[7] Sir Anthony Ughtred died in Jersey on 6 October 1534 and was buried in the chapel of St George, in the castle of Mont Orgueil.

[12][13] After the death of his step-father, John Paulet, 2nd Marquess of Winchester in 1576, Ughtred was involved in a long-running and bitter dispute with his step-brother, William Paulet, 3rd Marquess of Winchester, who accused him, as an executor of his father's will, of maladministration of the property and failure to settle the claims of a number of tenants and servants.

He maintained that the Marquess's accusations were unjust and informed Burghley that he was now virtually a prisoner in his own house and that he had been engaged on the case for seven months, which had cost him over £1,000 to the great hindrance of his "private causes", and waste of precious time.

[14] Early in 1586 the dispute came before the House of Lords, where the question of the jointure of the Dowager Marchioness was examined, and Ughtred gave evidence about his executorship.

[15] Paulet pursued the matter relentlessly for a number of years, and in 1596, out of malice, persuaded the Privy Council to dismiss Ughtred from the captaincy of Netley Castle on the ground that his long absence in Ireland had caused him to neglect his charge.

He spoke in the debate on the bill against rogues and vagabonds in this Parliament, maintaining that large sums were being laid out to little purpose on houses of correction.

In August 1582, Henry Knollys informed Sir Francis Walsingham that a Breton ship he had brought into Hampton had remained there for four years without being claimed.

A licence he had received to export 500 quarters of wheat to Portugal was cancelled owing to the political situation, however he was permitted to send the same amount to Ireland.

Unfortunately for the "undertakers", some of the lands in Munster which they were allotted were claimed by Irishmen who were not in rebellion, and the consequent lawsuits were a constant drain on any profits made by the enterprise.

In 1591 Ughtred gained a Privy Council decision in his favour over some of the property assigned to him, but two years later it was rescinded, and in 1597 the matter remained unresolved.

This gave the English authorities the opportunity to settle the province with colonists from England and Wales, who, it was hoped, would be a bulwark against further rebellions.

In reality the undertakers did not provide the required number of men necessary to defend themselves and their settlers and this would have disastrous consequences during the Irish rebellion of 1598.

As a result, when the Nine Years' War, an Irish rebellion against English rule, came to Munster in 1598, most of the settlers were chased off their lands without any resistance.

On 5 October 1598, Sir Henry Ughtred and his wife left their Irish home and fled to Limerick, fifteen miles away.