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Flask==2.1.0 в своих зависимостях требует Werkzeug, но не конретизирует версию Werkzeug.
С другой стороны на текущий момент есть Werkzeug 3.0.0 и выше, в которой убрали что-то из обратной совместимости. Поэтмоу Flask==2.1.0 не стартует с Werkzeug 3.0.
Установка конкретной Werkzeug==2.3.7 решает проблему, я проверил