diff --git a/Misc/NEWS b/Misc/NEWS
index d9ff4fcd591..d657f2efa2d 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -328,6 +328,8 @@ Tests
 Build
 -----
 
+- Issue #27566: Fix clean target in freeze makefile (patch by Lisa Roach)
+
 - Issue #27705: Update message in validate_ucrtbase.py
 
 - Issue #27976: Deprecate building _ctypes with the bundled copy of libffi on
diff --git a/Tools/freeze/winmakemakefile.py b/Tools/freeze/winmakemakefile.py
index 439a1d7afa4..9bb3e6e1734 100644
--- a/Tools/freeze/winmakemakefile.py
+++ b/Tools/freeze/winmakemakefile.py
@@ -144,5 +144,5 @@ def realwork(vars, moddefns, target):
     print("<<")
     print()
     print("clean:")
-    print("\t-rm -f *.obj")
-    print("\t-rm -f $(target).exe")
+    print("\t-del /f *.obj")
+    print("\t-del /f $(target).exe")