Essex had waited at Helbry, an island…

April 1599 CE

Essex had waited at Helbry, an island at the mouth of the river Dee, for favorable winds in foggy conditions on April 5; a week later he had sailed from Beaumaris after impatiently riding over Penmaen Mawr while bidding his ships to follow him—"the worst way and in the extremest wet that I have endured".

After a violent passage, he reaches Dublin on April 15 and is sworn in to office the same day, when the Archbishop of Dublin preaches a notable sermon.

Within a week of his arrival, Essex mounts a lavish pageant of English chivalry during the Garter feast at Dublin on St. George's Day, April 23.

It is intended as a pointed display of the values he feels are ignored in Elizabeth's court.

The Queen had chosen a muted version of the same ceremony at home, owing to the hardships of the war, and on hearing the reports from Dublin she decides to grant the masterships of wards—a significant source of wealth—to Cecil rather than Essex.

Essex is followed from England by the Earl of Kildare, with eighteen of the chiefs of Meath and Fingal, but their vessel founders in mid-channel, and all on board are lost.

Another English general, Arthur Chichester, lands at Dublin and marches his men to Drogheda, where Essex follows to inspect the famous twelve hundred strong Flanders regiment on parade: Essex charges them with his mounted staff, but the soldiers choose not to see the joke and stand firm, forcing Essex to pull his horse back just as his backside is pricked with a pike.

The grand strategy favored at Dublin, of attacking by land and sea simultaneously, is probably impossible with English resources, given the rumors of a fresh Armada from Spain and the consequent need to keep the warships in southern waters.

Contrary to the urgings of the Irish council, the privy council at London settles on a straight land campaign against the northern rebels, and the plan for an amphibious expedition to establish a base at Lough Foyle in O'Neill's rear in the northern province of Ulster is abandoned.

The Dublin council now advises Essex to refrain from an immediate attack on O'Neill and his fellow rebel, Hugh Roe O'Donnell.

Experience suggests that the want of forage, with lean cattle and weak draft-horses, would crucially hinder a northern campaign at this point.

Instead, it is suggested that he attack the rebel allies in the province of Leinster adjacent to Dublin, where, of the total number of rebels in arms, three thousand are reckoned to have risen out alongside eight hundred mercenaries from Ulster.

In the north O'Neill displays his strategic strength by stripping the lands bordering the Pale of all food and horses, in an attempt to forestall an expedition into Ulster.

In the south O'Neill encourages a rebellion by Edmund FitzGibbon—who had inherited the Anglo-Norman title of the White Knight and has struggled to maintain his loyalty to the crown—and others in Munster, in order to distract Essex.

In the west O'Donnell moves into Connacht, and it is believed that O'Neill will follow him and join with the White Knight.

The borders of the Pale are garrisoned with five thousand of Essex's troops, garrisons around Cork are reinforced, and more troops are absorbed in Munster by Sir Thomas Norris (acting president of this province) and at Kilkenny by the Earl of Ormond.

Sir Conyers Clifford's Connacht army is also increased to three thousand.