diff --git a/3.16-rc/windows/windowsservercore-ltsc2022/Dockerfile b/3.16-rc/windows/windowsservercore-ltsc2022/Dockerfile
index 3a56cfc71..76d3db465 100644
--- a/3.16-rc/windows/windowsservercore-ltsc2022/Dockerfile
+++ b/3.16-rc/windows/windowsservercore-ltsc2022/Dockerfile
@@ -8,9 +8,6 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2022
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
 # PATH isn't actually set in the Docker image, so we have to set it from within the container
 RUN $newPath = ('C:\Python;C:\Python\Scripts;{0}' -f $env:PATH); \
 	Write-Host ('Updating PATH: {0}' -f $newPath); \
diff --git a/3.16-rc/windows/windowsservercore-ltsc2025/Dockerfile b/3.16-rc/windows/windowsservercore-ltsc2025/Dockerfile
index 266324f93..0fd8f90f4 100644
--- a/3.16-rc/windows/windowsservercore-ltsc2025/Dockerfile
+++ b/3.16-rc/windows/windowsservercore-ltsc2025/Dockerfile
@@ -8,9 +8,6 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2025
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
 # PATH isn't actually set in the Docker image, so we have to set it from within the container
 RUN $newPath = ('C:\Python;C:\Python\Scripts;{0}' -f $env:PATH); \
 	Write-Host ('Updating PATH: {0}' -f $newPath); \
diff --git a/Dockerfile-windows.template b/Dockerfile-windows.template
index bd69262f4..38ba650fe 100644
--- a/Dockerfile-windows.template
+++ b/Dockerfile-windows.template
@@ -1,4 +1,7 @@
 {{
+	def rcVersion:
+		env.version | rtrimstr("-rc")
+	;
 	def extension:
 		.checksums.windows.url | split(".")[-1]
 	;
@@ -8,9 +11,14 @@
 FROM mcr.microsoft.com/windows/{{ env.windowsVariant }}:{{ env.windowsRelease }}
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+{{ if rcVersion | IN("3.11", "3.12", "3.13", "3.14", "3.15") then ( -}}
 
+{{ # only set PYTHONIOENCODING on versions less than 3.16 -}}
 # https://github.com/docker-library/python/pull/557
 ENV PYTHONIOENCODING UTF-8
+{{ # reproducer: docker run --rm python:{{ env.version }}-windowsservercore-{{ env.windowsRelease }} python -c 'print(chr(0x4e2d))' -}}
+{{ # https://github.com/docker-library/python/pull/1144#pullrequestreview-5634536246 -}}
+{{ ) else "" end -}}
 {{
 	# installer sets path for older python, but needs to be set for the zip download
 	if is_windows_zip then (