Oleynik has not snagged a main part in television or movies in years. According to Entertainment Weekly, she guest-starred on Psych, Without a Trace, and the wildly successful Mad Men, where she played Ken Cosgrove's fiancée. She told AMC.com that her role in the period drama was a huge thrill. "I'm such a nerd for the show, and obviously I've done a lot of TV guest work, but this is the first time I've gone into a show just being such a huge fan and having seen every single episode—with commentary—probably three times."
In 2011, she snagged a recurring role on Hawaii Five-O as Jessica Kaye, an ex-CIA analyst who helps Steve McGarrett track down his archenemy. In 2012, she started appearing on Pretty Little Liars, and in 2016, she landed in an episode of Law & Order: Special Victims Unit opposite stars Mariska Hargitay and Ice-T. Those are all pretty good gigs, but at the time of this writing, they still haven't led to any dazzling opportunities.
Perhaps Oleynik is content with guest-starring roles and doesn't want to dive back into Hollywood full-time, or perhaps she's trying but just hasn't been able to connect the dots. She told AMC, "When people recognize me from Mad Men specifically, it's just the coolest feeling…I don't really know if I'm being seen differently, but I know that, just in terms of confidence, it has helped immensely…After a long round of trying to establish myself as an adult actor…I was like, 'Yes! They don't hire bad actors on Mad Men.' It was huge sigh of relief."