Josiah Failing (July 9, 1806 – August 14, 1877) was a businessman and the fourth mayor of Portland, Oregon, United States.

He and his son Henry, who also became a noted businessman and mayor of the city, started a general merchandising business that became very successful.

[3] Early in life he went to Albany, to learn the trade of paper stainer, and in 1824, accompanied his employer in a move to New York City.

[4] Through letters from early Baptist missionaries, Failing had been fascinated by the Oregon Country for 20 years when he moved his family there in 1851.

[5] Josiah spent less time in his store, not comfortable with the monopolistic practices used by his competitors, turning the business operations over to his son Henry.

[5] Failing's arrival coincided with a period of rapid changes and growth in Portland, and he became thoroughly identified with the city's progress, and engaged in the management of its public affairs.

[7] He was particularly concerned with education, was a member of the Portland Public Schools board from 1856-1862 and 1864-1868,[8] and devoted much of his time to their establishment and management.