diff --git a/.github/actions/setup/baseruby/action.yml b/.github/actions/setup/baseruby/action.yml
index 76fe068897a163..9c93be0f9a9a82 100644
--- a/.github/actions/setup/baseruby/action.yml
+++ b/.github/actions/setup/baseruby/action.yml
@@ -45,7 +45,7 @@ runs:
         ln -sr "$srcdir" "$builddir/.src"
         pushd "$builddir"
         .src/configure "--prefix=${installdir}" --disable-install-doc
-        CONFIGURE_ARGS=--with-out-ext=-test- make install
+        CONFIGURE_ARGS=--with-out-ext=-test- make install dump_ast
         install dump_ast "${installdir}/bin"
         {
           echo "${installdir}/bin/dump_ast"
diff --git a/.github/actions/setup/directories/action.yml b/.github/actions/setup/directories/action.yml
index 78b57c17619a51..bb1c92bd735168 100644
--- a/.github/actions/setup/directories/action.yml
+++ b/.github/actions/setup/directories/action.yml
@@ -157,11 +157,13 @@ runs:
       shell: bash
       working-directory: ${{ inputs.srcdir }}
       run: |
+        ruby tool/missing-baseruby.bat --verbose
         touch config.status .rbconfig.time
         for mk in Makefile GNUmakefile; do
           sed -f tool/prereq.status template/$mk.in > $mk
         done
         make up
+        echo RUBY_DUMP_AST=true >> "$GITHUB_ENV"
 
     # Cleanup, runs even on failure
     - if: always() && inputs.makeup
diff --git a/.github/workflows/annocheck.yml b/.github/workflows/annocheck.yml
index f58363f76a23e6..1fda0b98877b3b 100644
--- a/.github/workflows/annocheck.yml
+++ b/.github/workflows/annocheck.yml
@@ -67,17 +67,17 @@ jobs:
           sparse-checkout: /.github
           persist-credentials: false
 
+      - uses: ruby/setup-ruby@003a5c4d8d6321bd302e38f6f0ec593f77f06600 # v1.319.0
+        with:
+          ruby-version: '3.1'
+          bundler: none
+
       - uses: ./.github/actions/setup/directories
         with:
           srcdir: src
           builddir: build
           makeup: true
 
-      - uses: ruby/setup-ruby@003a5c4d8d6321bd302e38f6f0ec593f77f06600 # v1.319.0
-        with:
-          ruby-version: '3.1'
-          bundler: none
-
       # Minimal flags to pass the check.
       # -g0 disables backtraces when SEGV.  Do not set that.
       - name: Run configure
diff --git a/configure.ac b/configure.ac
index f636d19e3f1026..6fbbb11178d219 100644
--- a/configure.ac
+++ b/configure.ac
@@ -119,12 +119,16 @@ AC_SUBST(X_BUILD_EXEEXT)
 AC_ARG_WITH(dump-ast,
 	AS_HELP_STRING([--with-dump-ast=DUMP_AST], [use DUMP_AST as dump_ast; for cross-compiling with a host-built dump_ast]),
 	[DUMP_AST=$withval DUMP_AST_TARGET='$(empty)'],
-	[AS_IF([test "$cross_compiling" = yes], [
+	[AS_IF([test ${RUBY_DUMP_AST+set}], [
+	    DUMP_AST="${RUBY_DUMP_AST}"
+	    DUMP_AST_TARGET='$(empty)'
+	], [test "$cross_compiling" = yes], [
 	    DUMP_AST='build-tool/dump_ast$(BUILD_EXEEXT)'
+	    DUMP_AST_TARGET='$(DUMP_AST)'
 	], [
 	    DUMP_AST='./dump_ast$(BUILD_EXEEXT)'
-	])
-	DUMP_AST_TARGET='$(DUMP_AST)'])
+	    DUMP_AST_TARGET='$(DUMP_AST)'
+	])])
 dnl Without baseruby, .rbinc files cannot be regenerated, so clear the
 dnl dependency on dump_ast to avoid rebuilding pre-generated .rbinc files.
 AS_IF([test "$HAVE_BASERUBY" = no], [DUMP_AST_TARGET='$(empty)'])
diff --git a/win32/Makefile.sub b/win32/Makefile.sub
index 203179006f8951..4f95c10bcb5690 100644
--- a/win32/Makefile.sub
+++ b/win32/Makefile.sub
@@ -567,6 +567,12 @@ ABI_VERSION_HDR = $(hdrdir)/ruby/internal/abi.h
 
 !if defined(DUMP_AST)
 DUMP_AST_TARGET = $(empty)
+!else if defined(RUBY_DUMP_AST)
+DUMP_AST = $(RUBY_DUMP_AST)
+DUMP_AST_TARGET = $(empty)
+!else if "$(CROSS_COMPILING)" == "yes"
+DUMP_AST = ruby-dump_ast$(BUILD_EXEEXT)
+DUMP_AST_TARGET = $(DUMP_AST)
 !else
 DUMP_AST = dump_ast$(BUILD_EXEEXT)
 DUMP_AST_TARGET = $(DUMP_AST)