diff --git a/.github/workflows/aarch64.yml b/.github/workflows/aarch64.yml
index 14e7c3d9f564..08709685033f 100644
--- a/.github/workflows/aarch64.yml
+++ b/.github/workflows/aarch64.yml
@@ -14,13 +14,13 @@ jobs:
     if: github.repository == 'crystal-lang/crystal'
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Build Crystal
         uses: docker://crystallang/crystal:1.13.2-alpine-84codes-build
         with:
           args: make crystal
       - name: Upload Crystal executable
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: crystal-aarch64-musl
           path: |
@@ -32,9 +32,9 @@ jobs:
     if: github.repository == 'crystal-lang/crystal'
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal-aarch64-musl
       - name: Mark downloaded compiler as executable
@@ -49,9 +49,9 @@ jobs:
     if: github.repository == 'crystal-lang/crystal'
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal-aarch64-musl
       - name: Mark downloaded compiler as executable
@@ -65,13 +65,13 @@ jobs:
     if: github.repository == 'crystal-lang/crystal'
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Build Crystal
         uses: docker://crystallang/crystal:1.13.2-ubuntu-84codes-build
         with:
           args: make crystal
       - name: Upload Crystal executable
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: crystal-aarch64-gnu
           path: |
@@ -83,9 +83,9 @@ jobs:
     if: github.repository == 'crystal-lang/crystal'
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal-aarch64-gnu
       - name: Mark downloaded compiler as executable
@@ -100,9 +100,9 @@ jobs:
     if: github.repository == 'crystal-lang/crystal'
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal-aarch64-gnu
       - name: Mark downloaded compiler as executable
diff --git a/.github/workflows/backport.yml b/.github/workflows/backport.yml
index 577e4a554652..086f83cdd126 100644
--- a/.github/workflows/backport.yml
+++ b/.github/workflows/backport.yml
@@ -19,13 +19,13 @@ jobs:
     if: github.repository_owner == 'crystal-lang' && github.event.pull_request.merged == true && (github.event_name != 'labeled' || startsWith('backport', github.event.label.name))
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v6
         with:
           ref: ${{ github.event.pull_request.head.sha }}
           token: ${{ secrets.BACKPORT_ACTION_GITHUB_PAT }}
 
       - name: Create backport PR
-        uses: korthout/backport-action@be567af183754f6a5d831ae90f648954763f17f5 # v3.1.0
+        uses: korthout/backport-action@4aaf0e03a94ff0a619c9a511b61aeb42adea5b02 # v4.2.0
         with:
           github_token: ${{ secrets.BACKPORT_ACTION_GITHUB_PAT }}
           # Config README: https://github.com/korthout/backport-action#backport-action
diff --git a/.github/workflows/docs.yml b/.github/workflows/docs.yml
index 0715a65afc27..94258f629446 100644
--- a/.github/workflows/docs.yml
+++ b/.github/workflows/docs.yml
@@ -19,7 +19,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Prepare System
         run: bin/ci prepare_system
@@ -34,7 +34,7 @@ jobs:
         run: echo "$GITHUB_SHA" > ./docs/revision.txt
 
       - name: Configure AWS Credentials
-        uses: aws-actions/configure-aws-credentials@v4
+        uses: aws-actions/configure-aws-credentials@v6
         with:
           aws-access-key-id: ${{ secrets.AWS_ACCESS_KEY_ID }}
           aws-secret-access-key: ${{ secrets.AWS_SECRET_ACCESS_KEY }}
diff --git a/.github/workflows/forward-compatibility.yml b/.github/workflows/forward-compatibility.yml
index e5d8bb16eff1..396ecd4ab3ad 100644
--- a/.github/workflows/forward-compatibility.yml
+++ b/.github/workflows/forward-compatibility.yml
@@ -52,7 +52,7 @@ jobs:
             flags: "USE_PCRE1=true"
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Prepare System
         run: bin/ci prepare_system
diff --git a/.github/workflows/interpreter.yml b/.github/workflows/interpreter.yml
index 9a6bc722cfa4..1f3991cf6eeb 100644
--- a/.github/workflows/interpreter.yml
+++ b/.github/workflows/interpreter.yml
@@ -18,7 +18,7 @@ jobs:
       image: crystallang/crystal:1.15.1-build
     name: "Test Interpreter"
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v6
 
       - name: Test interpreter_spec
         run: make interpreter_spec junit_output=.junit/interpreter_spec.xml
@@ -29,13 +29,13 @@ jobs:
       image: crystallang/crystal:1.15.1-build
     name: Build interpreter
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v6
 
       - name: Build compiler
         run: make interpreter=1 release=1
 
       - name: Upload compiler artifact
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: crystal-interpreter
           path: |
@@ -51,10 +51,10 @@ jobs:
         part: [0, 1, 2, 3]
     name: "Test std_spec with interpreter (${{ matrix.part }})"
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v6
 
       - name: Download compiler artifact
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal-interpreter
           path: .build/
@@ -72,10 +72,10 @@ jobs:
       image: crystallang/crystal:1.15.1-build
     name: "Test primitives_spec with interpreter"
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v6
 
       - name: Download compiler artifact
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal-interpreter
           path: .build/
diff --git a/.github/workflows/lint-actionlint.yml b/.github/workflows/lint-actionlint.yml
index 3aab357ee340..f95a425e7f76 100644
--- a/.github/workflows/lint-actionlint.yml
+++ b/.github/workflows/lint-actionlint.yml
@@ -11,6 +11,6 @@ jobs:
   actionlint:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v6
       - name: Check workflow files
         uses: docker://rhysd/actionlint:latest
diff --git a/.github/workflows/linux.yml b/.github/workflows/linux.yml
index 2d7852f06965..f27cd24078dd 100644
--- a/.github/workflows/linux.yml
+++ b/.github/workflows/linux.yml
@@ -34,7 +34,7 @@ jobs:
           - crystal_bootstrap_version: 1.15.1 # LATEST RELEASE
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Prepare System
         run: bin/ci prepare_system
@@ -52,7 +52,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Prepare System
         run: bin/ci prepare_system
@@ -70,7 +70,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Prepare System
         run: bin/ci prepare_system
@@ -91,7 +91,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Prepare System
         run: bin/ci prepare_system
diff --git a/.github/workflows/llvm.yml b/.github/workflows/llvm.yml
index b07b0776d9fb..5640652bba33 100644
--- a/.github/workflows/llvm.yml
+++ b/.github/workflows/llvm.yml
@@ -44,7 +44,7 @@ jobs:
     name: "LLVM ${{ matrix.llvm_version }}"
     steps:
       - name: Checkout Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Install LLVM ${{ matrix.llvm_version }}
         run: |
diff --git a/.github/workflows/macos.yml b/.github/workflows/macos.yml
index 99f178fff6f5..326667b58d30 100644
--- a/.github/workflows/macos.yml
+++ b/.github/workflows/macos.yml
@@ -25,14 +25,14 @@ jobs:
           arch: aarch64-darwin
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
-      - uses: cachix/install-nix-action@v30
+      - uses: cachix/install-nix-action@v31
         with:
           extra_nix_config: |
             experimental-features = nix-command
 
-      - uses: cachix/cachix-action@v15
+      - uses: cachix/cachix-action@v16
         with:
           name: crystal-ci
           signingKey: '${{ secrets.CACHIX_SIGNING_KEY }}'
diff --git a/.github/workflows/mingw-w64.yml b/.github/workflows/mingw-w64.yml
index d65d55f624cf..c447aac43bde 100644
--- a/.github/workflows/mingw-w64.yml
+++ b/.github/workflows/mingw-w64.yml
@@ -13,11 +13,11 @@ env:
 
 jobs:
   x86_64-mingw-w64-build:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Setup MSYS2
         id: msys2
-        uses: msys2/setup-msys2@d44ca8e88d8b43d56cf5670f91747359d5537f97 # v2.26.0
+        uses: msys2/setup-msys2@4f806de0a5a7294ffabaff804b38a9b435a73bda # v2.30.0
         with:
           msystem: UCRT64
           update: true
@@ -33,7 +33,7 @@ jobs:
           git config --global core.autocrlf false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Build Crystal
         shell: msys2 {0}
@@ -44,7 +44,7 @@ jobs:
         run: make install install_dlls deref_symlinks=1 PREFIX="$(pwd)/crystal"
 
       - name: Download shards release
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
         with:
           repository: crystal-lang/shards
           ref: v0.19.1
@@ -64,17 +64,17 @@ jobs:
           ldd bin/shards.exe | grep -iv ' => /c/windows/system32' | sed 's/.* => //; s/ (.*//' | xargs -t -i /usr/bin/install -m 0755 '{}' "$(pwd)/../crystal/bin/"
 
       - name: Upload Crystal executable
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: x86_64-mingw-w64-crystal
           path: crystal
 
   x86_64-mingw-w64-test-stdlib:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Setup MSYS2
         id: msys2
-        uses: msys2/setup-msys2@d44ca8e88d8b43d56cf5670f91747359d5537f97 # v2.26.0
+        uses: msys2/setup-msys2@4f806de0a5a7294ffabaff804b38a9b435a73bda # v2.30.0
         with:
           msystem: UCRT64
           update: true
@@ -90,7 +90,7 @@ jobs:
           git config --global core.autocrlf false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Run stdlib specs
         shell: msys2 {0}
@@ -99,11 +99,11 @@ jobs:
           make std_spec
 
   x86_64-mingw-w64-test-compiler:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Setup MSYS2
         id: msys2
-        uses: msys2/setup-msys2@d44ca8e88d8b43d56cf5670f91747359d5537f97 # v2.26.0
+        uses: msys2/setup-msys2@4f806de0a5a7294ffabaff804b38a9b435a73bda # v2.30.0
         with:
           msystem: UCRT64
           update: true
@@ -119,7 +119,7 @@ jobs:
           git config --global core.autocrlf false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Run compiler specs
         shell: msys2 {0}
diff --git a/.github/workflows/openssl.yml b/.github/workflows/openssl.yml
index 916d039430bf..8ad26a42e01a 100644
--- a/.github/workflows/openssl.yml
+++ b/.github/workflows/openssl.yml
@@ -46,7 +46,7 @@ jobs:
             repository: http://dl-cdn.alpinelinux.org/alpine/v3.20/community
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Uninstall openssl and conflicts
         run: apk del openssl-dev openssl-libs-static libxml2-static
       - name: Install ${{ matrix.pkg }}
diff --git a/.github/workflows/regex-engine.yml b/.github/workflows/regex-engine.yml
index aefb70e8f141..9963779dd3c4 100644
--- a/.github/workflows/regex-engine.yml
+++ b/.github/workflows/regex-engine.yml
@@ -32,7 +32,7 @@ jobs:
     container: crystallang/crystal:1.15.1-alpine
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Remove PCRE2
         run: apk del pcre2-dev
       - name: Assert using PCRE
@@ -47,7 +47,7 @@ jobs:
     container: crystallang/crystal:1.15.1-alpine
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
       - name: Assert using PCRE2
         run: bin/crystal eval 'abort unless Regex::Engine == Regex::PCRE2'
       - name: Assert select PCRE
diff --git a/.github/workflows/smoke.yml b/.github/workflows/smoke.yml
index 3787267167ea..b188a085a954 100644
--- a/.github/workflows/smoke.yml
+++ b/.github/workflows/smoke.yml
@@ -77,7 +77,7 @@ jobs:
 
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Build fresh compiler
         run: bin/ci with_build_env make
diff --git a/.github/workflows/wasm32.yml b/.github/workflows/wasm32.yml
index 07fc4796e3cf..fd09e5b9c998 100644
--- a/.github/workflows/wasm32.yml
+++ b/.github/workflows/wasm32.yml
@@ -17,7 +17,7 @@ jobs:
     container: crystallang/crystal:1.15.1-build
     steps:
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Install wasmtime
         uses: mwilliamson/setup-wasmtime-action@v2
diff --git a/.github/workflows/win.yml b/.github/workflows/win.yml
index 4075d6968e14..4e460bc71f49 100644
--- a/.github/workflows/win.yml
+++ b/.github/workflows/win.yml
@@ -14,7 +14,7 @@ env:
 
 jobs:
   x86_64-windows-libs:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -24,18 +24,18 @@ jobs:
         uses: ilammy/msvc-dev-cmd@0b201ec74fa43914dc39ae48a89fd1d8cb592756 # v1.13.0
 
       - name: Set up Cygwin
-        uses: cygwin/cygwin-install-action@f61179d72284ceddc397ed07ddb444d82bf9e559 # v5
+        uses: cygwin/cygwin-install-action@711d29f3da23c9f4a1798e369a6f01198c13b11a # v6
         with:
           packages: make
           install-dir: C:\cygwin64
           add-to-path: false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Cache libraries
         id: cache-libs
-        uses: actions/cache@v4
+        uses: actions/cache@v5
         with:
           path: | # openssl and llvm take much longer to build so they are cached separately
             libs/pcre.lib
@@ -78,7 +78,7 @@ jobs:
 
       - name: Cache OpenSSL
         id: cache-openssl
-        uses: actions/cache@v4
+        uses: actions/cache@v5
         with:
           path: |
             libs/crypto.lib
@@ -87,13 +87,13 @@ jobs:
           key: win-openssl-libs-3.1.0-${{ hashFiles('etc/win-ci/build-openssl.ps1') }}-msvc
       - name: Set up NASM
         if: steps.cache-openssl.outputs.cache-hit != 'true'
-        uses: ilammy/setup-nasm@13cbeb366c45c4379d3478cdcbadd8295feb5028 # v1.5.1
+        uses: ilammy/setup-nasm@72793074d3c8cdda771dba85f6deafe00623038b # v1.5.2
       - name: Build OpenSSL
         if: steps.cache-openssl.outputs.cache-hit != 'true'
         run: .\etc\win-ci\build-openssl.ps1 -BuildTree deps\openssl -Version 3.1.0
 
   x86_64-windows-dlls:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -103,18 +103,18 @@ jobs:
         uses: ilammy/msvc-dev-cmd@0b201ec74fa43914dc39ae48a89fd1d8cb592756 # v1.13.0
 
       - name: Set up Cygwin
-        uses: cygwin/cygwin-install-action@f61179d72284ceddc397ed07ddb444d82bf9e559 # v5
+        uses: cygwin/cygwin-install-action@711d29f3da23c9f4a1798e369a6f01198c13b11a # v6
         with:
           packages: make
           install-dir: C:\cygwin64
           add-to-path: false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Cache libraries
         id: cache-dlls
-        uses: actions/cache@v4
+        uses: actions/cache@v5
         with:
           path: | # openssl and llvm take much longer to build so they are cached separately
             libs/pcre-dynamic.lib
@@ -166,7 +166,7 @@ jobs:
 
       - name: Cache OpenSSL
         id: cache-openssl-dlls
-        uses: actions/cache@v4
+        uses: actions/cache@v5
         with:
           path: |
             libs/crypto-dynamic.lib
@@ -176,20 +176,20 @@ jobs:
           key: win-openssl-dlls-3.1.0-${{ hashFiles('etc/win-ci/build-openssl.ps1') }}-msvc
       - name: Set up NASM
         if: steps.cache-openssl-dlls.outputs.cache-hit != 'true'
-        uses: ilammy/setup-nasm@13cbeb366c45c4379d3478cdcbadd8295feb5028 # v1.5.1
+        uses: ilammy/setup-nasm@72793074d3c8cdda771dba85f6deafe00623038b # v1.5.2
       - name: Build OpenSSL
         if: steps.cache-openssl-dlls.outputs.cache-hit != 'true'
         run: .\etc\win-ci\build-openssl.ps1 -BuildTree deps\openssl -Version 3.1.0 -Dynamic
 
   x86_64-windows-llvm-libs:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Enable Developer Command Prompt
         uses: ilammy/msvc-dev-cmd@0b201ec74fa43914dc39ae48a89fd1d8cb592756 # v1.13.0
 
       - name: Cache LLVM
         id: cache-llvm-libs
-        uses: actions/cache@v4
+        uses: actions/cache@v5
         with:
           path: llvm
           key: llvm-libs-${{ env.CI_LLVM_VERSION }}-msvc
@@ -205,7 +205,7 @@ jobs:
           cmake "-DCMAKE_INSTALL_PREFIX=$(pwd)\..\llvm" -P cmake_install.cmake
 
   x86_64-windows-llvm-dlls:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -215,11 +215,11 @@ jobs:
         uses: ilammy/msvc-dev-cmd@0b201ec74fa43914dc39ae48a89fd1d8cb592756 # v1.13.0
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Cache LLVM
         id: cache-llvm-dlls
-        uses: actions/cache@v4
+        uses: actions/cache@v5
         with:
           path: |
             libs/llvm_VERSION
@@ -238,7 +238,7 @@ jobs:
       llvm_version: "18.1.1"
 
   x86_64-windows-test:
-    runs-on: windows-2022
+    runs-on: windows-2025
     needs: [x86_64-windows-release]
     steps:
       - name: Disable CRLF line ending substitution
@@ -249,16 +249,16 @@ jobs:
         uses: ilammy/msvc-dev-cmd@0b201ec74fa43914dc39ae48a89fd1d8cb592756 # v1.13.0
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal
           path: build
 
       - name: Restore LLVM
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: llvm
           key: llvm-libs-${{ env.CI_LLVM_VERSION }}-msvc
@@ -286,7 +286,7 @@ jobs:
         run: make -f Makefile.win samples
 
   x86_64-windows-test-interpreter:
-    runs-on: windows-2022
+    runs-on: windows-2025
     needs: [x86_64-windows-release]
     steps:
       - name: Disable CRLF line ending substitution
@@ -294,16 +294,16 @@ jobs:
           git config --global core.autocrlf false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal
           path: build
 
       - name: Restore LLVM
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: llvm
           key: llvm-libs-${{ env.CI_LLVM_VERSION }}-msvc
@@ -322,7 +322,7 @@ jobs:
 
   x86_64-windows-installer:
     if: github.repository_owner == 'crystal-lang' && (startsWith(github.ref, 'refs/tags/') || startsWith(github.ref, 'refs/heads/ci/'))
-    runs-on: windows-2022
+    runs-on: windows-2025
     needs: [x86_64-windows-release]
     steps:
       - name: Disable CRLF line ending substitution
@@ -330,16 +330,16 @@ jobs:
           git config --global core.autocrlf false
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Download Crystal executable
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v8
         with:
           name: crystal
           path: etc/win-ci/portable
 
       - name: Restore LLVM
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: llvm
           key: llvm-libs-${{ env.CI_LLVM_VERSION }}-msvc
@@ -359,7 +359,7 @@ jobs:
           iscc.exe crystal.iss
 
       - name: Upload Crystal installer
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: crystal-installer
           path: etc/win-ci/Output/crystal-setup.exe
diff --git a/.github/workflows/win_build_portable.yml b/.github/workflows/win_build_portable.yml
index 398705ed21b5..a824be24675c 100644
--- a/.github/workflows/win_build_portable.yml
+++ b/.github/workflows/win_build_portable.yml
@@ -14,7 +14,7 @@ permissions: {}
 
 jobs:
   build:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -30,10 +30,10 @@ jobs:
           crystal: "1.15.1"
 
       - name: Download Crystal source
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
 
       - name: Restore libraries
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: |
             libs/pcre.lib
@@ -48,7 +48,7 @@ jobs:
           key: win-libs-${{ hashFiles('.github/workflows/win.yml', 'etc/win-ci/*.ps1') }}-msvc
           fail-on-cache-miss: true
       - name: Restore OpenSSL
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: |
             libs/crypto.lib
@@ -57,7 +57,7 @@ jobs:
           key: win-openssl-libs-3.1.0-${{ hashFiles('etc/win-ci/build-openssl.ps1') }}-msvc
           fail-on-cache-miss: true
       - name: Restore DLLs
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: |
             libs/pcre-dynamic.lib
@@ -81,7 +81,7 @@ jobs:
           key: win-dlls-${{ hashFiles('.github/workflows/win.yml', 'etc/win-ci/*.ps1') }}-msvc
           fail-on-cache-miss: true
       - name: Restore OpenSSL DLLs
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: |
             libs/crypto-dynamic.lib
@@ -91,13 +91,13 @@ jobs:
           key: win-openssl-dlls-3.1.0-${{ hashFiles('etc/win-ci/build-openssl.ps1') }}-msvc
           fail-on-cache-miss: true
       - name: Restore LLVM
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: llvm
           key: llvm-libs-${{ inputs.llvm_version }}-msvc
           fail-on-cache-miss: true
       - name: Restore LLVM DLLs
-        uses: actions/cache/restore@v4
+        uses: actions/cache/restore@v5
         with:
           path: |
             libs/llvm_VERSION
@@ -124,7 +124,7 @@ jobs:
           make -f Makefile.win -B ${{ inputs.release && 'release=1' || '' }} interpreter=1
 
       - name: Download shards release
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
         with:
           repository: crystal-lang/shards
           ref: v0.19.1
@@ -145,7 +145,7 @@ jobs:
           cp README.md crystal/
 
       - name: Upload Crystal binaries
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: crystal
           path: crystal