The English captains in 1548 knew St Monans well. In the year 1544 the Fife harbours along this coastline were put under fierce cannonade from the English fleet in the first wave of the "rough wooing". St Monans harbour was attacked by an English sea force under the command of Captain Nicholas Poyntz, who had already attacked and damaged the harbours of Kinghorn, Queensferry and Burntisland. When the fleet reached St Monans, Nicholas on board a mighty galleon called the Great Galley fired on the harbour with heavy cannon. He destroyed and sank the entire fishing fleet there, which was undefended, ruining the harbour, and then turned the guns on the abbey building, knocking great holes in the masonry. The Benedictine monks living there stood helpless as the cannons did their damage, eventually setting the place ablaze. The monastery, although extensively damaged from the English attack, was repaired over the next two years.

At the time of the "rough wooing", the harbours along this coastline were relatively undefended and offered easy practice for the English gunners. The damage to the fishing fleet would have had an enormous impact in this community, with Pittenweem the twelfth richest area of Scotland at that time. The locals realised that preparations had to be made for this area's protection, because a further attack of the same scale was always possible while the English were still in a hostile mood. Any such attack would have to be thwarted.

By 1548 the Fife lairds were better prepared for the return of the English invader. To organize their defence they had gathered a force about them, and were ready to make a reckoning for the previous hurt the invader had done to this coastline. The two lairds of Largo, Andrew and John Wood, came from a family famed in the wars with England: they were the sons of the great admiral and defender of Scotland, Sir Andrew Wood (died 1540), who had destroyed the English in three major sea battles in the Forth during the reigns of James III and IV.

An early warning system was devised, with huge fires set along the Fife coast on the hills of Elie and the 300-metre-high Largo Law.

Once signs of invasion were afoot, these great beacons of fire were lit and the lairds of Largo and others knew the English were coming. They looked eastwards towards the sea and saw the sails of the English warships. The Scots forces, resolute in defence of their homeland, prepared themselves, armed in boiled leathers, mail and plate, and made haste towards St Monans -- the direction in which the English host seemed to be heading.