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Harry Penn had a wife, who tragically died while giving birth to their child, Karen. (Robotech II: The Sentinels: Reflections) Because of this, Harry was highly protective of his daughter, and also disapproved of her wishes to take part in military activities. He wanted her to be a Doctor, while she wanted to be a pilot. (Robotech II: The Sentinels: "Wedding Day") Because of this, Karen believed for much of her life that her father resented her, and even blamed her for the death of his wife. (Robotech II: The Sentinels: Reflections)
Macross Island and Days Undone
In a reverted timeline caused by the disappearance of the SDF-1 and the crash landing of Voltron Lion Force on Macross Island, Harry Penn was at an interrogation of Keith Kogane with T.R. Edwards and Roy Fokker.
to be added
Before the launch of the Pioneer Expedition, he and Emil Lang were on the Robotech Factory Satellite observing Max Sterling and Karen testing the Alpha Fighter. When Karen's Veritech malfunctioned he showed great concern for her safety. When she returned he tried to use the incident to show her she wasn't cut out for being a pilot, but she brushed him off. Despite praise from both Max and Lang, he still was not convinced. And the recommendation of her for the expedition by Dr. Lang didn't sit well with him either.