diff --git a/3.10-rc/windows/windowsservercore-1809/Dockerfile b/3.10-rc/windows/windowsservercore-1809/Dockerfile
index 8eebba50f..b4ef99351 100644
--- a/3.10-rc/windows/windowsservercore-1809/Dockerfile
+++ b/3.10-rc/windows/windowsservercore-1809/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.10.0a1
 ENV PYTHON_RELEASE 3.10.0
 
diff --git a/3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile b/3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile
index 81e68b024..c62cd80bf 100644
--- a/3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.10.0a1
 ENV PYTHON_RELEASE 3.10.0
 
diff --git a/3.7/windows/windowsservercore-1809/Dockerfile b/3.7/windows/windowsservercore-1809/Dockerfile
index 94d187a97..184a3b62e 100644
--- a/3.7/windows/windowsservercore-1809/Dockerfile
+++ b/3.7/windows/windowsservercore-1809/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.7.9
 ENV PYTHON_RELEASE 3.7.9
 
diff --git a/3.7/windows/windowsservercore-ltsc2016/Dockerfile b/3.7/windows/windowsservercore-ltsc2016/Dockerfile
index 7cb86738a..b75ea5c57 100644
--- a/3.7/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.7/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.7.9
 ENV PYTHON_RELEASE 3.7.9
 
diff --git a/3.8/windows/windowsservercore-1809/Dockerfile b/3.8/windows/windowsservercore-1809/Dockerfile
index 9a8302665..3f7ba0ad9 100644
--- a/3.8/windows/windowsservercore-1809/Dockerfile
+++ b/3.8/windows/windowsservercore-1809/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.8.6
 ENV PYTHON_RELEASE 3.8.6
 
diff --git a/3.8/windows/windowsservercore-ltsc2016/Dockerfile b/3.8/windows/windowsservercore-ltsc2016/Dockerfile
index 1f0d31544..9c511e650 100644
--- a/3.8/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.8/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.8.6
 ENV PYTHON_RELEASE 3.8.6
 
diff --git a/3.9/windows/windowsservercore-1809/Dockerfile b/3.9/windows/windowsservercore-1809/Dockerfile
index 1ba1ea8c9..f03a33b6e 100644
--- a/3.9/windows/windowsservercore-1809/Dockerfile
+++ b/3.9/windows/windowsservercore-1809/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.9.0
 ENV PYTHON_RELEASE 3.9.0
 
diff --git a/3.9/windows/windowsservercore-ltsc2016/Dockerfile b/3.9/windows/windowsservercore-ltsc2016/Dockerfile
index c2e83846f..5f60639b3 100644
--- a/3.9/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.9/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,6 +8,9 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION 3.9.0
 ENV PYTHON_RELEASE 3.9.0
 
diff --git a/Dockerfile-windowsservercore.template b/Dockerfile-windowsservercore.template
index d5ded28fb..040a6ed32 100644
--- a/Dockerfile-windowsservercore.template
+++ b/Dockerfile-windowsservercore.template
@@ -2,6 +2,9 @@ FROM mcr.microsoft.com/windows/servercore:%%PLACEHOLDER%%
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
 ENV PYTHON_VERSION %%PLACEHOLDER%%
 ENV PYTHON_RELEASE %%PLACEHOLDER%%