MCUBOOT
Bootloader requirement: your MCUboot must be built with serial recovery enabled. Required Kconfig in sysbuild/mcuboot.conf: CONFIG_MCUBOOT_SERIAL=y and CONFIG_BOOT_SERIAL_CDC_ACM=y, plus a mcuboot-button0 DT alias for the trigger button. See tikk-fleet's config as a reference. Without this, your device will not respond to firmware upload requests.
sysbuild/mcuboot.conf
CONFIG_MCUBOOT_SERIAL=y
CONFIG_BOOT_SERIAL_CDC_ACM=y
mcuboot-button0
When you click Continue, you'll be prompted to pick the bootloader's serial port.