Many families, despite need and eligibility, struggle to meet programme deadlines to retain critical benefits. When families fail to complete programme recertification on time, they lose needed support. While scholars have tested behavioural theories like chunking, implementation intention, and loss framing to promote programme uptake, less is known about how well-designed communications can promote continuity through successful recertification, especially where recertification entails a significant administrative burden. Further, scant evidence guides how best to frame recertification deadlines. In a randomised trial with government partners (n = 3,539), we find that sending a reminder letter informed by these behavioural theories increased the number of families maintaining participation by 14 per cent. Further, anchoring people to a deadline month may suffice to thread the motivational needle: overcoming procrastination without lowering self-efficacy by anchoring them to a specific day. Adopting the most effective letter in Washington, DC, would lead 766 more families to participate uninterrupted each year.