diff --git a/.github/workflows/contrib-tests.yml b/.github/workflows/contrib-tests.yml
index e522887691..9e93490ea7 100644
--- a/.github/workflows/contrib-tests.yml
+++ b/.github/workflows/contrib-tests.yml
@@ -29,7 +29,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [macos-latest, windows-2019]
+        os: [macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11"]
         exclude:
           - os: macos-latest
@@ -168,7 +168,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.10"]
     steps:
       - uses: actions/checkout@v4
@@ -203,7 +203,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.11"]
     steps:
       - uses: actions/checkout@v4
@@ -238,27 +238,10 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.13"]
     steps:
       - uses: actions/checkout@v4
-      - name: Setup MinGW (Windows)
-        if: runner.os == 'Windows'
-        uses: msys2/setup-msys2@v2
-        with:
-          msystem: MINGW64
-          update: true
-          install: >-
-            mingw-w64-x86_64-gcc
-            mingw-w64-x86_64-gcc-fortran
-          path-type: strict
-          location: D:\
-      - name: Add MinGW to PATH
-        if: runner.os == 'Windows'
-        run: echo "D:\msys64\mingw64\bin" | Out-File -FilePath $env:GITHUB_PATH -Encoding utf8 -Append
-      - name: Check GCC version
-        if: runner.os == 'Windows'
-        run: gcc --version
       - name: Set up Python ${{ matrix.python-version }}
         uses: actions/setup-python@v5
         with:
@@ -290,7 +273,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.13"]
     steps:
       - uses: actions/checkout@v4
@@ -317,7 +300,7 @@ jobs:
         run: |
           pytest test/agentchat/contrib/test_img_utils.py test/agentchat/contrib/test_lmm.py test/agentchat/contrib/test_llava.py test/agentchat/contrib/capabilities/test_vision_capability.py --skip-openai
       - name: Image Gen Coverage
-        if: ${{ matrix.os != 'windows-2019' && matrix.python-version != '3.13' }}
+        if: ${{ matrix.os != 'windows-latest' && matrix.python-version != '3.13' }}
         run: |
           pytest test/agentchat/contrib/capabilities/test_image_generation_capability.py --skip-openai
       - name: Upload coverage to Codecov
@@ -331,7 +314,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest
@@ -371,7 +354,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.11"]
     steps:
       - uses: actions/checkout@v4
@@ -406,7 +389,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.11"]
     steps:
       - uses: actions/checkout@v4
@@ -479,7 +462,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest
@@ -519,7 +502,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest
@@ -559,7 +542,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest
@@ -599,7 +582,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest
@@ -675,7 +658,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest
@@ -715,7 +698,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-latest, macos-latest, windows-2019]
+        os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
         exclude:
           - os: macos-latest