The chairman of a performing arts school in Brooklyn has to pay an almost $500,000 verdict after he installed spying software in his estranged tobacco-heiress wife’s iPhone, the New York Post reports. Jurors ordered Crocker Coulson, Brooklyn Music School chairman, to pay Anne Resnik $200,000 in compensatory damages, $200,000 in punitive damages, and $41,500 in statutory damages—or $100 for each of the 415 days he accessed her phone between 2012 and 2014. Coulson was also ordered to pay $10,000 to Resnik’s mom, sister, and psychiatrist because he also intercepted their communications by spying on his wife.

Resnik’s divorce lawyer reportedly discovered Coulson’s spying after he found a $50 PayPal charge in his financial records for OwnSpy, a software that would let him listen in on her conversations. He also installed mSpy onto Resnik’s phone, which let him access her emails, texts, photos, and GPS data. “The court is mindful that [Coulson] probably never contemplated that his initial investment of approximately $50 of spyware would start him on this path or have such dire consequences for his financial future,” Brooklyn Supreme Court Justice Jeffrey Sunshine reportedly wrote in his ruling.