Henry was born in France at Le Mans on 5 March 1133 as the eldest child of Geoffrey the Fair, the Count of Anjou, and the Empress Matilda, so titled because of her first marriage to Henry V, the Holy Roman Emperor. The French county of Anjou had been formed in the 10th century and the Angevin rulers had for several centuries attempted to extend their influence and power across France through careful marriages and political alliances. In theory the county answered to the French king but royal power over Anjou had weakened during the 11th century and the county had become largely autonomous. Henry's mother was the eldest daughter of Henry I, King of England and Duke of Normandy. She was born into a powerful ruling class of Normans, who traditionally owned extensive estates in both England and Normandy.[4] Matilda was married at a young age to Henry V; after his death she was remarried to Geoffrey.[5] Following Henry I's death in 1135, Matilda had hoped to claim the English throne but instead her cousin Stephen of Blois was crowned king and recognised as the Duke of Normandy, resulting in civil war between their rival supporters.[6] Geoffrey took advantage of the confusion to attack the Duchy of Normandy but played no direct role in the English conflict, leaving this to Matilda and her half-brother, Robert of Gloucester.[7] The war, termed the Anarchy by Victorian historians, dragged on and degenerated into stalemate.[8] Henry probably spent some of his earliest years in his mother's household, and accompanied Matilda to Normandy in the late 1130s.[9] Henry's later childhood, probably from the age of seven, was spent in Anjou, where he was educated by Peter of Saintes, a noted grammarian of the day.[10] In late 1142, Geoffrey decided to send the nine-year old to Bristol, the centre of Angevin opposition to Stephen in the south-west of England, accompanied by Robert of Gloucester.[11] Although having children educated in relatives' households was common among noblemen of the period, sending Henry to England also had political benefits, as Geoffrey was coming under criticism for refusing to join the war in England.[11] For about a year, Henry lived alongside Roger of Worcester, one of Robert's sons, and was instructed by a magister, Master Matthew; Robert's household was known for its education and learning.[12] The canons of St Augustine's in Bristol also helped in Henry's education, and he remembered them with affection in later years.[13] Henry returned to Anjou either in 1143 or 1144, resuming his education under William of Conches, another famous academic.[14]

In response to Stephen's siege, Henry returned to England again at the start of 1153, braving winter storms.[51] Bringing only a small army of mercenaries, probably paid for with borrowed money, Henry was supported in the north and east of England by the forces of Ranulf of Chester and Hugh Bigod, and had hopes of a military victory.[52] A delegation of senior English clergy met with Henry and his advisers at Stockbridge shortly before Easter in April.[53] Details of their discussions are unclear, but it appears that the churchmen emphasised that while they supported Stephen as king, they sought a negotiated peace; Henry reaffirmed that he would avoid the English cathedrals and would not expect the bishops to attend his court.[54] In an attempt to draw Stephen's forces away from Wallingford, Henry besieged Stephen's castle at Malmesbury, and the king responded by marching west with an army to relieve it.[55] Henry successfully evaded Stephen's larger army along the River Avon, preventing Stephen from forcing a decisive battle.[56] In the face of the increasingly wintry weather, the two men agreed to a temporary truce, leaving Henry to travel north through the Midlands, where the powerful Robert de Beaumont, Earl of Leicester, announced his support for the cause.[56] Henry was then free to turn his forces south against the besiegers at Wallingford.[57] Despite only modest military successes, he and his allies now controlled the south-west, the Midlands and much of the north of England.[58] Meanwhile, Henry was attempting to act the part of a legitimate king, witnessing marriages and settlements and holding court in a regal fashion.[59] Over the next summer, Stephen massed troops to renew the siege of Wallingford Castle in a final attempt to take the stronghold.[60] The fall of Wallingford appeared imminent and Henry marched south to relieve the siege, arriving with a small army and placing Stephen's besieging forces under siege themselves.[61] Upon news of this, Stephen returned with a large army, and the two sides confronted each other across the River Thames at Wallingford in July.[61] By this point in the war, the barons on both sides were eager to avoid an open battle,[62] so members of the clergy brokered a truce, to the annoyance of both Henry and Stephen.[62] Henry and Stephen took the opportunity to speak together privately about a potential end to the war; conveniently for Henry, Stephen's son Eustace fell ill and died shortly afterwards.[63] This removed the most obvious other claimant to the throne, as while Stephen had another son, William, he was only a second son and appeared unenthusiastic about making a plausible claim on the throne.[64] Fighting continued after Wallingford, but in a rather half-hearted fashion, while the English Church attempted to broker a permanent peace between the two sides.[65] In November the two leaders ratified the terms of a permanent peace.[66] Stephen announced the Treaty of Winchester in Winchester Cathedral: he recognised Henry as his adopted son and successor, in return for Henry doing homage to him; Stephen promised to listen to Henry's advice, but retained all his royal powers; Stephen's remaining son, William, would do homage to Henry and renounce his claim to the throne, in exchange for promises of the security of his lands; key royal castles would be held on Henry's behalf by guarantors whilst Stephen would have access to Henry's castles; and the numerous foreign mercenaries would be demobilised and sent home.[67] Henry and Stephen sealed the treaty with a kiss of peace in the cathedral.[68] The peace remained precarious, however, and Stephen's second son William remained a possible future rival to Henry.[69] Rumours of a plot to kill Henry were circulating and, possibly as a consequence, Henry decided to return to Normandy for a period.[69][nb 7] Stephen, however, fell ill with a stomach disorder and died on 25 October 1154, allowing Henry to inherit the throne rather sooner than had been expected.[71]

The relationship between Henry and Richard finally dissolved into violence shortly before Henry's death. Philip held a peace conference in November 1188, making a public offer of a generous long-term peace settlement with Henry, conceding to his various territorial demands, if Henry would finally marry Richard and Alice and announce Richard as his recognised heir.[342] Henry refused the proposal, whereupon Richard himself spoke up, demanding to be recognised as Henry's successor.[342] Henry remained silent and Richard then publicly changed sides at the conference and gave formal homage to Philip in front of the assembled nobles.[343] The papacy intervened once again to try to produce a last-minute peace deal, resulting in a fresh conference at La Ferté-Bernard in 1189.[344] By now Henry was suffering from a bleeding ulcer that would ultimately prove fatal.[345] The discussions achieved little, although Henry is alleged to have offered Philip that John could marry Alice instead of Richard, reflecting the rumours circulating over the summer that Henry was considering openly disinheriting Richard.[344] The conference broke up with war appearing likely, but Philip and Richard launched a surprise attack immediately afterwards during what was conventionally a period of truce.[346] Henry was caught by surprise at Le Mans but made a forced march north to Alençon, from where he could escape into the safety of Normandy.[347] Suddenly, however, Henry turned back south towards Anjou, against the advice of his officials.[348] The weather was extremely hot, the king was increasingly ill and he appears to have wanted to die peacefully in Anjou rather than fight yet another campaign.[348] Henry evaded the enemy forces on his way south and collapsed in his castle at Chinon.[349] Philip and Richard were making good progress, not least because it was now obvious that Henry was dying and that Richard would be the next king, and the pair offered negotiations.[348] They met at Ballan, where Henry, only just able to remain seated on his horse, agreed to a complete surrender: he would do homage to Philip; he would give up Alice to a guardian and she would marry Richard at the end of the coming crusade; he would recognise Richard as his heir; he would pay Philip compensation, and key castles would be given to Philip as a guarantee.[348] Henry was carried back to Chinon on a litter, where he was informed that John had publicly sided with Richard in the conflict.[350] This desertion proved the final shock and he finally collapsed into a fever, only coming to for a few moments during which he gave confession.[350] Henry died on 6 July 1189, aged 56; the king had wished to be interred at Grandmont Abbey in the Limousin, but the hot weather made transporting his body impractical and he was instead buried at the nearby Fontevraud Abbey.[350]