diff --git a/.github/workflows/mingw-w64.yml b/.github/workflows/mingw-w64.yml
index ea21e759cd81..7ad606bbb53e 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@61f9e5e925871ba6c9e3e8da24ede83ea27fa91f # v2.27.0
+        uses: msys2/setup-msys2@40677d36a502eb2cf0fb808cc9dec31bf6152638 # v2.28.0
         with:
           msystem: UCRT64
           update: true
@@ -70,11 +70,11 @@ jobs:
           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@61f9e5e925871ba6c9e3e8da24ede83ea27fa91f # v2.27.0
+        uses: msys2/setup-msys2@40677d36a502eb2cf0fb808cc9dec31bf6152638 # v2.28.0
         with:
           msystem: UCRT64
           update: true
@@ -99,12 +99,12 @@ jobs:
           make std_spec
 
   x86_64-mingw-w64-test-compiler:
-    runs-on: windows-2022
+    runs-on: windows-2025
     needs: [x86_64-mingw-w64-build]
     steps:
       - name: Setup MSYS2
         id: msys2
-        uses: msys2/setup-msys2@61f9e5e925871ba6c9e3e8da24ede83ea27fa91f # v2.27.0
+        uses: msys2/setup-msys2@40677d36a502eb2cf0fb808cc9dec31bf6152638 # v2.28.0
         with:
           msystem: UCRT64
           update: true
@@ -185,7 +185,7 @@ jobs:
     steps:
       - name: Setup MSYS2
         id: msys2
-        uses: msys2/setup-msys2@61f9e5e925871ba6c9e3e8da24ede83ea27fa91f # v2.27.0
+        uses: msys2/setup-msys2@40677d36a502eb2cf0fb808cc9dec31bf6152638 # v2.28.0
         with:
           msystem: CLANGARM64
           update: true
@@ -259,7 +259,7 @@ jobs:
     steps:
       - name: Setup MSYS2
         id: msys2
-        uses: msys2/setup-msys2@61f9e5e925871ba6c9e3e8da24ede83ea27fa91f # v2.27.0
+        uses: msys2/setup-msys2@40677d36a502eb2cf0fb808cc9dec31bf6152638 # v2.28.0
         with:
           msystem: CLANGARM64
           update: true
diff --git a/.github/workflows/win.yml b/.github/workflows/win.yml
index 84ba190cdad1..3dd9eb56f953 100644
--- a/.github/workflows/win.yml
+++ b/.github/workflows/win.yml
@@ -16,7 +16,7 @@ env:
 
 jobs:
   x86_64-windows-libs:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -95,7 +95,7 @@ jobs:
         run: .\etc\win-ci\build-openssl.ps1 -BuildTree deps\openssl -Version 3.4.1
 
   x86_64-windows-dlls:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -184,7 +184,7 @@ jobs:
         run: .\etc\win-ci\build-openssl.ps1 -BuildTree deps\openssl -Version 3.4.1 -Dynamic
 
   x86_64-windows-llvm-dlls:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |
@@ -219,7 +219,7 @@ jobs:
       llvm_ldflags: "psapi.lib shell32.lib ole32.lib uuid.lib advapi32.lib ws2_32.lib ntdll.lib"
 
   x86_64-windows-test:
-    runs-on: windows-2022
+    runs-on: windows-2025
     needs: [x86_64-windows-release]
     steps:
       - name: Disable CRLF line ending substitution
@@ -262,7 +262,7 @@ 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
@@ -294,7 +294,7 @@ 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
diff --git a/.github/workflows/win_build_portable.yml b/.github/workflows/win_build_portable.yml
index e25ac0ea2d19..0de5e4928d95 100644
--- a/.github/workflows/win_build_portable.yml
+++ b/.github/workflows/win_build_portable.yml
@@ -20,7 +20,7 @@ permissions: {}
 
 jobs:
   build:
-    runs-on: windows-2022
+    runs-on: windows-2025
     steps:
       - name: Disable CRLF line ending substitution
         run: |