Activation policies, especially formal upskilling, can strengthen social inequality among long-term unemployed people. Also, receiving skill-enhancing activities may be at odds with the ‘work first’ principle. Drawing on interviews with frontline workers in the Norwegian employment and welfare service (NAV), this article analyses how frontline workers handle the challenging aspects arising from activation policies in providing enabling activities to claimants who need comprehensive support. The findings suggest that frontline workers face claimants who expect to embark on an education, and on the contrary, claimants who lack motivation or capability to do so. In both cases, frontline workers are challenged in terms of experiencing contradictory expectations from policies and users and in assessing future outcomes and suitability of the services. Education activities provided by the public employment agency (PES) involves multiple policy fields and require specific competency on the part of frontline workers.