Henrietta Henderson Failing (1868-1953) was a pioneering leader of the Portland Art Association, the parent organization of the Portland Art Museum and the Museum Art School. Shortly after the association was founded in 1892, she was appointed the first executive administrator, a position she held until she resigned in 1908 due to illness. From 1910 to 1940, she was the association’s lead lecturer in art history and classical studies and was named acting director in 1939.

Failing was the oldest of Edward and Olivia Failing’s nine children and the granddaughter of Josiah Failing, Portland’s third mayor. She was the niece of two civic-benefactors, Henry Failing and Matthew Deady. She graduated from St. Helen’s Hall School at Fourth Avenue and Southwest Madison Street in Portland (the site of the present-day City Hall) and advanced her professional education largely independently. An avid reader in the arts, history, and education, she studied for a short time at Radcliffe College in Boston and at the American Schools of Classical Studies in Rome and Athens. In 1893, she attended the World's Columbian Exposition in Chicago, where she engaged in a thorough study of the fair’s exhibits.

Upon her return to Portland, Failing directed the PAA’s nascent collection, exhibition, and education efforts in the upper halls of the Portland Public Library. She organized exhibits of artworks on loan from local collectors, hosted visits by school classes and community groups, and began to build the organization’s art library. She also managed the PAA’s collection, which consisted of plaster casts of Greek and Roman sculptures and friezes and print reproductions of Western masterworks. The cast collection was by far the largest in the western United States at the time, and Failing coordinated the publication of a scholarly catalog about the collection in 1897. 

During her travels in Europe in 1902 and 1903, she visited centers of artistic training across Europe in order to develop a model for an art school in Portland. During the 1905 Lewis and Clark Centennial Exposition in Portland, Failing assisted the fair’s guest curator Frank Vincent DuMond and coordinated the PAA’s opening of its first museum and studio facility on Southwest Fifth and Taylor Streets.

Beginning in 1908, Failing took a two-year leave from the PAA due to illness. After her return, she served for three decades as the instructor for the school’s art history and theory classes, hosted visits from community groups at the museum, represented the organization in the city, and advised the Portland School Art League. A PAA publication from 1924 included an essay by Failing that was an impassioned plea for art education, not only as a specialist activity but also as a key element in human development and personal fulfillment. Her advocacy for art education for the public complemented her progressive commitment to civic and social reform and her active role in the League of Women Voters.

Failing never married and presided dutifully over Portland’s extended Failing family. She died in 1953 from age-related causes.