The Darién Gap (Spanish: Región del Darién or Tapón del Darién) is a break in the Pan-American Highway consisting of a large swath of undeveloped swampland and forest within Panama‘s Darién Province in Central America and the northern portion of Colombia‘s Chocó Department in South America. The gap begins in Yaviza, Panama and ends in Turbo, Colombia, stretching between 100 km and 160 km (60–100 miles) long. Roadbuilding through this area is expensive, and the environmental cost is high. Political consensus in favor of road construction has not emerged. Consequently, there is no road connection through the Darién Gap connecting North America with South America and it is the missing link of the Pan-American Highway.
So, there is this long highway (or caravan route, or trade network) with this single treacherous gap to cross. In this case, there’s all sorts of dangerous wildlife (zero, two, four, and six-legged… but nothing robotic yet) to worry about.
The idea can certainly be transplanted into space, or even just brought to a different world. “Time to build that road… and someone has to provide security…”
The Darién Gap is subject to the presence and activities of the Marxist Revolutionary Armed Forces of Colombia (FARC), which has committed assassinations, kidnappings, and human rights violations during its decades-long insurgency against the Colombian government. FARC rebels are present on both the Colombian and Panamanian sides of the border. In 2000, two British travelers, Tom Hart Dyke and Paul Winder, were kidnapped by suspected FARC guerillas in the Darién Gap while hunting for rare orchids, a plant for which Dyke has a particular passion. The two were held captive for nine months and threatened with death before eventually being released unharmed and without a ransom being paid. Dyke and Winder later documented their experience in the book The Cloud Garden and an episode of Locked Up Abroad.
In 2003, Robert Young Pelton, on assignment for National Geographic Adventure magazine, and two traveling companions, Mark Wedeven and Megan Smaker, were detained for one week by the United Self-Defense Forces of Colombia, a pro-government paramilitary organization, in a highly publicized incident.
From May 2013, Colombian neo-paramilitary forces were reported to be very active in the Darién around Los Katios National Park and the Cuenca Cacarica  In 2013, Swedish backpacker Jan Philip Braunisch disappeared in the area after leaving the Colombian town of Riosucio with the intention of attempting a crossing on foot to Panama, via the Cuenca Cacarica. His skeletal remains were recovered in June 2015 with evidence he had been killed with a shot in the head. The FARC admitted to killing him, confusing him for a foreign spy.
Naturally, it’s easy to over-prepare for violent hostilities, when it’s some snake with a 10-minutes-to-death toxin that does the PC in: a total newbie (or even a vet that doesn’t know how to handle himself) can starve to death in the jungle, if the food supplies get spoiled or stolen by who/whatever…
And all this is on Earth, and not some alien world…