Thomas Melville Dill was named for his seafaring paternal grandfather, who had lost his master's certificate after the wreck of the Bermudian-built Cedrine on the Isle of Wight, which had been returning the last convict labourers from the Royal Naval Dockyard in Bermuda to Britain in 1863.

The British Army maintained a large Bermuda Garrison of regular and part-time artillery and infantry units to guard the Royal Naval Dockyard, and other strategic assets in the Imperial fortress colony.

By 1914, then-Captain Dill was the Commandant, but he handed that position to a subordinate to lead the unit's First Contingent to the Western Front, receiving a temporary regular commission as a Major.

[5] Serving as part of the larger Royal Garrison Artillery draft to the front, the Bermudian contingent was strongly praised by Field Marshal Douglas Haig.

[citation needed] Dill married Ruth Rapalje Neilson (1880–1973) on 15 October 1900, and they had several children, some of whom followed him to positions of prominence in Bermuda or abroad.