Here’s what you’ll learn when you read this story:

• In 1488, Emperor Maximilian of Austria waged a war to reclaim Flanders, and while men wielded weapons on the frontline, women worked undercover.
• Ledgers of payment records provide evidence of many women who were sent to deliver letters or gather intelligence on enemy forces.
• Some women were so successful that they were given multiple (and often lucrative) assignments, comparable to modern covert ops.

Josine Hellebout. Crispine Sroys. Beatrice Cambiers. Tuenine sPepers. These are the women inked onto the crumbling pages of ledgers that kept track of financial records in medieval Flanders during its conflict with the Holy Roman Emperor Maximilian of Austria, a member of the famous Habsburg dynasty. While men seem to have led the Flemish revolt against the Habsburg Empire, these women—and others, many of whom went unnamed—operated an undercover spy ring that relayed messages in total secrecy.

Encompassing what are now parts of Belgium, France, and Germany, Flanders (not that Flanders) refused to bend the knee to Maximilian, who became regent of the Holy Roman Empire after the death of his son Philip the Fair in the late 1400s. The Habsburg ruler was unrelenting in trying to claim Flanders as his own. In response, regency councils were organized by people from cities such as Ghent, Bruges, and Ypres to seize control of their land and trade routes from Maximilian, and war erupted in 1488 and 1489. Local militias took up arms and foreign troops swarmed in to join forces with them.

Wars, however, are not only fought with weapons and firepower. Flanders needed an unnoticeable way to gather intelligence.

Enter the women of female espionage networks, who were primarily paid to deliver letters containing sensitive information. Some traveled under cover of night, while others sauntered by in broad daylight, with nobody ever thinking twice about a figure passing through. Men masquerading as women attempted to get away with being intelligence operatives, but were more easily caught. If a woman was discovered, she may have faced torture, but not prosecution, even though some of those who supported Maximilian’s regime were livid that they were not subject to more severe punishment.

“Their contributions extended beyond mere message delivery,” said historian Lisa Demets of Ghent University in Belgium, whose study on these incredible spy rings was recently published in Intelligence and National Security. “They operated as essential agents in a sophisticated network of information exchange, often traversing hostile territories and enduring harsh conditions.”

Records show that women would often travel in pairs to minimize risk, and they sometimes chose a companion who knew an unfamiliar city well to act as a guide. Some were hired only once, while others were given repeat assignments. Most carried messages, but a few functioned as the equivalent of CIA agents, gathering intelligence and reporting back.

Among the first messengers were Jeanne van Troys and an anonymous woman who traveled nearly 28 miles (45 km) north from Béthune to Ypres, with all expenses covered. Marie Mollis delivered letters out of Ypres to Béthune “on behalf of the law.” Masnien van der Muelne’s mission has almost been lost to history, except for written evidence that she had gone “to learn” something “about the French,” meaning that she was probably spying on military reinforcements sent from France. Tuenine sPepers was paid 48 shillings to “gather news about the king of the Romans” (code for Maximilian) and she later traveled to Diksmuide “to understand the situation there.”

Crispine Sroys also undertook several assignments in 1488 and 1489. She was sent east of Ypres to “gather news about the Germans who were said to be there.” Beatrice Cambiers and another anonymous woman were were sent to Sint-Winoksbergen, possibly to find out what was happening in Dunkirk. Cambiers would go on to receive several more assignments.

Arguably the most prolific of all was Josine Hellebout, who began espionage operations in the spring of 1489 and survived many treks through hostile territory. Her eleven assignments ranged from seeking political support to snooping on where enemy troops were stationed and how they were moving. Demets equates her with “early modern undercover agents.”

“Women’s roles during this period were not incidental but integral to the broader strategies employed by Flanders’ cities,” she said. “Their involvement in intelligence work not only underscores the complexities of late medieval conflict but also contributes to a more nuanced understanding of the social and gender dynamics of the time.”