Just after sunrise on August 21, 1863, William Clarke Quantrill and a horde of Missouri bushwhackers—some 300 or 400 strong—descended on Lawrence, Kansas. Since its founding in 1854, Lawrence had stood as a haven for abolitionism in the Border West; ergo, the guerrillas, many of whom hailed from prominent slaveholding families, utterly despised the town and its inhabitants. Quantrill’s men advanced methodically, street by street, house by house, killing and burning. All told, the guerrillas set ablaze 182 buildings (damage totaling roughly $40,000,000 today) and put nearly 200 men and boys below ground. Most of the victims never stood a chance: some were gunned down in doorways, other men corralled and executed on the street. An unluckier few took shelter in attics and cellars, only to be burned alive and charred beyond recognition.

Even though irregular violence had plagued the Missouri-Kansas borderlands all through the spring and summer of 1863, the Lawrence Massacre served as a tactical and strategic tipping point. Brigadier General and commander of the District of the Border Thomas Ewing Jr. immediately issued General Order no. 11. This now infamous and much-studied measure tried to turn war against civilians into official policy for protecting them from guerrillas. However, in compelling Ewing to adopt such a counter-intuitive approach, the Lawrence Massacre also exposed a set of fundamental issues rooted in the nature of irregular war itself: chiefly, that to be effective, a military’s counter-insurgency strategy must crack down on the civilians that make guerrilla warfare logistically possible, while simultaneously avoiding the use of draconian tactics against civilians that create new guerrillas faster than the originals can be eliminated. As contemporary strategists in the Middle East and Africa could undoubtedly attest, this conundrum is alive and well—and its endurance leads us to yet another revealing conclusion concerning what has and has not changed in the last 150 years.

Issued on August 25, 1863—just four days after Quantrill’s blitz into Kansas—General Order no. 11 decreed that “all persons living in Jackson, Cass, and Bates counties, Missouri, and in that part of Vernon included in this district, except those living within one mile of the limits of Independence, Hickman’s Mills, Pleasant Hill, and Harrisonville, and except those in that part of Kaw Township, Jackson County, north of Brush Creek and west of Big Blue, are hereby ordered to remove from their present places of residence within fifteen days from the date hereof.” Moreover, Ewing’s edict gave the Union army full rights to confiscate all grain and hay in the areas affected by the expulsion clause.

In theory, this would deliver a crushing blow to guerrillas in the field. Because the vast majority lacked any official linkage to the Confederate War Department, irregular combatants relied almost entirely on their female kinship networks—mothers, aunts, sisters, wives, and cousins—to act as quartermasters and intelligence gatherers; that is, to provide food, produce clothing, steal medicine and ammunition, and to track enemy troop movements. Within this arrangement, the household functioned as both the nerve center for guerrilla logistics and as the geographic point around which a local guerrilla unit could effectively orbit. But as the immobile part of the guerrilla equation, the household also represented a great vulnerability—and Ewing knew it. These domestic headquarters, he reasoned, couldn’t ambush a column and dematerialize into the brush like the men they supported. So after months of unsuccessfully hunting bushwhackers with conventional troops and tactics, the embattled Union commander struck at his foe from the inside-out.

In reality, the main blow landed by General Order no. 11 was to Ewing’s reputation as a commander in the Border West. The short-term alleviation of irregular violence stemming from Jackson, Cass, Bates, and Vernon counties was far outweighed by the outrage generated elsewhere in the region. On one hand, the expulsion command didn’t properly distinguish between real Rebels or innocent bystanders. So for Order no. 11 to work, the baby had to go out with the bath water. On the other hand, the order not only lacked long-term, widespread applicability—Ewing could never expel everyone—but it was ironically effective at creating new guerrillas. What better tool for recruiting previously neutral parties could Ewing have handed the likes of Quantrill?

Today, many Americans presume it was easier to deal with irregular combatants in 1863 because, “back then,” the army wasn’t bound by modern rules of engagement or subject to the scrutiny of a twenty-four-hour news cycle. (Read: held accountable for collateral damage.) Further still, they tend to imagine a past in which Americans “had the stomach” for crushing insurgents like Quantrill by whatever means necessary, mass expulsion of innocent civilians included. The popular uproar that doomed General Order no. 11, coupled with the fact that virtually all of Ewing’s peers thought it was a disaster waiting to happen, should dispel this misconception. Ewing wasn’t representative of a “gutsier” time in American history. Nor had he discovered the secret to dealing with guerrillas and been the only man willing to wield it—he was incredibly desperate.

To achieve success, true guerrilla movements aren’t held to the same standards as national armies. They don’t have to win numerous victories or occupy expansive tracts of territory. All they have to do is outlast the fighting will of their conventional opponents. Doing so depends greatly on an ability to retain the support of at least some of the civilian population. And as Ewing’s example made quite clear, military measures designed to counter a large-scale guerrilla movement by directly attacking that civilian population will generally just radicalize it and create new insurgents. Metaphorically speaking, this was not a problem that could be treated bluntly at the source because doing so would exacerbate rather than assuage its primary symptoms.

So for contemporary observers, who will inevitably look backward for strategies applicable to present-day irregular troubles in the Middle East and Africa, the takeaway is still as simple and unsatisfying now as it was in August 1863: General Order no. 11’s greatest failure was not necessarily that it relied on military force against civilians as a tactical fix for the conundrum of guerrilla war. That was a glaring misunderstanding of the situation on Ewing’s part, to be sure, but it paled in comparison to the dangerously simplistic idea that any force-based, military cure-all had ever existed in the first place.