1095 siege of pembroke castle where the Welsh were outsmarted again.

 funny story, The Welsh outsmarted, which wasnt a rare thing in Medieval times lol

in 1095 the Welsh began a sustained campaign of resistance. By early 1096 Hywel ap Goronwy had become one of the leaders of the Welsh revolt. That Spring he, together with Uchtryd ab Edwin and the war band of Cadwgan ap Bleddyn, laid waste the province of Penfro and strongly besieged Gerald Windsor in Pembroke castle. Unfortunately for the Welsh the wily Gerald outfoxed them and baffled, forced them to break off their siege, though they returned home with great booty. In the meantime Hywel's cousins, Gruffydd and Ifor, the sons of Idnerth ap Cadwgan, operating in Brycheiniog and Glamorgan won a great victory over a Norman force at Aber-llech in the river valley between Brecon and Swansea

(Remfry, 211)

Gerald of Wales wrote not long after of the siege

Initially this castle was built by Arnulf Montgomery, during the reign of King Henry I, from stakes and turf.  Which afterwards, on his return to England, he consigned to the care of the worthy and prudent Gerald Windsor, his constable and principal war leader, leaving it guarded by a few men.  All the Welshmen of South Wales, their manly and bellicose prince - that is Rhys ap Tewdwr, who a short time before had been slain by the treachery of his own people in Brycheiniog (Brecheinoc), leaving his son, Gruffydd, a child - surrounded the castle in siege.  It happened however, that one night, when 15 soldiers had deserted the castle and endeavoured to escape in a small boat, Gerald, the next morning, gave their esquires the arms of their lords with their fees and immediately decorated them with the belt of a knight.  Truly the inconvenience of the siege, becoming more severe as time dragged on, had finally reduced the castle to extreme famine; Gerald, feigning hope and comfort with the utmost prudence, had the last 4 remaining bacons diced and thrown from the ramparts to the enemy.  However, the next day, he ran to a more refined scheme, he made letters, sealed with his own seal, to be scattered before the court of Bishop Wilfred of St Davids, who happened to be present at that time, as if accidentally dropped.  The letters were to state that Earl Arnulf would not need to send relief to the castle for the next 4 months.  Upon hearing this, the letters being read through the army, the siege was immediately dispersed with each returning to his own home.