A skill gap in Problem Solving in Technology-Rich Environments (PS-TRE) between U.S. Baby Boomers and younger generations has been documented in previous studies using the Programme for the International Assessment of Adult Competencies (PIAAC) Survey of Adult Skills (Rampey et al., 2016). Bringing this generation of workers up to speed in this competency area is important because older workers are a growing segment of the U.S. workforce with 13 million employees expected to be age 65 or older by 2024 (Toossi & Torpey, 2017). Workplace learning may be a solution, but few studies in adult learning document outcomes of training interventions specifically for this generation, and few if any studies explore the efficacy of informal learning to improve technology competency among Baby Boomers. By using PIAAC to study the association of nonformal and informal workplace learning with PS-TRE competency among U.S. Baby Boomers, this study directly responds to these gaps in the literature. Multiple linear regression was used to conduct this analysis. Results indicate that Baby Boomers may make significant gains in PS-TRE if they participate in an optimal amount of nonformal workplace learning (on-the-job training or seminar/workshop participation). Some caution may be warranted, however, in use of on-the-job training among workers age 60-70. Learning informally from coworkers or supervisors was not associated with significant gains in PS-TRE. An optimal amount of learning-by-doing may be beneficial in large organizations, but findings also indicate too much learning-by-doing may be detrimental. No significant differences were found between men and women, between supervisors and non-supervisors, or between workers in different economic sectors. Since this is a cross-sectional study, findings are not causal; however, future research seems most promising in exploring the impact of seminar or workshop participation on PS-TRE competency for Baby Boomers. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]