Just as they were for her ex-husband, revelations about her relationship with convicted paedophile Jeffrey Epstein have proved highly embarrassing for Sarah, Duchess of York.
Several charities have now dropped her as a patron after it emerged she had emailed Epstein to apologise for publicly disavowing him following his conviction.
In messages dating back to 2011, the duchess described the late financier as a "steadfast, generous and supreme friend", and said sorry for criticising him in public.
However, it's far from the first time the former wife of Prince Andrew has given the Royal Family a headache.
Andrew Lownie, historian and author of Entitled: The Rise and Fall Of The House of York, joins Niall in remembering the key moments in the duchess's public life.
Audio credit: @sarahferguson15 on Instagram
Producers: Soila Apparicio, Tom Gillespie
Editor: Mike Bovill