[1][3] In 1876, Penney appointed Cadet of Straits Settlement,[1][2][4] and in 1879 as Acting Coroner, Singapore.
[10][11] On 23 June 1887, he was appointed as Inspector of Schools for Straits Settlements when Mr E. C. Hill went for a long leave of absence[11] and in 1889, he was the Acting Assistant Colonial Secretary.
[12] On 4 July 1890, he was promoted to Senior District Officer (Province Wellesley) and continue as Acting Assistant Colonial Secretary.
[13] On 12 April 1897, he was appointed Acting Colonial Treasurer and Collector of Stamp Duties[14] and member of the Legislative Council[15] as a consequence of the death of Mr H. A. O'Brien (Acting Colonial Treasurer) and continued as Senior District Officer (Province Wellesley).
[2][19] On 13 April 1905, Penney took an eight and a half months leave of absence[20] and later retired in 1906 due to poor health.