: C:\Windows\System32>pip install pillow WARNING: There was an error checking the latest version of pip. ERROR: Exception: Traceba...
Opengraph URL: https://github.com/RustPython/RustPython/issues/8281
X: @github
Domain: github.com
{"@context":"https://schema.org","@type":"DiscussionForumPosting","headline":"`pip` is failing to run on Windows 11 25H2.","articleBody":"Rustpython's `pip` is failing to run on Windows 11 25H2.\n\nError:\n```yaml\nC:\\Windows\\System32\u003epip install pillow\nWARNING: There was an error checking the latest version of pip.\nERROR: Exception:\nTraceback (most recent call last):\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\truststore\\_windows.py\", line 340, in _verify_peercerts_impl\n CertAddEncodedCertificateToStore(\n ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^\n hIntermediateCertStore,\n ^^^^^^^^^^^^^^^^^^^^^^^\n ...\u003c4 lines\u003e...\n None,\n ^^^^^\n )\n ^\nTypeError: wrong type\n\nDuring handling of the above exception, another exception occurred:\n\nTraceback (most recent call last):\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\cli\\base_command.py\", line 109, in _run_wrapper\n status = _inner_run()\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\cli\\base_command.py\", line 102, in _inner_run\n return self.run(options, args)\n ~~~~~~~~^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\cli\\req_command.py\", line 101, in wrapper\n return func(self, options, args)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\commands\\install.py\", line 479, in run\n requirement_set = resolver.resolve(\n reqs, check_supported_wheels=not options.target_dir\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\resolution\\resolvelib\\resolver.py\", line 99, in resolve\n result = self._result = resolver.resolve(\n ~~~~~~~~~~~~~~~~^\n collected.requirements, max_rounds=limit_how_complex_resolution_can_be\n ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n )\n ^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\resolvelib\\resolvers\\resolution.py\", line 601, in resolve\n state = resolution.resolve(requirements, max_rounds=max_rounds)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\resolvelib\\resolvers\\resolution.py\", line 434, in resolve\n self._add_to_criteria(self.state.criteria, r, parent=None)\n ~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\resolvelib\\resolvers\\resolution.py\", line 150, in _add_to_criteria\n if not criterion.candidates:\n ^^^^^^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\resolvelib\\structs.py\", line 194, in __bool__\n return bool(self._sequence)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\resolution\\resolvelib\\found_candidates.py\", line 165, in __bool__\n self._bool = any(self)\n ~~~^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\resolution\\resolvelib\\found_candidates.py\", line 149, in \u003cgenexpr\u003e\n return (c for c in iterator if id(c) not in self._incompatible_ids)\n ^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\resolution\\resolvelib\\found_candidates.py\", line 35, in _iter_built\n for version, func in infos:\n ^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\resolution\\resolvelib\\factory.py\", line 346, in iter_index_candidate_infos\n result = self._finder.find_best_candidate(\n project_name=name,\n specifier=specifier,\n hashes=hashes,\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\package_finder.py\", line 959, in find_best_candidate\n candidates = self.find_all_candidates(project_name)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\package_finder.py\", line 896, in find_all_candidates\n page_candidates = list(page_candidates_it)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\sources.py\", line 196, in page_candidates\n yield from self._candidates_from_page(self._link)\n ~~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\package_finder.py\", line 854, in process_project_url\n index_response = self._link_collector.fetch_response(project_url)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\collector.py\", line 442, in fetch_response\n return _get_index_content(location, session=self.session)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\collector.py\", line 346, in _get_index_content\n resp = _get_simple_response(url, session=session)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\index\\collector.py\", line 126, in _get_simple_response\n resp = session.get(\n url,\n ...\u003c22 lines\u003e...\n },\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\requests\\sessions.py\", line 605, in get\n return self.request(\"GET\", url, **kwargs)\n ~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_internal\\network\\session.py\", line 537, in request\n return super().request(method, url, *args, **kwargs)\n ~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\requests\\sessions.py\", line 592, in request\n resp = self.send(prep, **send_kwargs)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\requests\\sessions.py\", line 706, in send\n r = adapter.send(request, **kwargs)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\cachecontrol\\adapter.py\", line 76, in send\n resp = super().send(request, stream, timeout, verify, cert, proxies)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\requests\\adapters.py\", line 645, in send\n resp = conn.urlopen(\n method=request.method,\n ...\u003c9 lines\u003e...\n chunked=chunked,\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\connectionpool.py\", line 787, in urlopen\n response = self._make_request(\n conn,\n ...\u003c10 lines\u003e...\n **response_kw,\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\connectionpool.py\", line 464, in _make_request\n self._validate_conn(conn)\n ~~~~~~~~~~~~~~~~~~~^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\connectionpool.py\", line 1093, in _validate_conn\n conn.connect()\n ~~~~~~~~~~~~^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\connection.py\", line 796, in connect\n sock_and_verified = _ssl_wrap_socket_and_match_hostname(\n sock=sock,\n ...\u003c14 lines\u003e...\n assert_fingerprint=self.assert_fingerprint,\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\connection.py\", line 975, in _ssl_wrap_socket_and_match_hostname\n ssl_sock = ssl_wrap_socket(\n sock=sock,\n ...\u003c8 lines\u003e...\n tls_in_tls=tls_in_tls,\n )\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\util\\ssl_.py\", line 483, in ssl_wrap_socket\n ssl_sock = _ssl_wrap_socket_impl(sock, context, tls_in_tls, server_hostname)\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\urllib3\\util\\ssl_.py\", line 527, in _ssl_wrap_socket_impl\n return ssl_context.wrap_socket(sock, server_hostname=server_hostname)\n ~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\truststore\\_api.py\", line 130, in wrap_socket\n _verify_peercerts(ssl_sock, server_hostname=server_hostname)\n ~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\truststore\\_api.py\", line 339, in _verify_peercerts\n _verify_peercerts_impl(\n ~~~~~~~~~~~~~~~~~~~~~~^\n sock_or_sslobj.context, cert_bytes, server_hostname=server_hostname\n ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n )\n ^\n File \"C:\\Users\\Vinícius\\.cargo\\bin\\Lib\\site-packages\\pip\\_vendor\\truststore\\_windows.py\", line 410, in _verify_peercerts_impl\n CertCloseStore(hIntermediateCertStore, 0)\n ~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^\nTypeError: wrong type\n```\n\nSysteminfo:\n```yaml\nHost Name: LAPTOP-SAMSUNG\nOS Name: Microsoft Windows 11 Pro\nOS Version: 10.0.26200 N/A Build 26200\nOS Manufacturer: Microsoft Corporation\nOS Configuration: Standalone Workstation\nOS Build Type: Multiprocessor Free\nRegistered Owner: Vinícius\nRegistered Organization: N/A\nProduct ID: 00330-80000-00000-AA411\nOriginal Install Date: 4/7/2026, 9:23:11 PM\nSystem Boot Time: 7/13/2026, 12:38:16 PM\nSystem Manufacturer: SAMSUNG ELECTRONICS CO., LTD.\nSystem Model: 550XDA\nSystem Type: x64-based PC\nProcessor(s): 1 Processor(s) Installed.\n [01]: Intel64 Family 6 Model 140 Stepping 1 GenuineIntel ~1805 Mhz\nBIOS Version: American Megatrends International, LLC. P23CFB.053.241029.HQ, 10/29/2024\nWindows Directory: C:\\WINDOWS\nSystem Directory: C:\\WINDOWS\\system32\nBoot Device: \\Device\\HarddiskVolume1\nSystem Locale: pt-br;Portuguese (Brazil)\nInput Locale: pt-br;Portuguese (Brazil)\nTime Zone: (UTC-03:00) Brasilia\nTotal Physical Memory: 3,820 MB\nAvailable Physical Memory: 418 MB\nVirtual Memory: Max Size: 10,220 MB\nVirtual Memory: Available: 4,506 MB\nVirtual Memory: In Use: 5,714 MB\nPage File Location(s): C:\\pagefile.sys\nDomain: WORKGROUP\nLogon Server: \\\\LAPTOP-SAMSUNG\nHotfix(s): 5 Hotfix(s) Installed.\n [01]: KB5087051\n [02]: KB5054156\n [03]: KB5094126\n [04]: KB5083532\n [05]: KB5094135\nNetwork Card(s): 3 NIC(s) Installed.\n [01]: Intel(R) Wireless-AC 9462\n Connection Name: Wi-Fi\n DHCP Enabled: Yes\n DHCP Server: 192.168.0.1\n IP address(es)\n [01]: 192.168.0.38\n [02]: fe80::c675:abff:fe69:a0b9\n [03]: 2804:2f30:fc02:da00:c675:abff:fe69:a0b9\n [02]: Realtek PCIe GbE Family Controller\n Connection Name: Ethernet\n Status: Media disconnected\n [03]: VirtualBox Host-Only Ethernet Adapter\n Connection Name: Ethernet 2\n DHCP Enabled: No\n IP address(es)\n [01]: 192.168.56.1\n [02]: fe80::800:27ff:fe00:3c\nVirtualization-based security: Status: Running\n Required Security Properties:\n DMA Protection\n Available Security Properties:\n Base Virtualization Support\n Secure Boot\n DMA Protection\n Secure Memory Overwrite\n UEFI Code Read-Only\n SMM Security Mitigations 1.0\n Mode Based Execution Control\n APIC Virtualization\n Services Configured:\n Services Running:\n App Control for Business policy: Enforced\n App Control for Business user mode policy: Enforced\n Enabled Security Features:\nHyper-V Requirements: A hypervisor has been detected. Features required for Hyper-V will not be displayed.\n```","author":{"url":"https://github.com/CVFA1","@type":"Person","name":"CVFA1"},"datePublished":"2026-07-13T18:44:49.000Z","interactionStatistic":{"@type":"InteractionCounter","interactionType":"https://schema.org/CommentAction","userInteractionCount":6},"url":"https://github.com/8281/RustPython/issues/8281"}
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