Ingoldsby, Sir Henry (1622–1701), soldier and officeholder, was the son of Sir Richard Ingoldsby, landowner, and Elizabeth Ingoldsby (née Cromwell) of Lethenborough, Buckinghamshire, England. He may have attended the Thame grammar school in Buckinghamshire (like his brother Richard Ingoldsby) before going into the army. During the English civil war he served in the parliamentarian army and reached the rank of captain by 1647 and colonel by 1649. Ingoldsby was related to Oliver Cromwell (qv) and this familial connection was of great importance during his early career. He fought in Cromwell's army as colonel of a regiment of dragoons in Ireland (1649–52) and gained a reputation as a ruthless fighter; he played a prominent role in the capture of Drogheda early in the campaign and helped to subjugate the south-western counties. As a reward for his efforts he was granted about 3,500 acres in Co. Clare as well as substantial holdings in Co. Limerick, Co. Tipperary, and elsewhere. His brother George Ingoldsby (c.1623–c.1675), who reached the rank of captain, also served in Cromwell's Irish campaign and was granted lands in the same region. Unlike many other officers who served in Cromwell's army, both Henry and George Ingoldsby decided to settle in Ireland.
Henry Ingoldsby was governor of the city of Limerick from 1653 and was made mayor in 1656 when the corporation's charter was restored. He represented the combined south-western counties in Cromwell's union parliament in 1654, 1656, and 1659 and was created a baronet by Cromwell in 1658. Ingoldsby seems to have remained loyal to the lord protectorship when it began to crumble in early 1659. But by December 1659, when Richard and Henry Cromwell (qv) had been deposed, he supported the restoration of the parliament that Cromwell had dissolved in 1653 and helped to seize Windsor castle on its behalf. He represented Kells, Co. Meath, in the general convention that met in Dublin between March and May 1660; Ingoldsby had a landed interest in this part of Meath and officers who served in his dragoon regiment were allotted lands there when they were disbanded in 1655.
The restoration of Charles II must have put Ingoldsby in an uncomfortable position. He was tainted by his close connection with the Cromwellian regime, and his brother Richard Ingoldsby had signed the death-warrant of Charles I in 1649. But Henry Ingoldsby (and his brother George) were pardoned by the new king and their lands were confirmed. Henry Ingoldsby was created a baronet on 30 August 1661 and elected MP for Co. Clare in the same year. George Ingoldsby was also made a baronet c.1670 and was appointed mayor of the city of Limerick in 1672. The Dublin government perhaps conceded that the Ingoldsbys (who were talented military strategists) were best kept as allies rather than enemies in the potentially unruly south-west of Ireland. Though outwardly loyal to the crown, Henry Ingoldsby was greatly concerned by the concessions that were made to royalists and he signed a petition (along with other prominent protestant subjects) against the act of settlement in 1664. He may even have been involved with republican conspiracies: in 1666 Thomas Blood (qv) plotted to seize Dublin castle and it was alleged that ‘Sir Henry Ingoldsby would be on horseback as soon as Blood had taken the castle’ (CSPI 1663–4, 265–6).
Henry Ingoldsby was a presbyterian and a fierce opponent of the quakers. As governor of Limerick he attempted to prohibit any citizen from harbouring quakers in their households. He married a daughter of Sir Hardress Waller (qv) (a presbyterian and one of the most important protestants to have settled in Co. Limerick before 1641). His eldest son, George, succeeded to his estates when he died in March 1701. His own brother George married Mary Gould, a local heiress, and was killed in the Dutch wars c.1675. His son Richard Ingoldsby (qv) became commander of the land forces in Ireland and a lord justice.