diff --git a/winbuild/build_prepare.py b/winbuild/build_prepare.py
index dfcbbb979..2dafb3d18 100644
--- a/winbuild/build_prepare.py
+++ b/winbuild/build_prepare.py
@@ -553,6 +553,7 @@ def build_pillow():
         cmd_cd("{pillow_dir}"),
         *prefs["header"],
         cmd_set("DISTUTILS_USE_SDK", "1"),  # use same compiler to build Pillow
+        cmd_set("py_vcruntime_redist", "true"),  # always use /MD, never /MT
         r'"{python_dir}\{python_exe}" setup.py build_ext --vendor-raqm --vendor-fribidi %*',  # noqa: E501
     ]