diff --git a/.github/actions/setup_python/action.yml b/.github/actions/setup_python/action.yml
index 96968f55636df9..d1290508ab778f 100644
--- a/.github/actions/setup_python/action.yml
+++ b/.github/actions/setup_python/action.yml
@@ -22,7 +22,6 @@ inputs:
 runs:
   using: 'composite'
   steps:
-
     - name: Check if Python is already installed (Linux)
       if: ${{ runner.os == 'Linux' }}
       shell: bash
@@ -54,13 +53,11 @@ runs:
       with:
         python-version: ${{ inputs.version }}
 
-    - if: ${{ runner.os == 'macOS' || runner.os == 'Windows' || (runner.os == 'Linux' && runner.arch != 'ARM64' && steps.check_python.outputs.installed == 'false' ) }}
+    - if: ${{ runner.os == 'macOS' || runner.os == 'Windows' || (runner.os == 'Linux' && runner.arch != 'ARM64' && steps.check_python.outputs.installed == 'false') }}
       name: Setup Python ${{ inputs.version }}
       uses: actions/setup-python@0b93645e9fea7318ecaed2b359559ac225c90a2b # v5.3.0
       with:
         python-version: ${{ inputs.version }}
-      env:
-        PIP_CACHE_DIR: ${{ inputs.self-hosted-runner == 'true' && inputs.pip-cache-path || '' }}
 
     - if: ${{ inputs.should-setup-pip-paths == 'true' && runner.os != 'Windows' }}
       name: Setup pip variables (cache and install path)
diff --git a/.github/scripts/workflow_rerun/errors_to_look_for.json b/.github/scripts/workflow_rerun/errors_to_look_for.json
index b1074fa43e7200..2a6e9529a038b8 100644
--- a/.github/scripts/workflow_rerun/errors_to_look_for.json
+++ b/.github/scripts/workflow_rerun/errors_to_look_for.json
@@ -82,5 +82,9 @@
     {
         "error_text": "Upload progress stalled",
         "ticket": 152933
+    },
+    {
+        "error_text": "because the GET request got Content-Type",
+        "ticket": 158400
     }
 ]
\ No newline at end of file
diff --git a/.github/workflows/job_build_windows.yml b/.github/workflows/job_build_windows.yml
index 7b682f208c3435..674c0bc73e9fdd 100644
--- a/.github/workflows/job_build_windows.yml
+++ b/.github/workflows/job_build_windows.yml
@@ -220,12 +220,20 @@ jobs:
             
             $pythonCommand = "py -$pyVersion -c `"import sys; print(f'{sys.executable}')`""
             $pythonExecutablePath = & cmd /c $pythonCommand
-          
+
+            $pipVersion = & $pythonExecutablePath -c "import pip; print(pip.__version__)"
+            Write-Host "Using pip version: $pipVersion for $pyVersion"
+            $env:PIP_CACHE_DIR="${{ env.PIP_CACHE_PATH }}/$pipVersion"
+            
             & $pythonExecutablePath -m pip install -r ${{ env.OPENVINO_REPO }}/src/bindings/python/wheel/requirements-dev.txt
 
-            cmake -DPython3_EXECUTABLE="$pythonExecutablePath" -DOpenVINODeveloperPackage_DIR=${{ env.BUILD_DIR }} -S ${{ env.OPENVINO_REPO }}/src/bindings/python -B "$pyBuildDir"
-            cmake --build "$pyBuildDir" --parallel --config ${{ env.CMAKE_BUILD_TYPE }}          
+            cmake -DPython3_EXECUTABLE="$pythonExecutablePath" -DOpenVINODeveloperPackage_DIR=${{ env.BUILD_DIR }} -S ${{ env.OPENVINO_REPO }}/src/bindings/python -B "$pyBuildDir" &&
+            cmake --build "$pyBuildDir" --parallel --config ${{ env.CMAKE_BUILD_TYPE }} &&          
             cmake --install "$pyBuildDir" --config ${{ env.CMAKE_BUILD_TYPE }} --prefix ${{ env.INSTALL_WHEELS_DIR }} --component python_wheels
+            if ($LASTEXITCODE -ne 0) {
+              Write-Host "Failed to build Python wheels for Python $pyVersion"
+              exit 1
+            }
           }
 
       - name: Pack Artifacts