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The LocalSystem service account cannot access per-user Python installs (AppData\Local\Programs\Python\...). When a per-user install is detected, automatically install Python system-wide before proceeding. - Detect per-user Python (AppData in path) and trigger system-wide install - Extract system Python install logic into Install-PythonSystemWide function - Check winget exit code before marking install successful - Split pip install and postinstall into separate steps; pip failure is fatal, postinstall failure is a warning (service DLLs may already be registered) - Use $LASTEXITCODE check on pip rather than try/catch (external process) Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>