Tailer continued. He served in the provincial militia during Queen Anne's War. In 1710 he commanded a militia regiment that saw action at the capture of Port Royal, Acadia. Following the victory he went London with Francis Nicholson, the expedition's leader, where he was "bigg with expectation" of advancement. His expectations were rewarded with a commission as lieutenant governor of the Province of Massachusetts Bay, serving under Governor Joseph Dudley. He then returned to Massachusetts, where he was again active in the defense of the colonies, serving at Fort William and Mary in New Hampshire, and reporting on the frontier defenses in what is now southern Maine (but was then part of Massachusetts). In early 1711/2 he married Abigail Gillam Dudley, widow of Joseph Dudley's grandson Thomas. The couple had six children, who they raised in the old Stoughton homestead in Dorchester. Tailer joined the Ancient and Honorable Artillery Company in 1712 and was elected as its captain the same year. Acting governor of Massachusetts Tailer was elected to the Governor's Council from 1712 to 1729, and was on three separate occasions commissioned as lieutenant governor of Massachusetts. Despite his connection by marriage to the Dudleys, he had an awkward political relationship with the governor during the period of his first two commissions. A number of Anglicans in the colony, Tailer among them, were skeptical of Dudley's faith. (Dudley had been raised in the Puritan way, and had formally adopted Anglican practices while in England in the 1690s.) He and Dudley were also on opposite sides of the debate on the province's currency problems. Dudley favored the issuance of public bills of credit as a means to circumvent the inflationary issuance of paper currency that had become a serious problem by the end of Queen Anne's War in 1713, while Tailer, along with his father-in-law Nathaniel Byfield and others, favored the establishment of a private land bank, that would issue bills secured by the lands of its investors. Byfield in 1714 went to London to lobby on behalf of the land bank interests, and to seek for himself the post of governor, which was open for consideration after the accession of King George I to the throne. He was unsuccessful in acquiring the governorship, but was able to convince Colonel Elizeus Burges, who had been chosen to replace Dudley, to keep Tailer on as lieutenant governor. Burges, however, was bribed