System, methods, and other embodiments described herein relate to transitioning a vehicle from an autonomous to a manual driving mode. One embodiment analyzes data from one or more vehicle sensors to detect, at a current vehicle position, features in a first detection region and a second detection region ahead of the vehicle; determines, for each of one or more hypothetical vehicle positions, which features detected at the current position, if any, lie within the first detection region at that hypothetical position; identifies, among the one or more hypothetical positions, at least one localization-failure position at which localization of the vehicle will fail due to insufficient features being detected within the first detection region at the at least one localization-failure position; and initiates a transition from the autonomous driving mode to the manual driving mode based, at least in part, on the at least one localization-failure position.