One of the most important aspects of cognitive health is the ability to control attention; this is also one of the aspects of cognition that typically declines with age. New methods for cognitive health coaching for older adults require new techniques for unobtrusive continuous monitoring: gathering cognitive data from everyday activities performed in the home, rather than forcing elders to leave their natural environment to undergo a battery of tests. The studies discussed herein investigated a method for unobtrusively monitoring divided attention ability through analysis of performance on a cognitive computer game called 21 Tally.