Henry Stokes Tiffen was born on 12 July 1816, and was baptised on 28 December 1817 at Hythe, Kent, England. He was the son of William Tiffen, printer, and his wife, Charlotte Stokes. He married Caroline Ellen White in Ore, Sussex, on 23 September 1841.
Trained in surveying in England, Henry Tiffen was engaged by the New Zealand Company as an assistant surveyor and arrived at Wellington on the Brougham on 9 February 1842. Caroline Tiffen died in childbirth at Wellington on 10 October that year. After the expiry of his contract in 1845, Henry took up, in partnership with James Henry Northwood, a run at Ahiaruhe in Wairarapa, which he had earlier surveyed, stocking it with 758 merino sheep imported from Sydney. In January 1849 some 3,000 sheep were driven north to Hawke's Bay, where they were run on land leased from Maori, initially at Pourere and later further inland as well. When the partnership was dissolved in 1852, Henry Tiffen took up and later purchased the 12,700 acre Homewood run, near Otane.
Leaving Homewood under the management of his brother Frederick John Tiffen, Henry Tiffen resumed surveying in the early 1850s, initially on commission. After visiting Britain in 1855–56, where he married Caroline Tiffen's older sister, Louisa Anne White, in London on 31 July 1855, Tiffen secured appointment as a Wellington provincial surveyor. From October 1856 he was in control of the Napier land office and all surveying in the district, responsibilities which he continued to bear as commissioner of Crown lands and chief provincial surveyor after the separation of Hawke's Bay province in 1858. Although he brought order to the disorganised Hawke's Bay Survey Department and was responsible for the laying out of the townships of Clive and Havelock North, staffing problems and his own heavy commitments combined to reduce his effectiveness. In the exercise of his wide discretionary powers as land commissioner, he drew criticism for being the mere instrument of runholding interests, with whom he identified. Nevertheless Tiffen emerged as an opponent of runholder acquisition of land suitable for closer settlement, especially on the Heretaunga Plain. Runholder disenchantment with his approach probably contributed to his resignation on 31 July 1863. He favoured dividing up the runs which had been created and consolidated during his commissionership, disposing of his own run, Homewood, in such a manner in the 1870s.
From 1857 Tiffen had shrewdly invested in land at Greenmeadows, near Napier, as it came on to the market. Although residing in Napier, he became a spokesman and lobbyist for Taradale–Greenmeadows settlers and was largely responsible for the construction in 1873 of the Taradale Road. He was active in the cause of flood control, and sought to demonstrate the productive capacity of the land. In addition to sheepfarming, he pursued a variety of horticultural interests in Greenmeadows, planting grapevines and an experimental orchard, and promoting such plants as sugarbeet and tobacco. From 1866 through to the 1880s he profited by subdividing parts of his property as values rose. The Tiffen blend of capitalist self-interest and improving zeal and assiduous public service was no less evident in his extensive Hawke's Bay business activities, which included shipping, goldmining, boiling down of carcasses, meat freezing, public utilities, woollen milling and fruit and vegetable processing.
Tiffen maintained a high profile in community affairs. He served on a succession of public bodies, frequently as chairman, beginning with the Napier harbour improvement commission of 1857. Elected to the first Hawke's Bay Provincial Council in 1859, he sat continuously (with a brief interruption in 1860–61) until defeated in 1875, and was chairman of committees (1859–60), member of the executive council (1861–62) and speaker (1867–71). He was first chairman (1877–78) of the Hawke's Bay County Council but failed in an attempt to enter national politics in 1877. From December 1858 he was a justice of the peace and in 1869 became a junior officer in the Napier Militia. He was prominent in the establishment of Hawke's Bay's acclimatisation, agricultural and horticultural societies, the Napier Turf Club, and the Napier Mechanics' Institute. He gave long service to the Anglican church as an administrator and benefactor, served on the hospital board, took an active interest in the administration of charitable aid, Napier prison and the cemetery, and helped found the children's home. In education his involvement over 40 years ranged from administration of Napier's first school to service as a Hawke's Bay school commissioner (1884–96).
After Louisa Tiffen died in 1875, Henry Tiffen travelled widely overseas, always on the look-out for plants or produce that might thrive in or benefit Hawke's Bay. While in Italy he contracted malaria, which troubled him intermittently until his death at Napier on 21 February 1896. He had no surviving children. His principal beneficiaries were his housekeeper-niece, with him from 1876, and a sister in Wellington.