Kaʻiana, also known as Keawe-Kaʻiana-a-ʻAhuʻula,[1][2] (about 1755 – 1795[3]) was a Native Hawaiian (kānaka ʻōiwi/maoli) warrior and aliʻi (noble) of Puna, Hawai‘i,[4] who turned against Kamehameha I in 1795 during his conquest of Oahu[5] and then sided with the island's ruler, Kalanikupule.

[9][12] On March 8, 1779, either Kaʻiana-a-ʻAhuʻula or his cousin Kaʻiana Ukupe is recorded as "Taiana" traveling aboard HMS Resolution from Kauaʻi to Niʻihau on the last leg of James Cook's third and final voyage after the navigators death.

[9][13] His cousin Kaʻiana Ukupe, a son of Kaolohaka (k), was the father of Kaikioʻewa, the first governor of Kauaʻi who joined forces along with others to support Kamehameha I.

Meares also stated that he carried himself; "replete with dignity, and having lived in the habit of receiving the respect due to superior rank in his own country, he possessed an air of distinction".

The conspiracy was discovered and while many of the Maui men were killed, Kaʻiana and his brothers escaped to Kauaʻi, which was now ruled by Kamakahelei and her husband Kāʻeokūlani, a son of Kekaulike, making him a half-brother of Kahekili.

When the first Europeans to return to the islands since the death of Cook arrived, they were greeted by Kāʻeokūlani and Kaʻiana,[20][a] carrying his young daughter and accompanied by a large group of attendants.

he treated her with a fondness truly paternal, carrying her for the most part in his arms, and when fatigued, his attendants anxiously strove which should have the honour of bearing little Miss, till the father again reassumed his pretty charge".

He had passed out small presents to the women and children and was then surprised by gifts of pigs and fresh vegetables delivered to his ship from Kaʻiana.

[24] Some month before, Captain Charles William Barkley arrived at Oahʻu and took aboard his ship, the Imperial Eagle, a Native Hawaiian woman or wahine.

The ship departed for Hawaiʻi, stopping at Kawaihae, Kailua and finally docking at Kealakekua Bay where they were greeted by Kamehameha I. Kaʻiana would settle on Hawaiʻi and help Kamehameha I secure a larger arsenal of Western firearms and ammunitions from visiting foreign ships to use in his conquest of the Hawaiian Islands.

[31] In 1795, Kaʻiana and his brother were ordered by Kamehameha I to join him on his campaign against Kalanikūpule, the aliʻi nui of Maui and Oʻahu and the son and successor of Kahekili II.

[31] On Oʻahu, Kaʻiana and Nāhiʻōleʻa, dissatisfied with being excluded from Kamehameha's war council, defected to Kalanikūpule and were both killed at the Battle of Nuʻuanu in 1795.