The LoRaWAN communication protocol has gained significant adoption within commercial IoT systems through support for low power, long range transmission. LoRaWAN’s growing usage in cities and civilian infrastructure has prompted investigation into its potential usage within military systems for supporting urban operations, involving expanded research on LoRa signal coverage in the presence of urban infrastructure. Through the use of a supporting Commercial-off-the-Shelf (COTS) IoT architecture, a set of experiments were conducted in New York City aimed at testing LoRa signal coverage in both indoor and outdoor settings. Performance was compared for different transmission configurations on the North American Industrial, Scientific, and Medical (ISM) 915 MHz band. This work is seen as a key step to better understand the suitability and applicability of civilian IoT communication protocols to augment and enhance tactical C2 systems for urban operations.