diff --git a/.github/workflows/e2e-cache-freethreaded.yml b/.github/workflows/e2e-cache-freethreaded.yml
index 6f1a667b1..5ef351c2b 100644
--- a/.github/workflows/e2e-cache-freethreaded.yml
+++ b/.github/workflows/e2e-cache-freethreaded.yml
@@ -68,9 +68,19 @@ jobs:
           python-version: ${{ matrix.python-version }}
           cache: 'pipenv'
       - name: Install pipenv
-        run: curl https://raw.githubusercontent.com/pypa/pipenv/master/get-pipenv.py | python
-      - name: Install dependencies
-        run: pipenv install requests
+        run: python -m pip install --upgrade pip pipenv
+      - name: Install dependencies on Linux/macOS
+        if: runner.os != 'Windows'
+        run: |
+          export PIPENV_PYTHON=$(which python)
+          pipenv install requests
+      - name: Install dependencies on Windows
+        if: runner.os == 'Windows'
+        run: |
+          # Remove existing virtualenv if any
+          python -m pipenv --rm || echo "No existing env"
+          # Create fresh env using current Python
+          python -m pipenv install --python $(python -c "import sys; print(sys.executable)") requests
 
   python-poetry-dependencies-caching:
     name: Test poetry (Python ${{ matrix.python-version}}, ${{ matrix.os }})
@@ -159,9 +169,19 @@ jobs:
           cache: 'pipenv'
           cache-dependency-path: '**/pipenv-requirements.txt'
       - name: Install pipenv
-        run: curl https://raw.githubusercontent.com/pypa/pipenv/master/get-pipenv.py | python
-      - name: Install dependencies
-        run: pipenv install requests
+        run: python -m pip install --upgrade pip pipenv
+      - name: Install dependencies on Linux/macOS
+        if: runner.os != 'Windows'
+        run: |
+          export PIPENV_PYTHON=$(which python)
+          pipenv install requests
+      - name: Install dependencies on Windows
+        if: runner.os == 'Windows'
+        run: |
+          # Remove existing virtualenv if any
+          python -m pipenv --rm || echo "No existing env"
+          # Create fresh env using current Python
+          python -m pipenv install --python $(python -c "import sys; print(sys.executable)") requests
 
   python-pip-dependencies-caching-with-pip-version:
     name: Test pip (Python ${{ matrix.python-version}}, ${{ matrix.os }})
diff --git a/__tests__/data/requirements-linux.txt b/__tests__/data/requirements-linux.txt
index e8ce27a19..2dc785991 100644
--- a/__tests__/data/requirements-linux.txt
+++ b/__tests__/data/requirements-linux.txt
@@ -8,5 +8,5 @@ packaging==20.7
 pdf2image==1.12.1
 Pygments==2.6.1
 requests==2.32.4
-urllib3==2.6.0
+urllib3==2.6.3
 xlrd==1.2.0
\ No newline at end of file
diff --git a/__tests__/data/requirements.txt b/__tests__/data/requirements.txt
index cc0f0648d..250612de3 100644
--- a/__tests__/data/requirements.txt
+++ b/__tests__/data/requirements.txt
@@ -42,6 +42,6 @@ pywin32-ctypes==0.2.0
 
 requests==2.32.4
 
-urllib3==2.6.0
+urllib3==2.6.3
 
 xlrd==1.2.0
\ No newline at end of file