In the course of a public appearance to Lichfield Cathedral on Monday, King Charles was shouted at by a protester who asked him about Prince Andrew's relationship with disgraced financier Epstein.
The protester inquired how long the King had been known about his sibling's association with Epstein, and also questioned whether he had asked the police to "conceal" for Andrew.
Despite the heckling, there were crowds of fans and cheers for the King, who was in Staffordshire for an event.
The Duke of York's connections with Epstein have been under close examination in recent weeks. The prince, who relinquished his titles earlier this month, has strongly denied any wrongdoing.
"How long have you been aware about Prince Andrew and Epstein? Did you request the authorities to cover up for him?"
The monarch remained silent but continued greeting supporters, some of whom shouted "Long live the King". One fan can be heard asking him for a embrace.
Another woman outside the venue was also heard telling the heckler to "leave" and to "be quiet".
The controversy over Prince Andrew's links to Epstein has been revived by sexual abuse allegations detailed in Virginia Giuffre's posthumously-published book.
In the publication, Ms Giuffre claims she had sex with the prince on multiple times, including once with Jeffrey Epstein and "several other minors"
Prince Andrew, who reached a out-of-court agreement with Ms Giuffre in recent years, has repeatedly denied any wrongdoing. In a previous interview, he told a news program he did not recall meeting Ms Giuffre "ever", and that they "did not have any sort of intimate relations."
But in recent times, fresh questions have been asked about how he is able to finance his way of life despite not being a active member of the royal family.
The revelation that he has only ever paid a nominal fee on his Royal Lodge has heightened the examination over his living arrangements - even though he made large payments up front, including for improvements.
The Liberal Democrats said he should be summoned front of MPs to give testimony about his rental agreement of his lodge.
But last week, the government refused to give MPs time to debate the prince's titles or his home, despite increasing calls for scrutiny.
The royal household has not commented on whether the Duke of York might relocate of his current residence - or where he might reside.
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Brent Carlson
Brent Carlson