After completing his sentence, he relocated to London and then New York, where he established a successful career as a writer of short stories and novels.

[1] He initially gained employment as a publisher's clerk for The Evening News,[3] before becoming a mail carrier in Rockdale in 1892 and a postal assistant on Oxford Street in 1895.

[1] Dwyer, with aspirations of travel and adventure, went to Melbourne with his friend Joseph Miller, a boilermaker, intending to make money taking bets on the Caulfield Cup.

Miller confessed, saying that Dwyer was the mastermind of a scheme to make 65 fraudulent orders and cash them at suburban post offices.

His handwriting was matched to that on the postal notes and envelopes, and he had previously warned his superiors about the possibility of such a scheme in an attempt to impress them.

[6] The trial of the three men was overseen by Chief Justice Frederick Matthew Darley,[6] who informed the jury he thought Dwyer was obviously guilty before they began deliberating.

[6] After finishing his period of solitary confinement, Dwyer obtained a job cataloguing books in the prison library.

[10] A friend whose sentence was nearly completed committed one of Dwyer's poems, The Boot of Fate, to memory, and said he would send it to The Bulletin upon his release.

He generally prides himself on his smartness in not letting a prisoner 'bluff' him, and doesn't take much pains to discriminate between a 'malingerer' and a really sick man.

The two struck up a friendly conversation, during which Dwyer informed Darley of his difficulties finding employment and reintegrating back into society and also of his wishes to become a writer.

Darley was sympathetic, and wrote him a letter of introduction to the editor of The Sydney Morning Herald, recommending him for employment.

[16] Disheartened, that same afternoon Dwyer partook in unlicensed gambling outside a race track, and lost the last threepence he had for the week.

Nevertheless, the excitement from this new experience prompted him to write a short story about street gambling, which he submitted to the Sydney Sportsman.

The newspaper's owner, John Norton, subsequently offered him a steady job writing features for both the Sydney Sportsman and Truth.

[15] After his parole period was completed, Dwyer relocated to London in 1906, saying that "the Australian writer has no real chance in his own land", and going against advice given to him by Rudyard Kipling;[1] Dwyer had written to Kipling a few years prior, enclosing some written verses and mentioned he was thinking about coming to London.

[1] That same year, an issue of Short Stories published his full-length novel Pomegranates of Gold to critical acclaim.

[29] Dwyer and Welch settled in Pau, France, though they frequently traveled through Europe, Asia, and North Africa.

[31] After the Battle of France in 1940, Dwyer and his wife fled to Dover, New Hampshire via Spain, though they returned to Pau in September 1945.

According to a 1940 book on Australian literature by E. Morris Miller, Dwyer was "perhaps the most prolific short story writer" from Australia,[34][35] though his work reached a much wider audience internationally than in his homeland.

His obituary in the Australian literary magazine Southerly said that Dwyer had been "virtually unknown in Australia until the publication of his autobiography".