Born the son of Rachel Dickinson and Joseph Ferrell Dabney, Sr., Henry married Mary A. Kramer of Pennsylvania on 19 May 1875 and she died in 1881 after giving birth to two children.
In 1861 when brothers John, James and Richard left home to enlist in the CSA, 30th Virginia, Company G, Henry, age 17, apparently coveted a post alongside his siblings. In a letter to his sister Eliza, Lt. John Dabney articulated his little brother's desire, "Henry was over here last week, and told me he…dreams to see you all someday...He is anxious to join our company." Poor Henry did in fact enlist in the 30th immediately following that letter, only to be discharged one year later in August 1862 for being under age- by merely 17 days! Eventually, Henry served the CSA as a private in the 2nd Battalion, Virginia Infantry, also known as Quartermaster/Waller's Battalion, Local Defense, Company F. The 2nd combined in September 1864 with the 6th Infantry Battalion to become the 2nd Regiment, Virginia Infantry, Local Defense and he was a member of Company H. Older brother, Joseph F. Dabney Jr., was in both units with Henry, where they worked in the CS Boot Depot in Richmond as shoemakers at a rate of $2.00 per day, in addition to traditional military duties.
Henry was the Postmaster, Caroline County, city of Guinea from 22 Nov 1865 - 28 May 1866 (after his brother Charles held the position). He accepted a temporary job as a local agent for the U.S. and D., L. & W Expresses, but stayed on month after month. This position led Henry to make a permanent home in Montclair, New Jersey, where he became a very successful coal and wood dealer. In the 1891 publication of "Bloomfield and Montclair and Their Leading Business Men" by John Austin Williams, he received the following accolades, "His business career in the history of this town can be chronicled to his high credit, for in any relations…square and upright are the characteristics which have attended them. Mr. Dabney is a Southerner by birth and inclinations, and has traveled extensively throughout that portion of the U.S."
According to family lore, Henry and brother Joseph brought comrade James Henry Noland home with them to "Maple Swamp' after the war. James Noland subsequently married the youngest Dabney sister, Tomasia. Written impressions by grandniece, Mildred Trussell Frye, "Henry was the devoted older and wealthy brother of Tomasia, who occasionally came to visit her at our home...such a lady and gentleman had to come from something good."