diff --git a/.github/actions/slack/action.yml b/.github/actions/slack/action.yml
index 4a398da1d1dab3..6f89bef11ae061 100644
--- a/.github/actions/slack/action.yml
+++ b/.github/actions/slack/action.yml
@@ -35,7 +35,7 @@ runs:
   using: composite
 
   steps:
-    - uses: ruby/action-slack@54175162371f1f7c8eb94d7c8644ee2479fcd375 # v3.2.2
+    - uses: ruby/action-slack@d260b61aa817726d5bedd22dd6cc305787fa4cdd # v4.0.0
       with:
         payload: |
           {
diff --git a/.github/workflows/annocheck.yml b/.github/workflows/annocheck.yml
index c8b922d1978849..f2454ca9788455 100644
--- a/.github/workflows/annocheck.yml
+++ b/.github/workflows/annocheck.yml
@@ -73,7 +73,7 @@ jobs:
           builddir: build
           makeup: true
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
diff --git a/.github/workflows/auto_review_pr.yml b/.github/workflows/auto_review_pr.yml
index 83338337ef65a2..90323e620addc9 100644
--- a/.github/workflows/auto_review_pr.yml
+++ b/.github/workflows/auto_review_pr.yml
@@ -29,7 +29,7 @@ jobs:
         with:
           persist-credentials: false
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.4'
           bundler: none
diff --git a/.github/workflows/baseruby.yml b/.github/workflows/baseruby.yml
index bac0a298b70a2c..7f5a090a19a451 100644
--- a/.github/workflows/baseruby.yml
+++ b/.github/workflows/baseruby.yml
@@ -48,7 +48,7 @@ jobs:
           - ruby-3.3
 
     steps:
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: ${{ matrix.ruby }}
           bundler: none
diff --git a/.github/workflows/bundled_gems.yml b/.github/workflows/bundled_gems.yml
index 67113f422a7578..5a7b30fc3d8983 100644
--- a/.github/workflows/bundled_gems.yml
+++ b/.github/workflows/bundled_gems.yml
@@ -38,7 +38,7 @@ jobs:
         with:
           token: ${{ (github.repository == 'ruby/ruby' && !startsWith(github.event_name, 'pull')) && secrets.MATZBOT_AUTO_UPDATE_TOKEN || secrets.GITHUB_TOKEN }}
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: 4.0
 
diff --git a/.github/workflows/check_dependencies.yml b/.github/workflows/check_dependencies.yml
index 7fec25c2a362a4..455c3c6b67df77 100644
--- a/.github/workflows/check_dependencies.yml
+++ b/.github/workflows/check_dependencies.yml
@@ -42,7 +42,7 @@ jobs:
 
       - uses: ./.github/actions/setup/directories
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
diff --git a/.github/workflows/check_misc.yml b/.github/workflows/check_misc.yml
index 518e461ab46b14..71bccdb5c9e2ad 100644
--- a/.github/workflows/check_misc.yml
+++ b/.github/workflows/check_misc.yml
@@ -23,7 +23,7 @@ jobs:
           token: ${{ (github.repository == 'ruby/ruby' && !startsWith(github.event_name, 'pull')) && secrets.MATZBOT_AUTO_UPDATE_TOKEN || secrets.GITHUB_TOKEN }}
           persist-credentials: false
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: head
 
diff --git a/.github/workflows/check_sast.yml b/.github/workflows/check_sast.yml
index 136fbc7619d88b..c80d4a57fae6cb 100644
--- a/.github/workflows/check_sast.yml
+++ b/.github/workflows/check_sast.yml
@@ -78,14 +78,14 @@ jobs:
           persist-credentials: false
 
       - name: Initialize CodeQL
-        uses: github/codeql-action/init@e46ed2cbd01164d986452f91f178727624ae40d7 # v4.35.3
+        uses: github/codeql-action/init@68bde559dea0fdcac2102bfdf6230c5f70eb485e # v4.35.4
         with:
           languages: ${{ matrix.language }}
           build-mode: none
           config-file: .github/codeql/codeql-config.yml
 
       - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@e46ed2cbd01164d986452f91f178727624ae40d7 # v4.35.3
+        uses: github/codeql-action/analyze@68bde559dea0fdcac2102bfdf6230c5f70eb485e # v4.35.4
         with:
           category: '/language:${{ matrix.language }}'
           upload: False
@@ -126,7 +126,7 @@ jobs:
         continue-on-error: true
 
       - name: Upload SARIF
-        uses: github/codeql-action/upload-sarif@e46ed2cbd01164d986452f91f178727624ae40d7 # v4.35.3
+        uses: github/codeql-action/upload-sarif@68bde559dea0fdcac2102bfdf6230c5f70eb485e # v4.35.4
         with:
           sarif_file: sarif-results/${{ matrix.language }}.sarif
         continue-on-error: true
diff --git a/.github/workflows/modgc.yml b/.github/workflows/modgc.yml
index 319841b51e8e2d..8eea71764b851c 100644
--- a/.github/workflows/modgc.yml
+++ b/.github/workflows/modgc.yml
@@ -62,7 +62,7 @@ jobs:
         uses: ./.github/actions/setup/ubuntu
         if: ${{ contains(matrix.os, 'ubuntu') }}
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
@@ -105,7 +105,7 @@ jobs:
           ${SETARCH} ../src/configure -C --disable-install-doc --with-modular-gc="${MODULAR_GC_DIR}" \
           ${arch:+--target=$arch-$OSTYPE --host=$arch-$OSTYPE}
 
-      - uses: actions-rust-lang/setup-rust-toolchain@2b1f5e9b395427c92ee4e3331786ca3c37afe2d7 # v1.16.0
+      - uses: actions-rust-lang/setup-rust-toolchain@46268bd060767258de96ed93c1251119784f2ab6 # v1.16.1
       - name: Set MMTk environment variables
         run: |
           echo 'EXCLUDES=../src/test/.excludes-mmtk' >> $GITHUB_ENV
diff --git a/.github/workflows/parse_y.yml b/.github/workflows/parse_y.yml
index 3ba87c684daa26..4fca3706a590cd 100644
--- a/.github/workflows/parse_y.yml
+++ b/.github/workflows/parse_y.yml
@@ -59,7 +59,7 @@ jobs:
 
       - uses: ./.github/actions/setup/ubuntu
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
diff --git a/.github/workflows/publish.yml b/.github/workflows/publish.yml
index 1b3df3a6eabd3e..6f9332b1def804 100644
--- a/.github/workflows/publish.yml
+++ b/.github/workflows/publish.yml
@@ -22,7 +22,7 @@ jobs:
         with:
           persist-credentials: false
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: 3.3.4
 
diff --git a/.github/workflows/scorecards.yml b/.github/workflows/scorecards.yml
index a74c4787159c03..4160ee07f8f484 100644
--- a/.github/workflows/scorecards.yml
+++ b/.github/workflows/scorecards.yml
@@ -73,6 +73,6 @@ jobs:
       # Upload the results to GitHub's code scanning dashboard (optional).
       # Commenting out will disable upload of results to your repo's Code Scanning dashboard
       - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@e46ed2cbd01164d986452f91f178727624ae40d7 # v4.35.3
+        uses: github/codeql-action/upload-sarif@68bde559dea0fdcac2102bfdf6230c5f70eb485e # v4.35.4
         with:
           sarif_file: results.sarif
diff --git a/.github/workflows/spec_guards.yml b/.github/workflows/spec_guards.yml
index 3836ae30aa3557..ce4a055fac5370 100644
--- a/.github/workflows/spec_guards.yml
+++ b/.github/workflows/spec_guards.yml
@@ -49,7 +49,7 @@ jobs:
         with:
           persist-credentials: false
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: ${{ matrix.ruby }}
           bundler: none
diff --git a/.github/workflows/sync_default_gems.yml b/.github/workflows/sync_default_gems.yml
index f867919348a0e1..d06b52e22e2729 100644
--- a/.github/workflows/sync_default_gems.yml
+++ b/.github/workflows/sync_default_gems.yml
@@ -39,7 +39,7 @@ jobs:
         with:
           token: ${{ github.repository == 'ruby/ruby' && secrets.MATZBOT_AUTO_UPDATE_TOKEN || secrets.GITHUB_TOKEN }}
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.4'
           bundler: none
diff --git a/.github/workflows/ubuntu.yml b/.github/workflows/ubuntu.yml
index cff80e47c7ef28..4995680930029b 100644
--- a/.github/workflows/ubuntu.yml
+++ b/.github/workflows/ubuntu.yml
@@ -70,7 +70,7 @@ jobs:
         with:
           arch: ${{ matrix.arch }}
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
diff --git a/.github/workflows/wasm.yml b/.github/workflows/wasm.yml
index 61f7df0c179a7b..0d1fb61cc376dc 100644
--- a/.github/workflows/wasm.yml
+++ b/.github/workflows/wasm.yml
@@ -65,6 +65,11 @@ jobs:
           sparse-checkout: /.github
           persist-credentials: false
 
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
+        with:
+          ruby-version: '3.1'
+          bundler: none
+
       - uses: ./.github/actions/setup/directories
         with:
           srcdir: src
@@ -99,16 +104,14 @@ jobs:
         run: |
           echo "WASI_SDK_PATH=/opt/wasi-sdk" >> $GITHUB_ENV
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
-        with:
-          ruby-version: '3.1'
-          bundler: none
-
       - name: Build baseruby
+        id: baseruby
         run: |
           set -ex
           mkdir ../baseruby
           pushd ../baseruby
+          echo "ruby=$PWD/install/bin/ruby" >> $GITHUB_OUTPUT
+          echo "dump_ast=$PWD/dump_ast" >> $GITHUB_OUTPUT
           ../src/configure --prefix=$PWD/install
           make
           make install
@@ -120,20 +123,38 @@ jobs:
         working-directory: src
 
       - name: Run configure
-        run: |
-          ../src/configure \
-            --host wasm32-unknown-wasi \
-            --with-baseruby=$PWD/../baseruby/install/bin/ruby \
-            --with-dump-ast=$PWD/../baseruby/dump_ast \
-            --with-static-linked-ext \
-            --with-ext=cgi/escape,continuation,coverage,date,digest/bubblebabble,digest,digest/md5,digest/rmd160,digest/sha1,digest/sha2,etc,fcntl,json,json/generator,json/parser,objspace,pathname,rbconfig/sizeof,ripper,stringio,strscan,monitor \
-            LDFLAGS=" \
-              -Xlinker --stack-first \
-              -Xlinker -z -Xlinker stack-size=16777216 \
-            " \
-            optflags="${{ matrix.entry.optflags }}" \
-            debugflags="${{ matrix.entry.debugflags }}" \
-            wasmoptflags="${{ matrix.entry.wasmoptflags }} ${{ matrix.entry.debugflags }}"
+        run: >-
+          ../src/configure
+          --host wasm32-unknown-wasi
+          --with-baseruby="${{ steps.baseruby.outputs.ruby }}"
+          --with-dump-ast="${{ steps.baseruby.outputs.dump_ast }}"
+          --with-static-linked-ext
+          --with-ext=${EXTS// /,}
+          LDFLAGS="
+          -Xlinker --stack-first
+          -Xlinker -z -Xlinker stack-size=16777216
+          "
+          optflags="${{ matrix.entry.optflags }}"
+          debugflags="${{ matrix.entry.debugflags }}"
+          wasmoptflags="${{ matrix.entry.wasmoptflags }} ${{ matrix.entry.debugflags }}"
+        env:
+          EXTS:
+            cgi/escape
+            continuation
+            coverage
+            date
+            digest
+            digest/*
+            erb/escape
+            etc
+            fcntl
+            json
+            json/*
+            objspace
+            rbconfig/sizeof
+            ripper
+            stringio
+            strscan
 
       # miniruby may not be built when cross-compling
       - run: make mini ruby
diff --git a/.github/workflows/windows.yml b/.github/workflows/windows.yml
index caf38bb2bff406..d2c8feac988e7c 100644
--- a/.github/workflows/windows.yml
+++ b/.github/workflows/windows.yml
@@ -26,17 +26,16 @@ jobs:
       matrix:
         include:
           - os: 2022
-            vc: 2022
             test_task: check
-          - os: 2025
-            vc: 2022
+          - os: 2022
+            test_task: test-bundled-gems
+          - os: 2025-vs2026
             test_task: check
+          - os: 2025-vs2026
+            test_task: test-bundled-gems
           - os: 11-arm
             test_task: 'btest test-basic test-tool' # check and test-spec are broken yet.
             target: arm64
-          - os: 2025
-            vc: 2022
-            test_task: test-bundled-gems
       fail-fast: false
 
     runs-on: windows-${{ matrix.os }}
@@ -49,7 +48,7 @@ jobs:
       || (github.event.pull_request.user.login == 'dependabot[bot]' && !startsWith(github.head_ref, 'dependabot/vcpkg'))
       )}}
 
-    name: Windows ${{ matrix.os }}/Visual C++ ${{ matrix.vc }} (${{ matrix.test_task }})
+    name: Windows ${{ matrix.os }} (${{ matrix.test_task }})
 
     env:
       GITPULLOPTIONS: --no-tags origin ${{ github.ref }}
@@ -59,7 +58,7 @@ jobs:
       - run: md build
         working-directory:
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           # windows-11-arm has only 3.4.1, 3.4.2, 3.4.3, head
           ruby-version: ${{ !endsWith(matrix.os, 'arm') && '3.1' || '3.4' }}
@@ -113,8 +112,6 @@ jobs:
         # %TEMP% is inconsistent with %TMP% and test-all expects they are consistent.
         # https://github.com/actions/virtual-environments/issues/712#issuecomment-613004302
         run: |
-          ::- Set up VC ${{ matrix.vc }}
-
           ::- Using sort.exe located in the same directory as comm.exe
           ::- should probably work just fine.
           for %%I in (comm.exe) do set "sort=%%~dp$PATH:I\sort.exe"
@@ -188,14 +185,14 @@ jobs:
 
       - uses: ./.github/actions/slack
         with:
-          label: Windows ${{ matrix.os }} / VC ${{ matrix.vc }} / ${{ matrix.test_task || 'check' }}
+          label: Windows ${{ matrix.os }} / ${{ matrix.test_task || 'check' }}
           SLACK_WEBHOOK_URL: ${{ secrets.SIMPLER_ALERTS_URL }} # ruby-lang slack: ruby/simpler-alerts-bot
         if: ${{ failure() }}
 
   result:
     if: ${{ always() }}
     name: ${{ github.workflow }} result
-    runs-on: windows-latest
+    runs-on: windows-2025-vs2026
     needs: [make]
     steps:
       - run: exit 1
diff --git a/.github/workflows/wsl.yml b/.github/workflows/wsl.yml
index 189f978e299d3e..470b68fe663b9c 100644
--- a/.github/workflows/wsl.yml
+++ b/.github/workflows/wsl.yml
@@ -19,7 +19,7 @@ permissions:
 
 jobs:
   wsl:
-    runs-on: windows-2025
+    runs-on: windows-2025-vs2026
 
     if: >-
       ${{!(false
diff --git a/.github/workflows/yjit-ubuntu.yml b/.github/workflows/yjit-ubuntu.yml
index 5b320b3fa9bb94..cbb002f42e9193 100644
--- a/.github/workflows/yjit-ubuntu.yml
+++ b/.github/workflows/yjit-ubuntu.yml
@@ -133,7 +133,7 @@ jobs:
 
       - uses: ./.github/actions/setup/ubuntu
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
diff --git a/.github/workflows/zjit-macos.yml b/.github/workflows/zjit-macos.yml
index 1e57379e678fc0..18b6e9b38f8ca2 100644
--- a/.github/workflows/zjit-macos.yml
+++ b/.github/workflows/zjit-macos.yml
@@ -93,7 +93,7 @@ jobs:
           rustup install ${{ matrix.rust_version }} --profile minimal
           rustup default ${{ matrix.rust_version }}
 
-      - uses: taiki-e/install-action@cca35edeb1d01366c2843b68fc3ca441446d73d3 # v2.77.1
+      - uses: taiki-e/install-action@3235f8901fd37ffed0052b276cec25a362fb82e9 # v2.77.7
         with:
           tool: nextest@0.9
         if: ${{ matrix.test_task == 'zjit-check' }}
diff --git a/.github/workflows/zjit-ubuntu.yml b/.github/workflows/zjit-ubuntu.yml
index 633628f3e6ec08..5b4420d2452501 100644
--- a/.github/workflows/zjit-ubuntu.yml
+++ b/.github/workflows/zjit-ubuntu.yml
@@ -114,12 +114,12 @@ jobs:
 
       - uses: ./.github/actions/setup/ubuntu
 
-      - uses: ruby/setup-ruby@c4e5b1316158f92e3d49443a9d58b31d25ac0f8f # v1.306.0
+      - uses: ruby/setup-ruby@6aaa311d81eba98ae12eaffbcb63296ace0efcde # v1.307.0
         with:
           ruby-version: '3.1'
           bundler: none
 
-      - uses: taiki-e/install-action@cca35edeb1d01366c2843b68fc3ca441446d73d3 # v2.77.1
+      - uses: taiki-e/install-action@3235f8901fd37ffed0052b276cec25a362fb82e9 # v2.77.7
         with:
           tool: nextest@0.9
         if: ${{ matrix.test_task == 'zjit-check' }}
diff --git a/common.mk b/common.mk
index 4407bc41fddec5..b1debdebc9730b 100644
--- a/common.mk
+++ b/common.mk
@@ -69,7 +69,9 @@ LIBRUBY_EXTS  = ./.libruby-with-ext.time
 REVISION_H    = ./.revision.time
 PLATFORM_D    = $(TIMESTAMPDIR)/.$(PLATFORM_DIR).time
 ENC_TRANS_D   = $(TIMESTAMPDIR)/.enc-trans.time
-RDOC          = $(XRUBY) "$(tooldir)/rdoc-srcdir"
+X_$(no_baseruby:no=NO_)BASERUBY = $(BASERUBY)
+X_$(yes_baseruby:yes=NO_)BASERUBY = $(XRUBY)
+RDOC          = $(X_BASERUBY) --enable-gems "$(tooldir)/rdoc-srcdir"
 RDOCOUT       = $(EXTOUT)/rdoc
 HTMLOUT       = $(EXTOUT)/html
 CAPIOUT       = doc/capi
@@ -344,7 +346,7 @@ $(EXTS_MK): ext/configure-ext.mk $(srcdir)/template/exts.mk.tmpl \
 	    $(srcdir)/template/exts.mk.tmpl --gnumake=$(gnumake) --configure-exts=ext/configure-ext.mk
 
 ext/configure-ext.mk: $(PREP) all-incs $(MKFILES) $(RBCONFIG) $(LIBRUBY) \
-		$(srcdir)/template/configure-ext.mk.tmpl
+		$(srcdir)/template/configure-ext.mk.tmpl update-default-gemspecs
 	$(ECHO) generating makefiles $@
 	$(Q)$(MAKEDIRS) $(@D)
 	$(Q)$(MINIRUBY) $(tooldir)/generic_erb.rb -o $@ -c \
@@ -623,11 +625,11 @@ post-install-dbg::
 srcs-doc: prepare-gems
 
 RDOC_DEPENDS = main srcs-doc
-rdoc: PHONY $(RDOC_DEPENDS) $(RBCONFIG)
+rdoc: PHONY $(RDOC_DEPENDS) $(RBCONFIG) update-default-gemspecs
 	@echo Generating RDoc documentation
 	$(Q) $(RDOC) --ri --op "$(RDOCOUT)" $(RDOC_GEN_OPTS) $(RDOCFLAGS) .
 
-html: PHONY $(RDOC_DEPENDS) $(RBCONFIG)
+html: PHONY $(RDOC_DEPENDS) $(RBCONFIG) update-default-gemspecs
 	@echo Generating RDoc HTML files
 	$(Q) $(RDOC) --op "$(HTMLOUT)" $(RDOC_GEN_OPTS) $(RDOCFLAGS) .
 
@@ -1485,7 +1487,7 @@ dist:
 up:: update-remote
 
 up$(DOT_WAIT)::
-	-$(Q)$(MAKE) $(mflags) Q=$(Q) REVISION_FORCE=PHONY ALWAYS_UPDATE_UNICODE= after-update
+	-$(Q)$(MAKE) $(mflags) Q=$(Q) REVISION_FORCE=PHONY ALWAYS_UPDATE_UNICODE= MINIRUBY=$(BASERUBY) after-update
 
 yes::
 no::
@@ -1494,6 +1496,7 @@ after-update:: common-srcs
 after-update:: $(REVISION_H)
 after-update:: extract-extlibs
 after-update:: extract-gems
+after-update:: update-default-gemspecs
 
 update-src::
 	$(Q) $(RM) $(REVISION_H) revision.h "$(srcdir)/$(REVISION_H)" "$(srcdir)/revision.h"
@@ -1576,31 +1579,13 @@ test-bundled-gems-precheck: $(TEST_RUNNABLE)-test-bundled-gems-precheck
 yes-test-bundled-gems-precheck: $(PRECHECK_BUNDLED_GEMS:yes=main)
 no-test-bundled-gems-precheck:
 
-update-default-gemspecs: $(TEST_RUNNABLE)-update-default-gemspecs
-no-update-default-gemspecs:
-yes-update-default-gemspecs: $(PRECHECK_BUNDLED_GEMS:yes=main) $(PROGRAM)
+yes-update-default-gemspecs no-update-default-gemspecs: update-default-gemspecs
+update-default-gemspecs: $(PREP)
 	@$(MAKEDIRS) $(srcdir)/.bundle/specifications
-	@$(XRUBY) -W0 -C "$(srcdir)" -rrubygems \
-	    -e "destdir = ARGV.shift" \
-	    -e "ARGV.each do |basedir|" \
-	    -e   "Dir.glob(basedir+'/**/*.gemspec') do |g|" \
-	    -e     "dir, base = File.split(g)" \
-	    -e     "spec = Dir.chdir(dir) {Gem::Specification.load(base)} ||" \
-	    -e         "Gem::Specification.load(g)" \
-	    -e     "unless spec" \
-	    -e       "puts %[Ignoring #{g}]" \
-	    -e       "next" \
-	    -e     "end" \
-	    -e     "spec.files.clear" \
-	    -e     "spec.extensions.clear" \
-	    -e     "src = spec.to_ruby" \
-	    -e     "src.sub!(/^$$/) {" \
-	    -e       "%[# default: #{g} #{File.mtime(g).strftime(%[%s.%N])}\n]" \
-	    -e     "}" \
-	    -e     "File.binwrite(File.join(destdir, spec.full_name+'.gemspec'), src)" \
-	    -e   "end" \
-	    -e "end" \
-	    -- .bundle/specifications lib ext
+	$(Q)$(MINIRUBY) -W0 -C "$(srcdir)" -I tool/lib -roptparse -routput -rbundled_gem \
+	    -e "(out = Output.new).def_options(ARGV.options)" \
+	    -e "BundledGem.update_default_gemspecs(ARGV.parse!, out, quiet: $(V).zero?)" \
+	    -- -c -o .bundle/specifications lib ext
 
 install-for-test-bundled-gems: $(TEST_RUNNABLE)-install-for-test-bundled-gems
 no-install-for-test-bundled-gems: no-update-default-gemspecs
diff --git a/configure.ac b/configure.ac
index caf3475a38d0b9..cfa78394d40b7d 100644
--- a/configure.ac
+++ b/configure.ac
@@ -3538,7 +3538,7 @@ AS_IF([test x"$cross_compiling" = xyes], [
     # darwin target requires miniruby for linking ext bundles
     PREP="$PREP"' miniruby$(EXEEXT)'
   ])
-  RUNRUBY_COMMAND='$(MINIRUBY) -I`cd $(srcdir)/lib; pwd`'
+  RUNRUBY_COMMAND='$(MINIRUBY) -I`$(CHDIR) $(srcdir)/lib; pwd`'
   RUNRUBY='$(RUNRUBY_COMMAND)'
   XRUBY='$(MINIRUBY)'
   TEST_RUNNABLE=no
diff --git a/defs/gmake.mk b/defs/gmake.mk
index fd1d467a46b14a..0320f9b7d553fb 100644
--- a/defs/gmake.mk
+++ b/defs/gmake.mk
@@ -411,6 +411,7 @@ $(srcdir)/.bundle/gems:
 
 ifneq ($(DOT_WAIT),)
 up:: $(DOT_WAIT) after-update
+after-update:: MINIRUBY = $(BASERUBY)
 endif
 
 ifneq ($(filter update-bundled_gems refresh-gems,$(MAKECMDGOALS)),)
diff --git a/tool/lib/bundled_gem.rb b/tool/lib/bundled_gem.rb
index 22d03112ed1e0f..ca9b40875c2fa5 100644
--- a/tool/lib/bundled_gem.rb
+++ b/tool/lib/bundled_gem.rb
@@ -130,4 +130,30 @@ def checkout(gemdir, repo, rev, git: $git)
     command = "#{git} checkout --detach #{rev}"
     system(command, chdir: gemdir) or raise "failed: #{command}"
   end
+
+  def load_gemspec(g)
+    dir, base = File.split(g)
+    spec = Dir.chdir(dir) {Gem::Specification.load(base)} || Gem::Specification.load(g) or
+      return false
+    spec.files.clear
+    spec.extensions.clear
+    src = spec.to_ruby
+    src.sub!(/^$$/) {
+      %[# default: #{g} #{File.mtime(g).strftime(%[%s.%N])}\n]
+    }
+    return spec.full_name+'.gemspec', src
+  end
+
+  def update_default_gemspecs(basedirs, out, quiet: true)
+    basedirs.each do |basedir|
+      Dir.glob(basedir+'/**/*.gemspec') do |g|
+        name, src = BundledGem.load_gemspec(g)
+        unless src
+          puts "Ignoring #{g}" unless quiet
+          next
+        end
+        out.write(src, name: name, newer: File.mtime(g), quiet: quiet)
+      end
+    end
+  end
 end
diff --git a/tool/lib/output.rb b/tool/lib/output.rb
index 8cb426ae4af69b..8590e0ffe21c96 100644
--- a/tool/lib/output.rb
+++ b/tool/lib/output.rb
@@ -31,8 +31,8 @@ def def_options(opt)
     @vpath.def_options(opt)
   end
 
-  def write(data, overwrite: @overwrite, create_only: @create_only)
-    unless @path
+  def write(data, overwrite: @overwrite, create_only: @create_only, name: nil, newer: nil, quiet: false)
+    unless (name = name ? (@path ? File.join(@path, name) : name) : @path)
       $stdout.print data
       return true
     end
@@ -41,20 +41,21 @@ def write(data, overwrite: @overwrite, create_only: @create_only)
     updated = color.fail("updated")
     outpath = nil
 
-    if (@ifchange or overwrite or create_only) and (@vpath.open(@path, "rb") {|f|
+    if (@ifchange or overwrite or create_only or newer) and (@vpath.open(name, "rb") {|f|
       outpath = f.path
+      next true if newer and f.mtime > newer
       if @ifchange or create_only
         original = f.read
         (@ifchange and original == data) or (create_only and !original.empty?)
       end
     } rescue false)
-      puts "#{outpath} #{unchanged}"
+      puts "#{outpath} #{unchanged}" unless quiet
       written = false
     else
       unless overwrite and outpath and (File.binwrite(outpath, data) rescue nil)
-        File.binwrite(outpath = @path, data)
+        File.binwrite(outpath = name, data)
       end
-      puts "#{outpath} #{updated}"
+      puts "#{outpath} #{updated}" unless quiet
       written = true
     end
     if timestamp = @timestamp
diff --git a/tool/rdoc-srcdir b/tool/rdoc-srcdir
index 67d024fc0be9b4..bc5e6c4e9e0020 100755
--- a/tool/rdoc-srcdir
+++ b/tool/rdoc-srcdir
@@ -1,19 +1,8 @@
 #!ruby -W0
 
-srcdir = File.dirname(__dir__)
-bundled_gems = File.join(srcdir, "gems/bundled_gems")
-versions = {}
-File.foreach(bundled_gems) do |line|
-  next if line.start_with?("#") || line.strip.empty?
-  name, version, = line.split
-  versions[name] = version
-end
-
-%w[tsort rdoc].each do |lib|
-  path = File.join(srcdir, ".bundle/gems/#{lib}-#{versions[lib]}")
-  $LOAD_PATH.unshift("#{path}/lib")
-end
+require 'rubygems'
 require 'rdoc/rdoc'
+require 'rbs'
 
 # Make only the output directory relative to the invoked directory.
 invoked = Dir.pwd
diff --git a/vcpkg.json b/vcpkg.json
index 2652e626e55a83..64d73c40481ccc 100644
--- a/vcpkg.json
+++ b/vcpkg.json
@@ -7,5 +7,5 @@
     "openssl",
     "zlib"
   ],
-  "builtin-baseline": "c3867e714dd3a51c272826eea77267876517ed99"
+  "builtin-baseline": "56bb2411609227288b70117ead2c47585ba07713"
 }
\ No newline at end of file