Socialite and businesswoman Ivanka Trump's stalker is in trouble with the law again after previously serving six months behind bars for pestering the former model.

Justin Massler, 32, has been named in court papers filed by Trump after he reportedly sent the brother of Trump’s husband, Joshua Kushner, an email in violation of a restraining order.

The convicted stalker also travelled to New York without permission.

In 2012, Massler pleaded guilty to sending Trump YouTube videos and emails, and visiting her Madison Avenue, New York jewellery store and served six months in jail.