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Bug: ERROR_NOT_SUPPORTED when installing packages with entrypoints on Windows NanoServer docker image (regression since uv==0.9.9) #18663

@cybops35

Description

@cybops35

Summary

uv fails to install packages that define entrypoints (console scripts) on Windows NanoServer (mcr.microsoft.com/windows/nanoserver:ltsc2022-KB5068787-amd64) with:

C:\>pip install uv==0.9.9
Collecting uv==0.9.9
  Downloading uv-0.9.9-py3-none-win_amd64.whl.metadata (12 kB)
Downloading uv-0.9.9-py3-none-win_amd64.whl (21.3 MB)
   ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 21.3/21.3 MB 1.0 MB/s  0:00:20
Installing collected packages: uv
  Attempting uninstall: uv
    Found existing installation: uv 0.9.8
    Uninstalling uv-0.9.8:
      Successfully uninstalled uv-0.9.8
Successfully installed uv-0.9.9

C:\>rd /s /q foo 

C:\>uv init foo  
Initialized project `foo` at `C:\foo`

C:\>uv --directory foo add docxcompose
Using CPython 3.11.9 interpreter at: C:\Program Files\Python311\python.exe
Creating virtual environment at: .venv
Resolved 6 packages in 24ms
error: Failed to install: docxcompose-2.1.0-py3-none-any.whl (docxcompose==2.1.0)
  Caused by: This function is not supported on this system. (os error -2147024776)

This is a regression introduced in uv 0.9.9.
uv 0.9.8 works correctly in the same environment.

C:\>pip install uv==0.9.8 
Collecting uv==0.9.8
  Downloading uv-0.9.8-py3-none-win_amd64.whl.metadata (12 kB)
Downloading uv-0.9.8-py3-none-win_amd64.whl (21.5 MB)
   ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 21.5/21.5 MB 1.1 MB/s  0:00:19
Installing collected packages: uv
  Attempting uninstall: uv
    Found existing installation: uv 0.9.7
    Uninstalling uv-0.9.7:
      Successfully uninstalled uv-0.9.7
Successfully installed uv-0.9.8

C:\>rd /s /q foo 

C:\>uv init foo  
Initialized project `foo` at `C:\foo`

C:\>uv --version
uv 0.9.8 (85c5d3228 2025-11-07)

C:\>uv --directory foo add docxcompose
Using CPython 3.11.9 interpreter at: C:\Program Files\Python311\python.exe
Creating virtual environment at: .venv
Resolved 6 packages in 18ms                                                                         
Installed 5 packages in 317ms
 + babel==2.18.0
 + docxcompose==2.1.0
 + lxml==6.0.2
 + python-docx==1.2.0
 + typing-extensions==4.15.0

According to the changelog it seems to come from:

Platform

mcr.microsoft.com/windows/nanoserver:ltsc2022-KB5068787-amd64

Version

0.9.9

Python version

CPython 3.11.9

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