docker-library
diff --git a/‎3.14-rc/windows/windowsservercore-1809/Dockerfile
+7 b/‎3.14-rc/windows/windowsservercore-1809/Dockerfile
+7
diff --git a/‎3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
+7 b/‎3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
+7
diff --git a/‎3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
+7 b/‎3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
+7
diff --git a/‎Dockerfile-windows.template
+9 b/‎Dockerfile-windows.template
+9
@@ -55,6 +55,15 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
 	\
+{{ if .version == "3.14.0b1" then ( -}}
+	Write-Host 'Reinstalling pip to workaround a bug ...'; \
+	# https://github.com/python/cpython/issues/133626
+	# clean up broken pip install
+	Remove-Item -Recurse C:\Python\Lib\site-packages\pip*; \
+	# install pip as pip.exe
+	python -m ensurepip --default-pip -vvv; \
+	\
+{{ ) else "" end -}}
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \
 	\
Original file line number	Diff line number	Diff line change
`@@ -55,6 +55,15 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en`
`55`	`55`	`\`
`56`	`56`	`$env:PYTHONDONTWRITEBYTECODE = '1'; \`
`57`	`57`	`\`
	`58`	`+{{ if .version == "3.14.0b1" then ( -}}`
	`59`	`+ Write-Host 'Reinstalling pip to workaround a bug ...'; \`
	`60`	`+ # https://github.com/python/cpython/issues/133626`
	`61`	`+ # clean up broken pip install`
	`62`	`+ Remove-Item -Recurse C:\Python\Lib\site-packages\pip*; \`
	`63`	`+ # install pip as pip.exe`
	`64`	`+ python -m ensurepip --default-pip -vvv; \`
	`65`	`+ \`
	`66`	`+{{ ) else "" end -}}`
`58`	`67`	`Write-Host 'Verifying pip install ...'; \`
`59`	`68`	`pip --version; \`
`60`	`69`	`\`