Former US national security adviser John Bolton is the latest in a line of Donald Trump's critics to find themselves on the sharp end of charges from the US Department of Justice.

Bolton, who left the White Hose in 2021 and wrote a tell-all memoir describing Trump as unfit for office and "stunningly uninformed," has been charged with mishandling classified information.

Specifically, prosecutors allege that Bolton improperly retained and transmitted classified information to members of his family, via an AOL account.

Which, if found to be true, would be a serious security breach in itself. But what makes the situation worse is that it is alleged that Iranian hackers gained access to Bolton's personal AOL account, downloaded the sensitive documents, and threatened to extort Bolton.

In an email, the suspected hacker is said to have written:

This could be the biggest scandal since Hilary's emails were leaked, but this time on the GOP side!

Contact me before it's too late...

As CNN reports, a later message read:

Good luck Mr. Mustache!

It is unclear whether the extortionist was demanding money or anything else from Bolton to prevent the sensitive documents being leaked.

It is a serious enough security breach if a government official is sending unencrypted emails containing sensitive information to members of his family for the purposes of writing a memoir. It's even more serious if their email account is subsequently hacked.

One has to wonder what layers of security Bolton had enabled on his AOL account. Was he using a strong, hard-to-crack password? AOL provides two-step verification, but had Bolton turned it on for his account?

Ironically, Bolton criticised members of the Trump administration earlier this year when it was revealed they had used the Signal messaging app to discuss military strikes, and accidentally leaked their chat to a member of the press.

Politicians being reckless with their personal email is nothing new.

Back in 2008, US Vice Presidential candidate Sarah Palin had her Yahoo account hacked (it was later revealed that it was possible to reset her password using "secret questions" available from her Wikipedia entry).

Meanwhile, the 2016 presidential campaign was dominated with discussion about Hillary Clinton's use of a private server while secretary of state. CIA Director John Brennan had his AOL account hijacked in 2015 by a teenager who social-engineered Verizon support, US director of national intelligence James Clapper had several of his personal accounts compromised, and - in an echo of the current case involving John Bolton - Colin Powell also relied on an AOL address for unclassified but sensitive State Department communications.

John Bolton has pleaded not guilty to charges of sharing classified information.