Insurance coverage for evidence-based smoking cessation treatments (SCTs) promotes uptake and reduces smoking rates. Published studies in this area are based in the US where employers are the primary source of health insurance. In Ontario, Canada, publicly funded healthcare does not cover SCTs, but it can be supplemented with employer-sponsored benefit plans. This study explores factors affecting the inclusion/exclusion of smoking cessation (SC) benefits. In total, 17 interviews were conducted with eight employers (auto, retail, banking, municipal and university industries), four health insurers, two government representatives and three advisors/consultants. Overall, SCT coverage varied among industries; it was inconsistently restrictive and SCT differed by coverage amount and length of use. Barriers impeding coverage included the lack of the following: Canadian-specific return on investment (ROI), SC cost information, employer demand, government regulations/incentives and employee awareness of and demand. A Canadian evidence-based calculation of ROI for SC coupled with government incentives and public education may be needed to promote uptake of SCT coverage by employers.