Abstract: Described herein are variations of a cortisol monitoring system, including a cortisol monitoring device. For example, a cortisol monitoring device may include a skin-penetrating microneedle array for use in measuring cortisol, such as in a continuous manner. The microneedle array may include, for example, at least one microneedle comprising a working electrode comprising a cortisol-sensing aptamer that selectively and reversibly binds to cortisol. The microneedle array may include, for example, at least one microneedle including a tapered distal portion having an insulated distal apex, and an electrode on a surface of the tapered distal portion located proximal to the insulated distal apex. At least some of the microneedles may be electrically isolated such that one or more electrodes is individually addressable.