Unable to access runtimes index on Windows Server 2019

[Jackenmen]

Describe the bug
I'm not sure if there are any specific configuration steps that need to be taken for PyManager to work on Windows Server 2019, but I'm running into the following:

********************************************************************************
[ERROR] Unable to access runtimes index at https://www.python.org/ftp/python/index-windows.json: The parameter is incorrect.
[ERROR] Unable to find runtimes index at file:///C:/Program Files/PyManager/bundled/fallback-index.json
[ERROR] An error occurred. Please check any output above, or the log file, and try again.
Log file for this session: C:\Users\ADMINI~1\AppData\Local\Temp\2\python_install_20250515025034_1836.log
If you cannot resolve it yourself, please report the error with your log file at https://github.com/python/pymanager
To see all available commands, run 'py help'
********************************************************************************
[ERROR] Internal error 0x00000057. Please report to https://github.com/python/pymanager

It would seem that the download is failing and there was no fallback index bundled (probably just with the MSI install?).

To Reproduce
Steps to reproduce the behaviour:

1. Make a fresh install of Windows Server 2019 Standard with Desktop Experience (e.g. evaluation copy ISO download from Microsoft: https://www.microsoft.com/en-us/evalcenter/download-windows-server-2019)
2. Install MSI from https://www.python.org/ftp/python/pymanager/python-manager-25.0b6.msi
3. Run py in a fresh Windows PowerShell window.
4. See error.

Expected behavior
Probably no download issues 😄
Considering that the error says "The parameter is incorrect", it seems like it might not be a configuration issue on my part but I don't actually know for sure, it's not a particularly descriptive error.

Additional context

Log file content:

>> Writing logs to C:\Users\ADMINI~1\AppData\Local\Temp\2\python_install_20250515025034_1836.log
>> Python installation manager 25.0b7
Copyright (c) Python Software Foundation. All Rights Reserved.

BEGIN install_command.execute: []
>  ********************************************************************************
Reading installs from C:\Users\Administrator\AppData\Local\Python
Found 0 installs
Calculating default install
Filtering installs by tag = 3.14
tag '3.14' matched 0 installs
default_platform '-64' matched 0 installs
Reusing unfiltered list
Searching https://www.python.org/ftp/python/index-windows.json
>> Searching for Python matching 3.14
Selecting package with tag=3.14 and platform=-64
Fetching: https://www.python.org/ftp/python/index-windows.json
winhttp_urlopen: https://www.python.org/ftp/python/index-windows.json
>> Failed to download using WinHTTP. Retrying with fallback method.
ERROR:
Traceback (most recent call last):
  File "manage\urlutils.py", line 361, in urlopen
  File "manage\urlutils.py", line 174, in _winhttp_urlopen
OSError: [WinError 87] The parameter is incorrect.

urllib download unavailable - using fallback
>> Failed to download using PowerShell. Retrying with fallback method.
ERROR:
Traceback (most recent call last):
  File "manage\urlutils.py", line 398, in urlopen
  File "manage\urlutils.py", line 272, in _powershell_urlopen
  File "manage\urlutils.py", line 286, in _powershell_urlretrieve
  File "manage\urlutils.py", line 89, in on_auth_request
  File "manage\urlutils.py", line 642, in on_auth
KeyError: 'https://www.python.org/ftp/python/index-windows.json'

!! Unable to access runtimes index at https://www.python.org/ftp/python/index-windows.json: The parameter is incorrect.
Capturing error in case fallbacks fail
Traceback (most recent call last):
  File "manage\install_command.py", line 719, in execute
  File "manage\install_command.py", line 394, in _find_one
  File "manage\install_command.py", line 66, in select_package
  File "manage\urlutils.py", line 660, in __next__
  File "manage\urlutils.py", line 408, in urlopen
  File "manage\urlutils.py", line 361, in urlopen
  File "manage\urlutils.py", line 174, in _winhttp_urlopen
OSError: [WinError 87] The parameter is incorrect.

Searching file:///C:/Program Files/PyManager/bundled/fallback-index.json
>> Searching for Python matching 3.14
Selecting package with tag=3.14 and platform=-64
Fetching: file:///C:/Program Files/PyManager/bundled/fallback-index.json
!! Unable to find runtimes index at file:///C:/Program Files/PyManager/bundled/fallback-index.json
Capturing error in case fallbacks fail
Traceback (most recent call last):
  File "manage\install_command.py", line 719, in execute
  File "manage\install_command.py", line 394, in _find_one
  File "manage\install_command.py", line 66, in select_package
  File "manage\urlutils.py", line 660, in __next__
  File "manage\urlutils.py", line 350, in urlopen
FileNotFoundError: [Errno 2] No such file or directory: 'C:\\Program Files\\PyManager\\bundled\\fallback-index.json'

!! An error occurred. Please check any output above, or the log file, and try again.
>  Log file for this session: C:\Users\ADMINI~1\AppData\Local\Temp\2\python_install_20250515025034_1836.log
>  If you cannot resolve it yourself, please report the error with your log file at https://github.com/python/pymanager
TRACEBACK:
Traceback (most recent call last):
  File "manage\install_command.py", line 734, in execute
  File "manage\install_command.py", line 719, in execute
  File "manage\install_command.py", line 394, in _find_one
  File "manage\install_command.py", line 66, in select_package
  File "manage\urlutils.py", line 660, in __next__
  File "manage\urlutils.py", line 408, in urlopen
  File "manage\urlutils.py", line 361, in urlopen
  File "manage\urlutils.py", line 174, in _winhttp_urlopen
OSError: [WinError 87] The parameter is incorrect.

>  To see all available commands, run 'py help'
>  ********************************************************************************
END install_command.execute
SILENCED ERROR
Traceback (most recent call last):
  File "manage\install_command.py", line 734, in execute
  File "manage\install_command.py", line 719, in execute
  File "manage\install_command.py", line 394, in _find_one
  File "manage\install_command.py", line 66, in select_package
  File "manage\urlutils.py", line 660, in __next__
  File "manage\urlutils.py", line 408, in urlopen
  File "manage\urlutils.py", line 361, in urlopen
  File "manage\urlutils.py", line 174, in _winhttp_urlopen
OSError: [WinError 87] The parameter is incorrect.

The above exception was the direct cause of the following exception:

Traceback (most recent call last):
  File "manage\__init__.py", line 50, in main
  File "manage\commands.py", line 820, in execute
  File "manage\install_command.py", line 752, in execute
  File "manage\install_command.py", line 551, in _fatal_install_error
SystemExit: 87

[zooba]

It would seem that the download is failing and there was no fallback index bundled (probably just with the MSI install?).

Correct, no fallback in the MSI. The assumption is that when it's deployed, whoever is managing that will also decide what goes with it (if anything). Bundling Python would force the MSI size to about 50MB, which is also a large overhead for some network-based deployments.

Considering that the error says "The parameter is incorrect", it seems like it might not be a configuration issue on my part but I don't actually know for sure, it's not a particularly descriptive error.

Yeah, it's not. And it may still be something that can be resolved with configuration, but more likely I'm just passing an argument that didn't exist on WS2019.

This looks like a real error:

ERROR:
Traceback (most recent call last):
  File "manage\urlutils.py", line 398, in urlopen
  File "manage\urlutils.py", line 272, in _powershell_urlopen
  File "manage\urlutils.py", line 286, in _powershell_urlretrieve
  File "manage\urlutils.py", line 89, in on_auth_request
  File "manage\urlutils.py", line 642, in on_auth
KeyError: 'https://www.python.org/ftp/python/index-windows.json'

I don't remember whether auth is unconditional for PowerShell (was kinda hoping nobody would ever need it 😉 ), but it may just be that.

---

Anyway, thanks for the detailed report. Looks like I'm setting up some Windows Server test machines today...