Wilbur Anderson was just one month off 25 years old when he enlisted on 1 March, 1916. He had been educated at South Melbourne College, then Scotch College, East Melbourne, before attaining at Bachelor of Laws at the University of Melbourne. When he enlisted, he was a Barrister  at Law at the Supreme Court, Melbourne. He gave his home address as No 8 Flat, Victoria House, Clarendon Street, East Melbourne, the same address as his next of kin, his mother, Mrs. Annie Anderson. He later removed her as next of kin and substituted his wife, Beatrice Evelyn Anderson, living at 'Tasma', Parliament Place, Melbourne.

Wilbur Anderson also had military training: 12 months with the Melbourne University Rifles, 7 months with the AIF 2nd NCO Training School in Port Melbourne, where he passed his 3rd OTS course. Following his application to enlist, he first trainied at Royal Park, then went to Officer Training School at Duntroon, where he qualified in a competitive exam for his first appointment as a 2nd Lieutenant on 30 August, 1916. He could also speak and write French fluently. He applied for a commission in the AIF on 29 September, 1916, and was made a lieutenant with the AAMTC.

On 22 December, Wilbur Anderson embarked at Melbourne on the Peroic, landing at Devonport, England on 6 March, 1917. He left England almost immediately for France, and was posted for duty with the 2nd D.S. Column, on transfer from 1st Company, AMTS, then serving in Belgium. It was for his time there that he was awarded the Belgian Croix de Guerre for 'distinguished bravery', probably in the 3rd Battle of Ypres. He was also given leave to go back to England on 26 January, returning to service on 16 February, and transferred to the 2nd Australian Siege Battery. On 19 July, 1917, he was presented with his medal by His Majesty, the King of the Belgians. He was again on leave in the UK from 17 August, 1918, rejoining his unit on 9 October, only three weeks before the war finally came to an end. on 6 February, 1919, he disembarked at Southampton to report to Headquarters in London, before returning to Austalia from Devonport via the Anchises.

By June, 1919, he was working again as a barrister from No. 6 Selborne Chambers in Bourke St. Melbourne, but Wilbur Anderson's life was struck with tragedy in June, 1920. His wife, Beatrice, aged 27, died five days after the birth of their son, Stirling Evelyn, followed by the death of the baby, 16 days' old. He later married again, to Winifred Joyce, the manager of Cliveden Mansions. He left the bar and set up a legal practice, Cornwell and Anderson, stood unsuccessfully for the Victorian Legislative Council in 1925, standing as a Progressive Nationalist for East Yarra Province. He and Winifred later became the proprietors of Koorinya Guest House in Marysville, but ny 1943, he was again practising as a solicitor, living with Winifred at  70 Queens Rd., Melbourne He was to serve again in World War 11: Major W.S. Anderson, Directorate of Army Catering, Victoria Barracks, Melbourne, and living at Cliveden Mansions, East Melbourne.