A householder challenged an intruder when he returned to find him raiding his home.
The 61-year-old man was threatened by the robber, who fled with treasured jewellery.
He was unhurt but shaken by the frightening encounter in his Cupar flat.
Police have renewed an appeal for information about the housebreaking.
The culprit forced entry to the ground floor property in Station Road on Thursday, September 22, shortly before the occupant returned home at around 11.40am.
Two jewellery boxes containing items estimated to be worth a four-figure sum were taken, some of the pieces engraved.
Photographs have now been issued of a watch stolen, in the hope that someone will recognise it.
PC Kristin Bellingham, of Cupar Police Station, said: “As well as the monetary value, the stolen items are of great sentimental value to the owners and we’re eager to return them.
“Our enquiries into the housebreaking continue and we’re continuing to appeal for the public’s help as part of this.
“Anyone who saw suspicious behaviour in the area at this time, or who recognises the description of the suspect, is urged to get in touch.
“Likewise, anyone who may have information on the whereabouts of the stolen items is asked to come forward.”
The suspect is described as white, aged 20 to 30, 5ft 8 or 9 in tall, slim with short brown hair and glasses.
He was wearing a dark blue zipped hooded top, light grey tracksuit trousers and white trainers.
Those with information are urged to call Police Scotland on 101 or Crimestoppers on 0800 555 111.
