The Highwayman is one of several indigenous aircraft to the Eastern European region. This region is less consolidated than the West due to the aftermath of the Crumbling being much more severe, and the region is still a patchwork of polities influenced by Western ones.

The Highwayman in particular, called as such by foreign sources, is associated with the Free Region of Ukraine, it's original creator before reverse-engineered copies began to appear among other regional factions.

The Free Region is one of the easternmost members of the Free Network, taking up parts of Eastern Ukraine and western Russia that curiously enough strongly overlap with it's historical predecessor. In contrast to the Iberian and Tyrrhenian Confederations, the Free Region is notably much more loosely organized as it has a more rural character. However, the Free Region of Ukraine possessed much less industry in the post-Crumbling. Combined with the geography of the region, the Free Region's military is focused on both horse and motorized cavalry in the form of armored cars and light assault vehicles; which are used to launch raids into the territory of hostile powers, harass their troops, and supply partisan movements to break up the neighboring warlords' power.

The Highwayman however is a bit of an exception: It is a development of a series of Arrow derivatives, with which it shares a similar overall shape. Notably, it swaps out the canards for a closed-wing configuration. Owing to the particularly austere manufacturing conditions available, this is a machine made to be easy to manufacture and assemble, with the biggest concession to complexity being it's retractable nosewheel undercarriage. This has allowed the design to spread far apart.

While obsolete as a fighter (role nowadays taken up by imported fighters), the Highwayman is still employed as a light attack aircraft due to it's low cost, good speed and good handling. While it's payload isn't outstanding, most current Highwaymen have been reinforced as dive bombers. On top of this, the model possesses a fairly considerable weapon armament, with two 14.5 mm VHMGs in the nose and four 7.62 mm RCMGs in the wings being the typical loadouts. Interestingly enough, actual Free Region planes use either CIR-sourced 10 mm heavy machine guns instead of this mixed arrangement, or propietary calibers (9.35 and 16 mm) that are notably made to use iron bullets fired from smoothbore barrels so that both are easier to make and, in the latter case, accomodate for the otherwise extreme barrel wear.