Randy Dewitt, co-founder and CEO of Twin Peaks, goes undercover in his popular sports bar and grill chain that features provocatively dressed waitresses. While there, he enlists the help of UNDERCOVER BOSS alum Coby Brooks ("Hooters"), now one of the largest franchise owners at Twin Peaks, who shaves his head and also goes undercover as an inappropriate customer.

Steven Newman, the CEO of Loehmann's, the original specialty retailer for designer and fashion brands at discount prices, attempts to measure up despite feeling awkward about helping his female customers shop for bras on UNDERCOVER BOSS.

Jane Grote Abell, Chairman of Donatos Pizza, goes undercover in her family business and learns that the pizzas aren't the only things getting baked at one store.

Anthony Wedo, CEO of Buffets, Inc., the country's largest steak buffet chain, breaks cover when he encounters a dish washer with a nasty attitude. Also, the high-energy Boss learns to work the grill station.

Amit Kleinberger, CEO of Menchie's, a popular frozen yogurt franchise, delivers a baby calf while working as a herdsman at a dairy farm. Also, the youngest Boss featured to date in the series goes deeper undercover when he dons a Menchie's mascot uniform at a kid's birthday party.

Paul Quentel, President of Alfred Angelo, one of the largest bridal retailers in the U.S., is inspired after working with a hard-working, hearing impaired employee. Also, the boss isn't afraid to get in touch with his feminine side as he helps brides find their perfect wedding dress.

Mike Bloom, President and COO of Family Dollar Stores, one of the largest discount retail companies in the country, faces his fear of heights when learning to operate a forklift that takes him 35 feet into the air. Also, the boss nearly blows his rock 'n' roll disguise when one employee invites him to a jam session.

Travis Boersma, President and Co-Founder of Dutch Bros. Coffee, learns what keeps his high-energy coffee chain brewing when he journeys to El Salvador to work on the coffee plantation from which his company purchases their coffee beans. Also, the boss recruits a colleague to go undercover for him when he fears a familiar face may spill the beans on his mission at the company's headquarters.

Seven previously featured "Bosses" discuss the challenges they had with keeping their identity undercover. Also, they provide updates on some of their memorable employees.

Shane Evans, COO of Massage Heights, one of the largest massage chains in North America, must overcome her aversion to touching people when working as a massage therapist. Also, one store's disregard for company policy rubs Evans the wrong way.

Bruce "Two Dogs" Bozsum, Chairman of Mohegan Sun, goes undercover in the gaming, hotel and entertainment destinations as he prepares to pass the business on to the next Chairman of his Native American Tribal Council. Bozsum learns the high-stakes role of slot attending and nearly runs out of gas as he retrieves cars from the valet.

Joe DiDomizio, president and CEO of Hudson Group, works undercover at his travel retail company.

Greg Miller, CEO of the Utah Jazz, one of the most recognizable basketball organizations in the NBA, attempts to make halftime history when he works undercover with their infamous Dunk Team. Also, the boss' team spirit is put to the test when he is asked to become a human basketball hoop as a member of the Interactive Team.

For the first time on UNDERCOVER BOSS, three previously featured bosses - Amit Kleinberger, CEO of Menchie's; Randy Dewitt, Co-Founder and CEO of Twin Peaks; and Steve Greenbaum, CEO and Co-Founder of PostNet - send an employee undercover for a second look inside their companies.

Jeff Platt, CEO of Sky Zone, the world's first indoor trampoline park, jumps into action as a referee for a children's dodgeball game. On another assignment, the 29-year-old boss - the youngest in the show's history - has trouble hiding his in-depth knowledge of the company when working in community relations.