diff --git a/deps/openssl/config/Makefile_VC-WIN32 b/deps/openssl/config/Makefile_VC-WIN32
index f7debe23833036..96610567469082 100644
--- a/deps/openssl/config/Makefile_VC-WIN32
+++ b/deps/openssl/config/Makefile_VC-WIN32
@@ -5678,8 +5678,10 @@ engines/padlock-dso-e_padlock.obj: engines/padlock-dso-e_padlock.d
 engines/padlock.def: util/engines.num  util/mkdef.pl
 	$(PERL) util/mkdef.pl --ordinals util/engines.num --name padlock --OS windows > engines/padlock.def
 
-distclean:
+clean:
+	$(RM) $(GENERATED_MANDATORY)
 	$(RM) $(GENERATED)
+distclean:
 	$(RM) configdata.pm
 	$(RM) makefile
 	$(RM) NUL
diff --git a/deps/openssl/config/Makefile_VC-WIN64-ARM b/deps/openssl/config/Makefile_VC-WIN64-ARM
index 9937bd5492a39b..03eaba0b078188 100644
--- a/deps/openssl/config/Makefile_VC-WIN64-ARM
+++ b/deps/openssl/config/Makefile_VC-WIN64-ARM
@@ -17,6 +17,7 @@ MINOR=1.1
 SHLIB_VERSION_NUMBER=1.1
 
 GENERATED_MANDATORY=crypto/include/internal/bn_conf.h crypto/include/internal/dso_conf.h include/openssl/opensslconf.h
+GENERATED=crypto/buildinf.h apps/progs.h
 
 INSTALL_LIBS="libcrypto.lib" "libssl.lib"
 INSTALL_SHLIBS="libcrypto-1_1-arm64.dll" "libssl-1_1-arm64.dll"
@@ -141,7 +142,9 @@ include/openssl/opensslconf.h:
 	"$(PERL)" "-I$(BLDDIR)" -Mconfigdata "util/dofile.pl" \
 	    "-omakefile" "include/openssl/opensslconf.h.in" > $@
 
-distclean:
+clean:
+	$(RM) $(GENERATED_MANDATORY)
 	$(RM) $(GENERATED)
+distclean:
 	$(RM) /Q /F configdata.pm
 	$(RM) /Q /F makefile
diff --git a/deps/openssl/config/Makefile_VC-WIN64A b/deps/openssl/config/Makefile_VC-WIN64A
index fa66acfd517dfb..3e4adce958e409 100644
--- a/deps/openssl/config/Makefile_VC-WIN64A
+++ b/deps/openssl/config/Makefile_VC-WIN64A
@@ -2950,7 +2950,9 @@ engines/e_padlock.d: "engines/e_padlock.c"
 engines/e_padlock.obj: engines/e_padlock.d
 	$(CC)  $(DSO_CFLAGS) /I "include" $(DSO_CPPFLAGS) -c $(COUTFLAG)$@ "engines/e_padlock.c"
 
-distclean:
+clean:
+	$(RM) $(GENERATED_MANDATORY)
 	$(RM) $(GENERATED)
+distclean:
 	$(RM) /Q /F configdata.pm
 	$(RM) /Q /F makefile
diff --git a/deps/openssl/config/generate_gypi.pl b/deps/openssl/config/generate_gypi.pl
index 891ccb62bbf6d4..978ddbb3b3504a 100755
--- a/deps/openssl/config/generate_gypi.pl
+++ b/deps/openssl/config/generate_gypi.pl
@@ -46,7 +46,7 @@
 # Generate arch dependent header files with Makefile
 my $buildinf = "crypto/buildinf.h";
 my $progs = "apps/progs.h";
-my $cmd1 = "cd ../openssl; make -f $makefile build_generated $buildinf $progs;";
+my $cmd1 = "cd ../openssl; make -f $makefile clean build_generated $buildinf $progs;";
 system($cmd1) == 0 or die "Error in system($cmd1)";
 
 # Copy and move all arch dependent header files into config/archs