In 1485, Henry 7th came to the throne in England, aided in a small way by the Butlers of Tipperary. However his coronation was opposed by many Irish Lords, including Garrett Mór despite the fact that he had supported the previous King. When Henry looked at Ireland he did not like what he saw. For one thing, his predecessor had allowed Garrett Mór of the Kildares to gain so much power that he was now becoming a threat to the English control of the Pale itself. He also decided that English control in Ireland was pathetic and resolved to restore control to the level that the Normans had enjoyed 250 years before and decided he had to take some action in Ireland.

The situation worsened in 1487, when Henry's opponent to the throne, Edward, arrived in Dublin and received the support of the Kildares, who crowned him the rightful King of England. Henry was furious and had Garrett Mór kidnapped and sent to the Tower of London for treason. He then passed a law removing the independence of the Irish parliament in the Pale, and ordered that Ireland was to be instead ruled directly from London. However, Henry soon realised that he could not hope to control the other Lords in Ireland without the influence of the Kildares, and so grudgingly reinstated Garrett Mór as his Deputy in Ireland in 1496 . He knew that if he controlled Garrett, then he would have much more chance of spreading the Pale's control all over Ireland. Garrett was succeeded by his son Garrett Óg in 1513 who continued to rule the Pale in the name of the King, now Henry 8th. However his influence started to diminish, partly because Henry married Anne Boleyn, who was from the rival Butler family. His favour with Henry began to diminish too.

In 1533 Garrett Óg was summoned to meet the King in London. A false rumour was started that Garrett Óg had been executed, and Garrett Óg's son immediately declared that he would no longer be the King's deputy in Ireland. Although the rumour may have been deliberately started to cause the mutiny, it was quickly and ruthlessly put down. The Kildares were murdered and their castle destroyed. The Pale was expanded to include the Kildare's former kingdom (today county Kildare). From then on, the Pale was ruled by Englishmen and not Irish lords. Then Henry changed tactics. With almost no loyal supporters left amongst Irish Lords, he was forced to adopt a more peaceful policy. He held talks with many Irish Lords and most signed peace treaties that recognised Henry as their King and agreed to accept English law. In return they were allowed to live free of threats from the English. Most of the Irish lords became Earls of parts of Ireland. By using this tactic, Henry managed to gain control of most of Ireland in a very short time and with practically no violence.

In 1541, Henry went against the expressed wishes of the Pope and made himself the King of Ireland as well as England. This resulted in an increase in English immigration and settlement in Ireland.