A tailwheel assembly (22) for an aircraft includes a ventral fin (20) including a fixed airframe portion (36) of the ventral fin and a moveable tailwheel portion (38) of the ventral fin. A tailwheel strut (28) extends through the ventral fin and includes a fixed first strut portion (44) and an extendable second strut portion (42) having the moveable tailwheel portion (38) of the ventral fin secured thereto. A tailwheel (24) is secured to the extendable second strut portion. A method of operating a tailwheel assembly for an aircraft includes extending an extendable portion of a tailwheel strut from an airframe of the aircraft. The tailwheel strut has a tailwheel secured thereto and is located at least partially in a ventral fin of the aircraft. A tailwheel portion of the ventral fin is moved away from a fixed airframe portion of the ventral fin via extension of the extendable portion of the tailwheel strut.
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