diff --git a/3.14-rc/windows/windowsservercore-1809/Dockerfile b/3.14-rc/windows/windowsservercore-1809/Dockerfile
index ca6012734..61a8ce521 100644
--- a/3.14-rc/windows/windowsservercore-1809/Dockerfile
+++ b/3.14-rc/windows/windowsservercore-1809/Dockerfile
@@ -57,6 +57,13 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
 	\
+	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; \
+	\
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \
 	\
diff --git a/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile b/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
index d177ea7b6..75ffda7b0 100644
--- a/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
+++ b/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
@@ -57,6 +57,13 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
 	\
+	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; \
+	\
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \
 	\
diff --git a/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile b/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
index 5d3b7d088..ffc2b344d 100644
--- a/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
+++ b/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
@@ -57,6 +57,13 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
 	\
+	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; \
+	\
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \
 	\
diff --git a/Dockerfile-windows.template b/Dockerfile-windows.template
index add70eac7..115b08c21 100644
--- a/Dockerfile-windows.template
+++ b/Dockerfile-windows.template
@@ -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; \
 	\