Anna Allen Guest was born, likely in Orange County, North Carolina, in about 1763. A resident of Wilkes County, North Carolina, she married William Guest in July 1779. Guest had already served one tour in the Wilkes County Regiment of the North Carolina Militia, and he reenlisted shortly after their marriage, serving until October 1781. While her husband was away in service, Anna Guest grew the family's crops on a 345 plot of land on the Yadkin River. Anna, her husband later recalled, "did nearly all the work in the field" during the war. Aside from her duties on the farm, Anna Guest also raised the couple's first child, Squire, who was born in about April 1780. She did so by herself, often going for months at a time without seeing her husband during this period.

William and Anna Guest eventually had at least six children together and they moved to Pickens District, South Carolina in 1785, where they resided for the rest of their lives. Following her husband's death in 1841, Anna Guest never remarried. She applied for a widow's pension first in 1845. Despite the sworn affidavit of a witness to the wedding and a family record indicating that the Guests' first son was born in 1780, the U.S. Pension Office rejected her claim on the basis that she had not sufficiently proven that she had married William Guest during the Revolutionary War. In 1846 she revised her claim to apply for a pension under the provisions of the pension act of 1836, as the Pension Office found there was adequate evidence that she had married William Guest prior to 1794. Her application was approved and she received $50 per year from 1843 until her death. In 1852 she applied to the Pension Office again requesting a readjustment, arguing that she was entitled to a larger annual sum based on the totality of her husband's service during the war, but this appeal was never granted. She died sometime after March 12, 1852.