diff --git a/3.10/alpine3.20/Dockerfile b/3.10/alpine3.20/Dockerfile
index 904d78274..b46a12d48 100644
--- a/3.10/alpine3.20/Dockerfile
+++ b/3.10/alpine3.20/Dockerfile
@@ -124,7 +124,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.10/alpine3.21/Dockerfile b/3.10/alpine3.21/Dockerfile
index f50ab034d..3c03960a8 100644
--- a/3.10/alpine3.21/Dockerfile
+++ b/3.10/alpine3.21/Dockerfile
@@ -124,7 +124,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.10/bookworm/Dockerfile b/3.10/bookworm/Dockerfile
index 7077b6ad9..ddc2cfe13 100644
--- a/3.10/bookworm/Dockerfile
+++ b/3.10/bookworm/Dockerfile
@@ -96,7 +96,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.10/bullseye/Dockerfile b/3.10/bullseye/Dockerfile
index c68c3fa98..ef1ad6771 100644
--- a/3.10/bullseye/Dockerfile
+++ b/3.10/bullseye/Dockerfile
@@ -96,7 +96,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.10/slim-bookworm/Dockerfile b/3.10/slim-bookworm/Dockerfile
index c6c7b7e3b..8c3a84d47 100644
--- a/3.10/slim-bookworm/Dockerfile
+++ b/3.10/slim-bookworm/Dockerfile
@@ -129,7 +129,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.10/slim-bullseye/Dockerfile b/3.10/slim-bullseye/Dockerfile
index 21e9cd821..eee742510 100644
--- a/3.10/slim-bullseye/Dockerfile
+++ b/3.10/slim-bullseye/Dockerfile
@@ -129,7 +129,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.11/alpine3.20/Dockerfile b/3.11/alpine3.20/Dockerfile
index 569550e17..6bfbfc584 100644
--- a/3.11/alpine3.20/Dockerfile
+++ b/3.11/alpine3.20/Dockerfile
@@ -124,7 +124,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.11/alpine3.21/Dockerfile b/3.11/alpine3.21/Dockerfile
index 0c4ae403a..858ce0232 100644
--- a/3.11/alpine3.21/Dockerfile
+++ b/3.11/alpine3.21/Dockerfile
@@ -124,7 +124,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.11/bookworm/Dockerfile b/3.11/bookworm/Dockerfile
index 8d9f24fb5..943aa0150 100644
--- a/3.11/bookworm/Dockerfile
+++ b/3.11/bookworm/Dockerfile
@@ -96,7 +96,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.11/bullseye/Dockerfile b/3.11/bullseye/Dockerfile
index 03891a315..cad17e31e 100644
--- a/3.11/bullseye/Dockerfile
+++ b/3.11/bullseye/Dockerfile
@@ -96,7 +96,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.11/slim-bookworm/Dockerfile b/3.11/slim-bookworm/Dockerfile
index 91d62309d..1d77b85f6 100644
--- a/3.11/slim-bookworm/Dockerfile
+++ b/3.11/slim-bookworm/Dockerfile
@@ -129,7 +129,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.11/slim-bullseye/Dockerfile b/3.11/slim-bullseye/Dockerfile
index 91175b24c..250c1c031 100644
--- a/3.11/slim-bullseye/Dockerfile
+++ b/3.11/slim-bullseye/Dockerfile
@@ -129,7 +129,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==65.5.1' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.9/alpine3.20/Dockerfile b/3.9/alpine3.20/Dockerfile
index f0d2d7d2b..35e8fef9c 100644
--- a/3.9/alpine3.20/Dockerfile
+++ b/3.9/alpine3.20/Dockerfile
@@ -123,7 +123,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==58.1.0' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.9/alpine3.21/Dockerfile b/3.9/alpine3.21/Dockerfile
index 421650c04..a5f0d963f 100644
--- a/3.9/alpine3.21/Dockerfile
+++ b/3.9/alpine3.21/Dockerfile
@@ -123,7 +123,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==58.1.0' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.9/bookworm/Dockerfile b/3.9/bookworm/Dockerfile
index 2c4863f3b..98de1f753 100644
--- a/3.9/bookworm/Dockerfile
+++ b/3.9/bookworm/Dockerfile
@@ -95,7 +95,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==58.1.0' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.9/bullseye/Dockerfile b/3.9/bullseye/Dockerfile
index 8333aa2c4..afc057b96 100644
--- a/3.9/bullseye/Dockerfile
+++ b/3.9/bullseye/Dockerfile
@@ -95,7 +95,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==58.1.0' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.9/slim-bookworm/Dockerfile b/3.9/slim-bookworm/Dockerfile
index 0457d581a..19b1b68ce 100644
--- a/3.9/slim-bookworm/Dockerfile
+++ b/3.9/slim-bookworm/Dockerfile
@@ -128,7 +128,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==58.1.0' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/3.9/slim-bullseye/Dockerfile b/3.9/slim-bullseye/Dockerfile
index df12ba8a4..ed73ba93a 100644
--- a/3.9/slim-bullseye/Dockerfile
+++ b/3.9/slim-bullseye/Dockerfile
@@ -128,7 +128,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		'setuptools==58.1.0' \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 	pip3 --version
 
diff --git a/Dockerfile-linux.template b/Dockerfile-linux.template
index f0f3a82f6..7c62579cf 100644
--- a/Dockerfile-linux.template
+++ b/Dockerfile-linux.template
@@ -301,7 +301,8 @@ RUN set -eux; \
 		--no-cache-dir \
 		--no-compile \
 		{{ "setuptools==\( .setuptools.version )" | @sh }} \
-		wheel \
+		# https://github.com/docker-library/python/issues/1023
+		'wheel<0.46' \
 	; \
 {{ ) else "" end -}}
 	pip3 --version
diff --git a/Dockerfile-windows.template b/Dockerfile-windows.template
index a564f29de..add70eac7 100644
--- a/Dockerfile-windows.template
+++ b/Dockerfile-windows.template
@@ -54,17 +54,6 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	Remove-Item $env:TEMP/Python*.log -Force; \
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
-{{ if .setuptools then ( -}}
-	\
-	Write-Host ('Installing setuptools and wheel ...'); \
-	pip install \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		--no-compile \
-		'setuptools=={{ .setuptools.version }}' \
-		wheel \
-	; \
-{{ ) else "" end -}}
 	\
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \