She was a popular subject of photographs.
Kaʻiulani returned to Hawaii in 1897. The return to a warmer climate did not help her health. She continued to deteriorate as she struggled to readjust to the tropical climate of the Hawaiian islands. However, she continued to make public appearances at the urging of her father.
With the approval of Queen Liliʻuokalani and Queen Dowager Queen Kapiolani and in compliance with the last Hawaiian constitution, Princess Kaʻiulani and Prince Kawānanakoa announced their engagement on February 3, 1898.[12]
She was now a private citizen of the Republic of Hawaii, and on August 12, 1898 became citizen of the Territory of Hawaii as the annexation finally took place. During the Annexation ceremony, the Princess and her aunt, Liliʻuokalani, along with other members of the royal family and with the heads of every Hawaiian political party, wore funeral attire and shuttered themselves within Washington Place, protesting what they considered an illegal transaction. "When the news of Annexation came it was bitterer than death to me," Princess Kaʻiulani, told the San Francisco Chronicle. "It was bad enough to lose the throne, but infinitely worse to have the flag go down..."[13]