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On that ill-fated day, Allen was scheduled to transport medical cargo from Jackson, Mississippi, to Birmingham, Alabama. His wife, Cie, aged 46, joined him on the trip as a unique Valentine’s Day gesture. The primary issue was that Allen, despite having a valid instrument rating, had not been cleared for instrument (IFR) flights with his company. He was only authorized to fly under visual flight rules (VFR) and lacked the night flying experience required to safely operate the aircraft conditions he faced. Records showed he hadn't flown at night in over three months prior to the accident.