Prince Harry's long-wished-for return to the front line in Afghanistan gives him an early chance to redeem his image after pictures of him partying naked in Las Vegas were splashed around the world.
The 27-year-old has worked hard to shake off his wild child tag in recent years, but he often trips himself up and the snaps of him playing strip billiards during a boozy night in Sin City hardly helped his cause.
Harry, the younger son of Diana, princess of Wales, who is third in line to the throne behind his father Prince Charles and elder brother Prince William, has always had a difficult path to tread.
He has thrown himself into military and charitable duties, but his achievements have always come alongside a string of regrettable incidents that leave older royals grimacing.
However Harry's generation, which the royals are trying to reach out to, seems more at ease with his dual identity as a fun-loving prince and a serious military man.
Captain Wales, as he is known in the military, is a fully-trained army attack helicopter pilot, flying the Apache, which is designed to hunt and destroy armoured vehicles.
Harry has spent years working his way back to Afghanistan.
He served there as a frontline army officer for 10 weeks, until a media blackout broke down in 2008 and he was hastily withdrawn.
But from the relative security of a helicopter, he could return without the need for secrecy agreements.
Less than a month ago, the other side of Harry was in full flow.
His Las Vegas trip saw him larking about in a pool with US Olympic swimming champion Ryan Lochte and indulging in a spot of strip billiards with a mystery woman, who was pictured nude with him.
In an age of camera phones, his antics were soon fed to the TMZ celebrity website in the United States and seen around the world.
While British papers initially honoured the palace's pleas not to publish the photographs, The Sun tabloid, Britain's biggest-selling newspaper, decided to break ranks.
The palace said that Harry was simply letting off steam.
But his behaviour raised questions about his maturity and about his security -- at least one of the revellers snapped frolicking with him in the pool was reportedly one of his protection officers.
Though William is on course to become king, Harry's every move is scrutinised nonetheless -- and Prince Henry of Wales has done his growing up very much in public.
When he was 17 he admitted having smoked cannabis, and he was soon a regular fixture at plush London nightclubs -- with booze, cigarettes, aristocratic beauties and a scuffle outside with paparazzi the common tale.
His antics were widely viewed with amused affection until he sparked a scandal in 2005 by attending a fancy dress party wearing a mock Nazi uniform.
That threatened to block his entry into the army -- but he knuckled down and served in Afghanistan in 2007-2008.
The following year his reputation took another knock when a video he made in 2006 emerged, showing him using the derogatory term "Paki".
Since then, the prince has gradually set about improving his profile and taken on royal duties.
He won plaudits for a mature performance mixed with fun as he made a diamond jubilee tour of the Caribbean on behalf of his grandmother Queen Elizabeth II this year, even "beating" the world's fastest man Usain Bolt in a mock race.
He also represented the queen at the Olympics closing ceremony in August, his highest-profile royal engagement to date.
He made light of the Las Vegas trip at a children's charity awards event on Monday and spent Tuesday watching swimming and goalball at the Paralympic Games, a last day relaxing before what may prove to be his biggest challenge yet.