Background: Taft-Hartley Health and Welfare Funds ("funds") administer health insurance plans that cover approximately nine million U.S. adults. Unionized workers covered by funds work primarily in blue- and pink-collar occupations and smoke at a rate almost twice that of workers in other occupations. Most funds do not provide comprehensive coverage for tobacco cessation treatment for fund participants (workers, family members, and retirees). Purpose: This study tested a pilot intervention to increase the provision and promotion of cessation benefits among Minnesota-based funds by educating the funds' advisors. Methods: Tailored educational outreach was conducted to advisors (administrators, consultants, attorneys) of 10 Minnesota-based funds (2009-2011). Pre- and post-intervention advisor interviews measured perceptions/knowledge/attitudes about tobacco use, cessation, coverage, and promotion of benefits. Pre- and post-intervention data on benefit provision were collected from Summary Plan Descriptions (SPDs) and Summary Material Modifications (SMMs) of 10 Minnesota-based funds and 19 comparison funds in Massachusetts and Washington, and compared in 2011. SPDs/SMMs were scored on benefit adequacy, comparing services covered and the extent to which they met DHHS recommendations. Results: Minnesota-based funds provided significantly higher coverage (except for copays and pre-conditions) pre-intervention. However, there were no significant differences between Minnesota and comparison funds in rate of improvement in benefits over time. At follow-up, advisors reported a significant increase in confidence in their knowledge to address smoking issues in funds. Advisors also reported sharing intervention information with fund trustees. Conclusions: Educational strategies to influence advisors who provide guidance to fund trustees may help to increase advisors' confidence to address cessation benefit improvement.