diff --git a/template/Makefile.in b/template/Makefile.in
index 18f54c6f7d..e621ec0473 100644
--- a/template/Makefile.in
+++ b/template/Makefile.in
@@ -322,14 +322,14 @@ $(PROGRAM):
 
 $(PROGRAM): @XRUBY_LIBPATHENV_WRAPPER@
 
-PRE_LIBRUBY_UPDATE = [ -n "$(LIBRUBY_SO_UPDATE)" ] || $(gnumake:yes=exec) $(RM) $(LIBRUBY_EXTS)
+PRE_LIBRUBY_UPDATE = [ -z "$(EXTSTATIC)" -o -n "$(LIBRUBY_SO_UPDATE)" ] || $(gnumake:yes=exec) $(RM) $(LIBRUBY_EXTS)
 
 # We must `rm' the library each time this rule is invoked because "updating" a
 # MAB library on Apple/NeXT (see --enable-fat-binary in configure) is not
 # supported.
 $(LIBRUBY_A):
 		@$(RM) $@
-		@-[ -z "$(EXTSTATIC)" ] || $(PRE_LIBRUBY_UPDATE)
+		@-$(PRE_LIBRUBY_UPDATE)
 		$(ECHO) linking static-library $@
 		$(Q) $(AR) $(ARFLAGS) $@ $(LIBRUBY_A_OBJS) $(INITOBJS)
 		@-$(RANLIB) $@ 2> /dev/null || true
@@ -340,7 +340,7 @@ verify-static-library: $(LIBRUBY_A)
 		@$(RMALL) conftest$(EXEEXT) conftest.c conftest.dSYM
 
 $(LIBRUBY_SO):
-		@-[ -n "$(EXTSTATIC)" ] || $(PRE_LIBRUBY_UPDATE)
+		@-$(PRE_LIBRUBY_UPDATE)
 		$(ECHO) linking shared-library $@
 		$(Q) $(LDSHARED) $(DLDFLAGS) $(OBJS) $(DLDOBJS) $(SOLIBS) $(EXTSOLIBS) $(OUTFLAG)$@
 		-$(Q) $(OBJCOPY) -w -L '$(SYMBOL_PREFIX)Init_*' -L '$(SYMBOL_PREFIX)InitVM_*' \
diff --git a/win32/Makefile.sub b/win32/Makefile.sub
index 47837c42ad..cd0ba933da 100644
--- a/win32/Makefile.sub
+++ b/win32/Makefile.sub
@@ -1137,16 +1137,14 @@ $(STUBPROGRAM):	rubystub.$(OBJEXT) $(LIBRUBY) $(LIBRUBY_SO) $(RUBY_INSTALL_NAME)
 			$(OUTFLAG)$@ $(LIBRUBYARG) -link $(LDFLAGS) $(XLDFLAGS)
 !endif
 
-!if "$(LIBRUBY_SO_UPDATE)" == ""
+!if "$(EXTSTATIC)" != "" && "$(LIBRUBY_SO_UPDATE)" == ""
 PRE_LIBRUBY_UPDATE = $(RM) $(LIBRUBY_EXTS)
 !else
 PRE_LIBRUBY_UPDATE =
 !endif
 
 $(LIBRUBY_A):	$(OBJS) $(INITOBJS)
-!if "$(EXTSTATIC)" != ""
 		@-$(PRE_LIBRUBY_UPDATE)
-!endif
 		$(ECHO) linking static-library $(@:\=/)
 		$(Q) $(AR) $(ARFLAGS)$@ $(OBJS) $(INITOBJS)
 
@@ -1156,9 +1154,7 @@ $(LIBRUBY):	$(RUBYDEF)
 
 $(LIBRUBY_SO):	$(LIBRUBY_A) $(DLDOBJS) $(RUBYDEF) $(RUBY_SO_NAME).res
 		@echo $(DLDOBJS)
-!if "$(EXTSTATIC)" == ""
 		@-$(PRE_LIBRUBY_UPDATE)
-!endif
 		$(ECHO) linking shared-library $(@:\=/)
 		$(Q) $(LDSHARED) $(DLDOBJS) $(LIBRUBY_A) \
 			$(RUBY_SO_NAME).res $(SOLIBS) $(EXTSOLIBS) $(LIBS) \