diff --git a/Makefile.pre.in b/Makefile.pre.in
index d30e565dd49..3e56e422d78 100644
--- a/Makefile.pre.in
+++ b/Makefile.pre.in
@@ -221,7 +221,6 @@ LIBOBJS=	@LIBOBJS@
 PYTHON=		python$(EXE)
 BUILDPYTHON=	python$(BUILDEXE)
 
-cross_compiling=@cross_compiling@
 PYTHON_FOR_GEN=@PYTHON_FOR_GEN@
 PYTHON_FOR_BUILD=@PYTHON_FOR_BUILD@
 _PYTHON_HOST_PLATFORM=@_PYTHON_HOST_PLATFORM@
@@ -719,17 +718,13 @@ Programs/_freeze_importlib.o: Programs/_freeze_importlib.c Makefile
 Programs/_freeze_importlib: Programs/_freeze_importlib.o $(LIBRARY_OBJS_OMIT_FROZEN)
 	$(LINKCC) $(PY_LDFLAGS) -o $@ Programs/_freeze_importlib.o $(LIBRARY_OBJS_OMIT_FROZEN) $(LIBS) $(MODLIBS) $(SYSLIBS) $(LDLAST)
 
-Python/importlib_external.h: $(srcdir)/Lib/importlib/_bootstrap_external.py Programs/_freeze_importlib
-	if test "$(cross_compiling)" != "yes"; then \
-	    ./Programs/_freeze_importlib \
-	        $(srcdir)/Lib/importlib/_bootstrap_external.py Python/importlib_external.h; \
-	fi
+Python/importlib_external.h: @GENERATED_COMMENT@ $(srcdir)/Lib/importlib/_bootstrap_external.py Programs/_freeze_importlib
+	./Programs/_freeze_importlib \
+	    $(srcdir)/Lib/importlib/_bootstrap_external.py Python/importlib_external.h
 
-Python/importlib.h: $(srcdir)/Lib/importlib/_bootstrap.py Programs/_freeze_importlib
-	if test "$(cross_compiling)" != "yes"; then \
-	    ./Programs/_freeze_importlib \
-	        $(srcdir)/Lib/importlib/_bootstrap.py Python/importlib.h; \
-	fi
+Python/importlib.h: @GENERATED_COMMENT@ $(srcdir)/Lib/importlib/_bootstrap.py Programs/_freeze_importlib
+	./Programs/_freeze_importlib \
+	    $(srcdir)/Lib/importlib/_bootstrap.py Python/importlib.h
 
 
 ############################################################################
@@ -789,22 +784,11 @@ Python/sysmodule.o: $(srcdir)/Python/sysmodule.c Makefile
 
 $(IO_OBJS): $(IO_H)
 
-$(GRAMMAR_H): $(GRAMMAR_INPUT) @PGEN_DEPENDENCY@
+$(GRAMMAR_H): @GENERATED_COMMENT@ $(GRAMMAR_INPUT) $(PGEN)
 	@$(MKDIR_P) Include
-	# Avoid copying the file onto itself for an in-tree build
-	if test "$(cross_compiling)" != "yes"; then \
-		$(PGEN) $(GRAMMAR_INPUT) $(GRAMMAR_H) $(GRAMMAR_C); \
-	else \
-		cp $(srcdir)/Include/graminit.h $(GRAMMAR_H).tmp; \
-		mv $(GRAMMAR_H).tmp $(GRAMMAR_H); \
-	fi
-$(GRAMMAR_C): $(GRAMMAR_H)
-	if test "$(cross_compiling)" != "yes"; then \
-		touch $(GRAMMAR_C); \
-	else \
-		cp $(srcdir)/Python/graminit.c $(GRAMMAR_C).tmp; \
-		mv $(GRAMMAR_C).tmp $(GRAMMAR_C); \
-	fi
+	$(PGEN) $(GRAMMAR_INPUT) $(GRAMMAR_H) $(GRAMMAR_C)
+$(GRAMMAR_C): @GENERATED_COMMENT@ $(GRAMMAR_H)
+	touch $(GRAMMAR_C)
 
 $(PGEN): $(PGENOBJS)
 		$(CC) $(OPT) $(PY_LDFLAGS) $(PGENOBJS) $(LIBS) -o $(PGEN)
diff --git a/Misc/NEWS b/Misc/NEWS
index ffd647113e4..fe81bbd7cbb 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -154,8 +154,9 @@ Build
 - Issue #27453: CPP invocation in configure must use CPPFLAGS. Patch by
   Chi Hsuan Yen.
 
-- Issue #27490: Do not build pgen when cross-compiling.  Patch by Thomas
-  Perl.
+- Issue #27641: The configure script now inserts comments into the makefile
+  to prevent the pgen and _freeze_importlib executables from being cross-
+  compiled.
 
 - Issue #26662: Set PYTHON_FOR_GEN in configure as the Python program to be
   used for file generation during the build.
diff --git a/configure b/configure
index bb89a5a059b..26837342a48 100755
--- a/configure
+++ b/configure
@@ -739,7 +739,7 @@ UNIVERSALSDK
 CONFIG_ARGS
 SOVERSION
 VERSION
-PGEN_DEPENDENCY
+GENERATED_COMMENT
 PYTHON_FOR_BUILD
 PYTHON_FOR_GEN
 host_os
@@ -750,7 +750,6 @@ build_os
 build_vendor
 build_cpu
 build
-cross_compiling
 HAS_HG
 HGBRANCH
 HGTAG
@@ -2875,7 +2874,6 @@ fi
 ac_config_headers="$ac_config_headers pyconfig.h"
 
 
-
 ac_aux_dir=
 for ac_dir in "$srcdir" "$srcdir/.." "$srcdir/../.."; do
   if test -f "$ac_dir/install-sh"; then
@@ -3050,12 +3048,13 @@ $as_echo_n "checking for python interpreter for cross build... " >&6; }
 $as_echo "$interp" >&6; }
 	PYTHON_FOR_BUILD='_PYTHON_PROJECT_BASE=$(abs_builddir) _PYTHON_HOST_PLATFORM=$(_PYTHON_HOST_PLATFORM) PYTHONPATH=$(shell test -f pybuilddir.txt && echo $(abs_builddir)/`cat pybuilddir.txt`:)$(srcdir)/Lib:$(srcdir)/Lib/$(PLATDIR) '$interp
     fi
-    PGEN_DEPENDENCY=''
+    # Used to comment out stuff for rebuilding generated files
+    GENERATED_COMMENT='#'
 elif test "$cross_compiling" = maybe; then
     as_fn_error $? "Cross compiling required --host=HOST-TUPLE and --build=ARCH" "$LINENO" 5
 else
     PYTHON_FOR_BUILD='./$(BUILDPYTHON) -E'
-    PGEN_DEPENDENCY='$(PGEN)'
+    GENERATED_COMMENT=''
 fi
 
 
diff --git a/configure.ac b/configure.ac
index 8135c716f3c..5312c2b3156 100644
--- a/configure.ac
+++ b/configure.ac
@@ -49,7 +49,6 @@ fi
 AC_CONFIG_SRCDIR([Include/object.h])
 AC_CONFIG_HEADER(pyconfig.h)
 
-AC_SUBST(cross_compiling)
 AC_CANONICAL_HOST
 AC_SUBST(build)
 AC_SUBST(host)
@@ -81,15 +80,16 @@ if test "$cross_compiling" = yes; then
         AC_MSG_RESULT($interp)
 	PYTHON_FOR_BUILD='_PYTHON_PROJECT_BASE=$(abs_builddir) _PYTHON_HOST_PLATFORM=$(_PYTHON_HOST_PLATFORM) PYTHONPATH=$(shell test -f pybuilddir.txt && echo $(abs_builddir)/`cat pybuilddir.txt`:)$(srcdir)/Lib:$(srcdir)/Lib/$(PLATDIR) '$interp
     fi
-    PGEN_DEPENDENCY=''
+    # Used to comment out stuff for rebuilding generated files
+    GENERATED_COMMENT='#'
 elif test "$cross_compiling" = maybe; then
     AC_MSG_ERROR([Cross compiling required --host=HOST-TUPLE and --build=ARCH])
 else
     PYTHON_FOR_BUILD='./$(BUILDPYTHON) -E'
-    PGEN_DEPENDENCY='$(PGEN)'
+    GENERATED_COMMENT=''
 fi
 AC_SUBST(PYTHON_FOR_BUILD)
-AC_SUBST(PGEN_DEPENDENCY)
+AC_SUBST(GENERATED_COMMENT)
 
 dnl Ensure that if prefix is specified, it does not end in a slash. If
 dnl it does, we get path names containing '//' which is both ugly and