The naked internet pictures showing Harry, 27, with a nude woman, is the latest gaffe in a long list of scandals that have dogged his public life.
In the past he has given his critics plenty of ammunition, from smoking cannabis as a teenager to a nightclub scuffle with a paparazzi photographer.
But recent years have seen Harry work hard to shake off his reputation as a playboy prince, earned from his regular appearances on the London nightclub scene during his early 20s.
The third-in-line to the throne has become more focused on his military career and today is more likely to be pictured in army uniform then leaving a nightclub.
Yet in the previous decade the third-in-line to the throne was not so adept at remaining out of the newspapers.
Harry was forced to apologise for describing an Asian fellow officer cadet as “our little Paki friend” when video footage emerged in 2009 of the royal making the comment during his time at Sandhurst military academy three years earlier.
Another serious error of judgment saw him attend a friend’s fancy dress birthday party wearing a swastika armband in 2005 which caused widespread outrage.
The incident happened in the run-up to the national commemorations attended by the Queen to mark the 60th anniversary of the liberation of the Auschwitz concentration camp.
Clarence House quickly issued a statement saying the young prince was sorry if he had caused any offence.
In the autumn of 2004, he was embroiled in controversy when his former Eton art teacher claimed she helped him cheat in his A-levels.
Clarence House described the allegations by sacked tutor Sarah Forsyth as “incredibly unfair” and the exam board later said there was no evidence to support the claims.
Then just a week later, Harry was pictured scuffling with a photographer outside the Pangaea nightclub in central London.
No criminal action resulted, but the paparazzi snapper’s cut lip and the pictures of an angry, red-faced Harry further dented his image.
The public’s sympathy may have been with the hounded prince, but in royal circles it was simply not the done thing.
His trips abroad have also generated some problems.
In Argentina during his double gap year after leaving Eton, there were reports of a plot to kidnap him.
In Australia, the ranch he was staying at was found and besieged by photographers, prompting close aide Mark Dyer to confront them, declaring Harry might flee the Commonwealth country if they did not leave him alone.
Harry’s first serious negative publicity happened when as a 17-year-old he was involved in under-age drinking and taking cannabis.
The News of the World broke the story and told of how the Prince of Wales had sent his youngest son on a visit to rehabilitation clinic, Featherstone Lodge in south east London, to highlight the long-term dangers of drug use.
Yet, Charles’s spin doctor Mark Bolland admitted some time later that the visit to the centre had actually taken place several months before, prior to evidence of the drug-taking being uncovered by the press.
During his schooldays, Harry was relatively sheltered from exposure to the media partly thanks to the protection of his mother.
Through an informal agreement struck in the wake of her death, the media left Harry and William alone while they finished their education.